Journal of early

modern history 21 (2017) 318-342

brill.com/jemh

Philip II of Spain and His Italian Jewish Spy

Flora Cassen
UNC Chapel Hill
[email protected]

Abstract

A bitter conflict between the Spanish and Ottoman empires dominated the second half
of the sixteenth century. In this early modern “global” conflict, intelligence played a key
role. The Duchy of Milan, home to Simon Sacerdoti (c.1540-1600), a Jew, had fallen to
Spain. The fate that usually awaited Jews living on Spanish lands was expulsion—and
there were signs to suggest that King Philip II (1527-1598) might travel down that road.
Sacerdoti, the scion of one of Milan’s wealthiest and best-connected Jewish families
had access to secret information through various contacts in Italy and North-Africa.
Such intelligence was highly valuable to Spanish forces, and Philip II was personally
interested in it. However, this required Sacerdoti to serve an empire—Spain—with a
long history of harming the Jews, and to spy on the Ottomans, widely considered as
the Jews’ supporters at the time. This article offers a reflection on Simon Sacerdoti’s
story. Examining how a Jew became part of the Spanish intelligence agency helps us
understand how early modern secret information networks functioned and sheds new
light on questions of Jewish identity in a time of uprootedness and competing loyalties.

Keywords

Jewish History – Early Modern History – Spanish-Ottoman relations – Espionage –

Diplomacy

* I would like to thank Francesca Bregoli, Melissa Bullard, Eric Dursteler, the organizers
and participants of UNC’s graduate student working group on Jewish Hispano/a, Latino/a
Studies, the anonymous readers for JEMH, and Simon Ditchfield for their helpful comments
on earlier versions of this paper.

© koninklijke brill nv, leiden, ���6 | doi 10.1163/15700658-12342526

Philip II of Spain and His Italian Jewish Spy 319

…
CALYMATH. Whom have we there? A spy?
BARABAS. Yes, my good lord, one that can spy a place
Where you may enter, and surprise the town:
My name is Barabas; I am a Jew.
Marlowe, The Jew of Malta

⸪
Introduction

In Marlowe’s play, The Jew of Malta, a Jew named Barabas tries to help the Turks
take the Island of Malta. That Marlowe’s Barabas was a spy, rather than com-
mon older anti-Jewish stereotypes—usurer, host desecrator, or blasphemer—
was a sign of the times. The sixteenth century was “the first golden age of
espionage” and saw an explosion of spying and intelligence activity.1 Nascent
centralized states were developing sophisticated intelligence networks, send-
ing and recruiting agents across Europe. The Mediterranean, theater of an
ongoing war between the Spanish Habsburg and Ottoman empires, was a hot-
bed of information exchange. Both sides relied heavily on spies: internally to
control and subdue opposition, externally to keep an edge over competing or
enemy states.
Sixteenth-century Jews lived in different political and geographic zones,
with wide-ranging networks of contacts, and were favorably positioned to
obtain information of all sorts.2 Jews also functioned as intermediaries or
middlemen between Christians, Jews, and Muslims, and people from a wide

1 Carlos Carnicer and Javier Marcos, Espias de Felipe II: Los servicios secretos del Imperio español
(Madrid, 2005), 14. The second “explosion” would be the twentieth century.
2 Historians have documented the presence of Jews in sixteenth-century trading networks.
For merchants, information represented yet another commodity that could be exchanged.
Noel Malcolm, Agents of Empire. Knights, Corsairs, Jesuits and Spies in the Sixteenth-Century
Mediterranean World (Oxford, 2015), 224-226; Eric Dursteler, Venetians in Constantinople:
Nation, Identity, and Coexistence in the Early Modern Mediterranean (Baltimore, 2006),
103-130; E. Natalie Rothman, Brokering Empire: Trans-Imperial Subjects Between Venice and
Istanbul (Ithaca, 2014), 222-224; Mercedes Garcia-Arenal and Gerard Wiegers, A Man of Three
Worlds: Samuel Pallache, a Moroccan Jew in Catholic and Protestant Europe (Baltimore, 2003).

Journal of early modern history 21 (2017) 318-342

320 cassen

variety of backgrounds all around the Mediterranean Sea.3 The situation of

Jews fits with recent historiography on the Mediterranean as a space where
individuals of different religions and cultures interacted and exchanged on
a much larger scale than previously thought.4 In this dynamic marketplace
of goods and ideas where Christians, Jews, and Muslims met on a daily basis,
relations between the Spanish and Ottoman empires nonetheless remained a
divisive matter, marred as they were by antagonistic politics, competing inter-
ests, and ongoing wars. Within the bounds of this conflictual encounter, the
position of Jews was tenuous. Although the Mediterranean was an integrated
and “connected” world, this does not necessarily mean that one’s individual
or communal identity was irrelevant, or that political conflicts played no part
in shaping this multi-cultural environment.5

3 The idea of a connected Mediterranean first put forward by Braudel has gained consid-
erable scholarly attention in the past decade. Fernand Braudel, The Mediterranean and
the Mediterranean World in the Age of Philip II (Berkeley, 1995); Peregrine Horden and
Nicholas Purcell, The Corrupting Sea: A Study of Mediterranean History (Oxford/Malden
MA, 2000); David Abulafia, The Great Sea: A Human History of the Mediterranean (London/
New York, 2011). For recent reviews on Mediterranean historiography, see John A. Marino,
“Mediterranean Studies and the Remaking of Pre-Modern Europe,” Journal of Early Modern
History 15 (2011): 385-412, and Eric R. Dursteler, “On Bazaars and Battlefields: Recent
Scholarship on Mediterranean Cultural Contacts,” Journal of Early Modern History 15 (2011):
413-434.
4 For example, the study of Venice and its contacts with the Ottoman Empire has been espe-
cially useful in revealing just how fluid religious and ethnic boundaries (once assumed to
be airtight) really were. See the recent work of Bronwen Wilson, The World in Venice: Print,
the City and Early Modern Identity (Toronto, 2005); Dursteler, Venetians in Constantinople;
Rothman, Brokering Empire.
5 This line of argumentation builds on Francesca Trivellato’s work on cross-cultural exchanges
explores “the intersection of these two extremes—the omnipresence of cross-cultural con-
tacts (some voluntary, some coerced, some a mixture of the two) and the fairly rigid norma-
tive frameworks in which these contacts took place” in the eighteenth century; F. Trivellato,
The Familiarity of Strangers. The Sephardic Diaspora, Livorno, and Cross-Cultural Trade in the
Early Modern Period (New Haven/London, 2009), 271. See also Trivellato, “The Historical and
Comparative Study of Cross-Cultural Trade,” Religion and Trade: Cross-Cultural Exchanges in
World History, 1000-1900, Francesca Trivellato, Leor Halevi, Catia Antunes, eds. (Oxford, 2014),
1-23. In a recent dissertation on spying in the sixteenth-century Mediterranean, Emrah Safa
Gurkan argued that historians working on Venice and Istanbul have pushed the idea of a con-
nected Mediterranean too far. According to him, these two world cities with long histories of
trade and exchange were the exception rather than the rule. Emrah Safa Gurkan, “Espionage
in the 16th century Mediterranean: Secret Diplomacy, Mediterranean Go-Betweens and the
Ottoman Habsburg Rivalry” (Ph.D. Diss., Georgetown University, 2012), 9-10.

Journal of early modern history 21 (2017) 318-342

Philip II of Spain and His Italian Jewish Spy 321

Europeans feared Ottoman power, and believed the Jews were on their
enemy’s side. Sixteenth-century myths, as in Marlowe’s Jew of Malta, com-
monly featured the Jews as spies for the Ottomans. The Jews’ relatively
successful ­integration into Ottoman society, as witnessed by Western trav-
elers returning from the Middle East, added to these suspicions. Nicolas de
Nicolay, a Frenchman, wrote, “Marrano Jews ousted from Spain have taught
the Turkes diverse inventions, craftes and engines of warre, as to make artil-
lerie, gun pouder, shot and other munitions.”6 Henry Blount, an English trav-
eler, commented that “every Otoman vizier kept a Jew whose experience of
Christendome, with their continuell intelligence, is thought to advise most
of that mischeife, which the Turks puts in execution against us.”7 Jews, too,
would have acknowledged their special relation with the Ottomans. For
instance, Manasseh ben Israel’s Humble Address, by which he sought to con-
vince Oliver Cromwell to readmit the Jews in England, explained how Jews
were welcomed in the Ottoman Empire and the myriad of ways this benefited
the Empire.8 Surveying English Jewish writers of the period, Nabil Matar con-
cluded, “not a single Renaissance Jewish writer in England expressed the desire
to destroy the Muslims.”9 To both Christian and Jewish observers, it seemed
natural, therefore, that, undesired and persecuted in Europe, the Jews’ loyalties
lay elsewhere, and worse: with the enemies of Christianity.
The Jews’ reputation as “Barabases” notwithstanding, this article focuses
on the story of a Milanese Jew, Simon Sacerdoti, who could be described as an
anti-Barabas: a spy for Philip II of Spain who, rather than helping the Ottomans,
worked against them in the service of Spain. While the Jews’ complicated his-
tory with Spain—the expulsion of 1492 and the Inquisition’s relentless pursuit
of Jewish converts well into the seventeenth century—would seem to preclude
their participation in the Spanish spying network, Sacerdoti handily overcame
such hurdles. Using Sacerdoti as a test case, this article explores the boundaries

6 Nicolay, Nicolas de. Les Navigations, Peregrinations Et Voyages, Faicts En La Turquie, Par
Nicolas De Nicolay Daulphinoys, Seigneur D’Arfeville … Contenants Plusieurs Singularitez
Que L’autheur Y a Veu & Obserué … Auec Soixante Figures Au Naturel Tart D’hommes, Que De
Femmes Selon La Diuersité Des Nations .. (Antwerp, 1577) 130; Nabil I. Matar, Islam in Britain,
1558-1685 (Cambridge, 1998), 173.
7 Henry Blount, A Voyage Into the Levant (London, 1636), 115; Matar, Islam in Britain, 1559-
1685, 174.
8 1604-1657 Manasseh ben Israel and Lucien Wolf, Menasseh Ben Israel’s Mission to Oliver
Cromwell: Being a Reprint of the Pamphlets Published by Menasseh Ben Israel to Promote
the Re-Admission of the Jews to England, 1649-1656; (London, 1901), 81-90, http://archive.org/
details/cu31924028590028 Accessed on November 28, 2012.
9 Matar, Islam in Britain, 1558-1685, 174.

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322 cassen

of Jewish life in early modern political relations between Spain and the
Ottoman Empire: a milieu that was open on the one hand, but maintained
ideological, social, and economic limitations on the other hand. It examines
Sacerdoti’s place in a multicultural Mediterranean milieu, while also seeking
to understand whether and to what extent Sacerdoti’s Jewish identity may
have been a factor, either personally or in the eyes of others, in the successes
or failures of his various espionage endeavors. Furthermore by describing how
a Jew was able to forge relations across geographic, political, and religious bor-
ders and analyzing the connections that one needed to cultivate to reach the
upper echelons of Spain’s imperial administration, the article also sheds new
light on how early modern secret information networks functioned.

Spain’s Spying Operation

Sometimes called “the second oldest profession,” spying had existed since
antiquity, but it was only during the sixteenth century that European intel-
ligence services reached levels of competence and professionalism that turned
espionage into an essential tool of government.10 In Europe, England and
Spain had the best spying operations. Farther east, the Ottomans presided
over networks that stretched across the Mediterranean and the Middle East.
As Noel Malcolm writes in Agents of Empire: “This was a news-hungry world in
which information was power and where, precisely because much of the news
was inaccurate or fragmentary, with irregular time-lapses in its transmission,
it was vital to accumulate as many overlapping reports as possible in order
to sift out the truth, or something close to it.”11 Merchants, who could travel
more freely, emerged as frequent information gatherers, but corsairs, mission-
aries, and other travelers also took on those roles. Early on, these networks

10 For more on early modern intelligence services and people’s fascination with secrecy
at the time, see Paolo Preto, I Servizi segreti di Venezia. Saggi 499 (Milano, 1994); Carlos
Carnicer and Javier Marcos, Espias de Felipe II: Los servicios secretos del Imperio Español
(Madrid, 2005); Daniel Jütte, Das Zeitalter des Geheimnisses: Juden, Christen und die
Ökonomie des Geheimen (1400-1800) (Göttingen, 2011); William Eamon, The Professor of
Secrets: Mystery, Medicine, and Alchemy in Renaissance Italy (Washington, D.C., 2010).
The stereotype of the Jew as the bearer of secret knowledge also has a long history, see
for example Elisheva Carlebach, “Attribution of Secrecy and Perceptions of Jewry,” Jewish
Social Studies 2 (1996): 115-36; Garrett Mattingly, “The Reputation of Doctor De Puebla,”
The English Historical Review 55 (1940): 27-46; Daniel Jütte, “Trading in Secrets: Jews and
the Early Modern Quest for Clandestine Knowledge,” Isis 103 (2012): 668-86.
11 Malcolm, Agents of Empire, 37.

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Philip II of Spain and His Italian Jewish Spy 323

were far from professional, and it was “surprisingly difficult to determine at

what point an intelligence-gatherer turns into a spy.”12 But as in many areas of
government and diplomacy, the states of the Italian Peninsula led the way with
the creation of a professional diplomatic corps, and, specifically, the office of
resident ambassador. This added much needed structure to the emerging spy-
ing networks, for the task of the renaissance ambassador was twofold: negoti-
ate policy and provide his masters with sensitive information.13 As Michael
Levin writes: “Ever since the development of permanent embassies, states and
statesmen have understood that ambassadors act as political analysts, as well
as outright spies.”14
The institutionalization of early modern spying agencies happened organi-
cally in response to circumstances, but in Spain, King Philip II played such a
significant personal role in shaping it that he is sometimes given credit for cre-
ating the “modern” intelligence services.15 He understood and believed in the
power and effectiveness of secret information. He needed it to successfully run
his empire, and it came naturally to his suspicious temperament.16 “[Philip’s]
suspicion became almost pathological. It led him to deceive his ministers; for

12 Malcolm, Agents of Empire, 223.

13 Michael J. Levin, Agents of Empire: Spanish Ambassadors in Sixteenth-Century Italy
(Ithaca, 2005), 154-182; see also Garrett Mattingly, Renaissance Diplomacy (Boston, 1955)
125-140; Preto, I Servizi segreti di Venezia, 12-13, 100-107, 137, 454-491; Catherine Fletcher and
Jennifer Mara DeSilva, “Italian Ambassadorial Networks in Early Modern Europe—An
Introduction,” Journal of Early Modern History 14 (2010): 505-12.
14 Levin, Agents of Empire, 154.
15 Carnicer and Marcos, Espias de Felipe II: Los servicios secretos del Imperio español, 13-27.
By contrast in England, Sir Francis Walsingham ran Queen Elizabeth’s entire intelligence
network for her. Béatrice Pérez ed., Ambassadeurs, apprentis espions et maîtres complo-
teurs. Le système de renseignement de l’Espagne au temps modernes (Paris, 2010).
16 Although recently Henry Kamen has tried to paint a more positive picture of the king,
Philip’s reputation remains that of a fanatical, extremely detail-oriented and secretive
man. H. Kamen, Philip of Spain (New Haven, 1997), 317-321; H. G Koenigsberger, “The
Statecraft of Philip II,” European Studies Review 1 (1971): 1-21; Carnicer and Marcos, Espias
de Felipe II: Los servicios secretos del Imperio español, 59-69. See also Geoffrey Parker,
The Imprudent King: a new life of Philip II, (New Haven/London, 2014) which argues that
micromanagement was Philip’s Achilles’ heel. For example, the king was obsessed with
details about the “building of the Escorial, however trivial, whereas many documents on
issues of national security contain few signs of royal interest…. Everyone who has wielded
executive power can sympathize with this statement: in a time of crisis, solving minor
problems can provide short-term satisfaction, even relaxation…. But Córdoba, Silva and
the rest felt that Philip did not ‘relax’ by doing other things just ‘sometimes’: they com-
plained that he did so constantly, so that ‘relaxation’ became escapism.” (116). In the final

Journal of early modern history 21 (2017) 318-342

324 cassen

he assured them that he would never listen to slanders against them, yet he
encouraged their subordinates to spy and report on them.”17
At times his predilection for secrecy, which shrouded his true intentions
even to his closest collaborators, led to “administrative chaos.”18 But his sub-
ordinates and others who wished to serve him in Spain or abroad knew that
one sure way to please him was with classified information. He paid particular
attention to the selection of his ambassadors, for they ran his intelligence net-
work. Stationed across the empire, they were responsible for recruiting spies
and agents, evaluating potential agents’ trustworthiness, and relaying their
information to the King. Philip’s most trusted ambassador, Guzman de Silva,
was sent to Venice, a hotbed of espionage, with the following instructions: “To
know and understand through all possible ways, means and forms the news
available to you.”19
In spite of the growing importance of spying, few spies were professionally
trained. Most of the secret information that Spanish ambassadors had access
to came from what historians Carlos Carnicer and Javier Marcos called ad hoc
spies or correspondents: people who happened both to have information and
in touch with a Spanish official. They were often merchants who could travel
without arousing suspicions. The main difference was that correspondents
operated on a regular basis, while ad hoc spies provided one-time informa-
tion. Agents, however, were a wholly different matter. They came nearer to
being what we would consider career spies, and their tasks involved frequent
secret missions on behalf of the crown. Anyone—including renegades, prison-
ers, even Turks and Jews—could become an ad hoc spy or a correspondent,
but agents, as Philip explained to his ambassador to France in 1584, had to be
“personas de calidad”—quality people. This meant they had to be Spanish,
Christian, and, if possible, members of the high middle class.20 Such criteria,
added to the Jews’ reputations as “Barabases,” generally prevented Jews from
joining the ranks of Philip’s spying agents.21 Nonetheless some Jews tried; oth-
ers were even sought after for their access to information.

pages of his book, in a section entitled “Enter Dr. Freud,” Parker argues that Philip offers
a “striking example of the ‘obsessional’ or ‘obsessive-compulsive personality’.” (369-372).
17 H. G. Koenigsberger, “The Statecraft of Philip II,” European Studies Review 1 (1971): 1-21;
Carnicer and Marcos, Espias de Felipe II, 59-78.
18 Koenigsberger, “The Statecraft of Philip II,” 6.
19 Cited by Carnicer and Marcos, Espias de Felipe II, 146.
20 Ibid., 119-130 and 303-331; also Malcolm, Agents of Empire, 223-231; Arenal and Wiegers,
A Man of Three Worlds, 1-20.
21 On the Jews as secret conspirators, see Carlebach, “Attribution of Secrecy and Perceptions
of Jewry.”

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Philip II of Spain and His Italian Jewish Spy 325

Joseph Nasi, the heir of a famous converso family, who fled Europe and
became a counselor of the Ottoman Sultan, was in a favorable position to
obtain and transmit intelligence information. It was also said that Joseph
Nasi hated Spain. His vagrant life—his family’s expulsion from Spain in 1492,
the fear of the inquisition, his escapes from Portugal, Antwerp, and Venice—
and the losses that came with it had been caused by Spain’s anti-Jewish poli-
cies. Only after moving to the Ottoman Empire could he revert to practicing
Judaism openly and living a life uninhibited by the constant threats of the
Inquisition and Spanish i­ntolerance.22 From Istanbul, he headed a banking
company with positions across the Mediterranean, had connections with
Jewish communities everywhere, and direct access to Sultan Selim, whose trust
in him appeared unshakeable. When the grand vizier Sokullu Pasha said to the
Sultan that Jews ought not to occupy high governmental position, the Sultan
replied that Nasi had always been a good servant and that no one had bet-
ter information on Christian affairs.23 Nasi’s contemporary and at times rival,
David Passi, was a double agent. Originally from Portugal, Passi had become a
confidant of Sultan Murad III, Selim’s successor, but he simultaneously served
the king of Portugal. Both sides prized him for his knowledge of the others, yet
no one truly trusted him. As Lipomano, the Venetian bailo said: “This David, for
one truth tells a hundred lies; he would betray us if he could; he is agent of Don
Antonio of Portugal and in the confidence of the King of Spain; he is the warm
supporter of Venice and the trusted spy of the Sultan.”24

22 In fact, Nasi helped finance and engineer the Ottoman’s siege of Malta in 1565. Though
the siege ultimately failed, King Philip II of Spain, who was leading Europe’s battle against
the Turks, ordered him killed for it. Scholars believe Nasi inspired Marlowe’s Jew of Malta.
Cecil Roth, “Joseph Nasi, Duke of Naxos, and the Counts of Savoy,” The Jewish Quarterly
Review 57 (1967): 460-472; Rosenblath, “Joseph Nasi, Friend of Spain,” in Studies in Honor
of M.J. Bernardete; Essays in Hispanic and Sephardic Culture, ed. Izaak A. Langnas and
Barton Sholod (New York, 1965); A. Arce, “Espionaje y ultima aventura de Jose Nasi (1569-
1574),” Sefarad 13 (1973): 257-286; Matar, Islam in Britain, 1558-1685, 173-175. See also Cecil
Roth, The House of Nasi: The Duke of Naxos (Skokie, IL, 2002); Andrée Aelion Brooks, The
Woman Who Defied Kings: The Life and Times of Dona Gracia Nasi (St. Paul, MN, 2002).
23 Letter quoted by Gurkan, “Espionage in the 16th Century Mediterranean,” 378.
24 Quoted by Gurkan, “Espionage in the 16th Century Mediterranean,” 387. There is some
evidence to suggest that Nasi, too, was courted by Christian forces, including Spain, and
that he himself had made overtures in Spain’s direction, although the extent of Nasi’s role
as a “double agent” is disputed. Baron dismissed Nasi’s overtures to Spain as made up and
impulsive, Salo Wittmayer Baron, A Social and Religious History of the Jews, 2d ed., (New
York, 1952), XVIII, 92; Rosenblatt and Gurkan, on the other hand, see him as a shrewd
political operator who would not have had any compunctions about giving information

Journal of early modern history 21 (2017) 318-342

326 cassen

Italian Jews without access to power were in a different situation. They

understood the value of intelligence, but, for them, getting the attention of
relevant authorities represented a considerable challenge.25 In 1569, Joseph
Ottolengho, a Jew from Cremona in State of Milan, claimed in a letter to Philip II
to have a relative in a faraway country who knew the secret to transforming
iron into steel.26 Five months later, Ottolengho wrote with a different proposal,
offering a secret scheme to help the governor recover taxes.27 The king saw the
letters and asked the governor of Milan to investigate, but there was no follow-
up to either proposal.28 Whereas Ottolengho was apparently turned down,
Sacerdoti, a Jewish merchant from the small town of Alessandria in the State
of Milan, established himself as a trusted source of information.

Simon the Spy: Networks and Connections

The Sacerdoti family had Spanish roots and probably arrived in Italy
around the time of the expulsion of 1492. Settled in Alessandria, Vitale
Sacerdoti (Simon’s father) and his brother-in-law Abramo della Torre operated
a bank and became active in the wheat trade. Simon Sacerdoti (he bore his
father’s name, Vitale, as his middle name) was born in Alessandria probably
around the 1530s and lived there his entire life. During the 1540s, Milan came
under the direct rule of the Spanish Habsburgs. This transition, which would

to Spain if it served his interests: Rosenblath, “Joseph Nasi, Friend of Spain,” 257-286;
Gurkan, “Espionage in the 16th Century Mediterranean,” 383.
25 Daniel Jütte made the point that some Italian Jews viewed secret information as their
access to political power. Daniel Jütte, “Trading in Secrets.”
26 AGS, Secretarias Provinciales libro 1203, fols 119-121: “Il doctor Giosepho Ottolengho hebreo
tiene uno suo amico e parente in lontani paesi verso l’oriente qual ha un secreto con il quale
converte qualsivoglia ferro in azzaio.”
27 AGS, Secretarias Provinciales libro 1203, fols 217-219: “Per parte de Joseph Huottolengo … di
notificar nele mani del doctor Molina conservator del patrimonio de VMta … fisco di balore
de vente mille ducati.”
28 Ottolengho could be the rabbi and printer of Cremona whom Joseph ha-Kohen held
responsible for the Talmud burning in Cremona. In his chronicle, ha-Kohen included a
letter that he wrote to Ottolengho explaining that a scholar of his stature should have
known better than to associate himself with people of ill-repute who ended up caus-
ing the burning of the Talmud. Isaiah Sonne, Expurgation of Hebrew Books. The Works of
Jewish Scholars. A Contribution to the History of the Censorship of Hebrew Books in Italy in
the Sixteenth Century (New York, 1943); Roberto Bonfil, Rabbis and Jewish Communities in
Renaissance Italy, (London, 1993), 190; see also Joseph ­ha-Kohen, Sefer Emeq Ha-Bakha,
Karin Almbladh, ed. and trans. (Uppsala, 1981), 112.

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Philip II of Spain and His Italian Jewish Spy 327

eventually prove tragic for the Jews of Milan and end with their expulsion in
1597, seems to have happened rather seamlessly for the Sacerdoti family. In the
decades that followed Philip II’s takeover of the State of Milan, we can see the
Sacerdotis develop the family business, form alliances with Spanish authori-
ties and the Italian nobility, and even play a role as secular leaders for the Jews
of Milan.29
In addition to Vitale’s and later Simon’s sharp political acumen, two fac-
tors can help explain the Sacerdotis’ good fortunes. First, the wheat trade
was crucially important in the Italian states in those years—it was the basis
of people’s diets, but not enough could be produced on the Peninsula so
wheat imports were vital to the population.30 Second, Milan occupied a stra-
tegic position in the Spanish Empire as the gateway for troops to Central and
Northern Europe. As the Dutch revolt turned to open war in the late 1560s
and Milan occupied a central position on the “Spanish Road,” Milanese bank-
ers, including Jews, provided supplies to the troops.31 The Sacerdotis positioned
themselves at the center of such affairs: as early as 1548, the newly installed
Spanish governor, Fernando Gonzaga, took their side in the first conflict that
he was called to arbitrate when the Sacerdotis were accused of selling wheat
illegally and briefly imprisoned. In 1550 the governor repeatedly helped Vitale
Sacerdoti collect some outstanding debts.32 Vitale Sacerdoti also became an
advocate for the Jews of Milan, a role regularly held by early modern court

29 On the Sacerdoti family, see Renata Segre, Gli ebrei Lombardi nell’età spagnola, vol. 28,
Memorie dell’Academia delle scienze di Torino 4, Turin,1973, 24-28; on the expulsion
from Milan, see Flora Cassen, “The Last Spanish Expulsion in Europe: Milan 1565-1597,”
AJS Review 38 (2014): 59-88.
30 Malcolm, Agents of Empire, 43-45: Venice, for example, needed 108 tons of grain a day, less
than half of which could be supplied by its Terraferma. The Republic strictly regulated the
grain trade as a result.
31 Geoffrey Parker, The Army of Flanders and the Spanish Road, 1567-1659 (Cambridge, 1972);
on the centrality of Alessandria in the transalpine route for Spanish troops, see G. Tonelli,
Affari e lussuosa sobrietà. Traffici e stili di vita dei negozianti milanesi nel XVII secolo (1600-
1659), (Milano, 2012), 28. For more on Spanish troops in Milan, see A. Dattero, Soldati a
Milano. Organizzazione militare e società lombarda nella prima dominazione austriaca
(Milano, 2014); D. Maffi, Il baluardo della Corona. Guerra, esercito, finanze e società nella
Lombardia seicentesca (1630-1660), (Firenze, 2007); on the strategic place of Milan for
Philip II and the role of Jews therein, Cassen, “The Last Spanish Expulsion,” 63-68.
32 Segre, Gli ebrei Lombardi nell’età spagnola, 24; Shlomo Simonsohn, The Jews in the Duchy
of Milan. A Documentary history of the Jews of Italy (Jerusalem, 1982), 1128, 1133, 1153, 1168,
1175.

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328 cassen

Jews. But by becoming active in the trade of information, Simon took the fam-
ily’s service to the Spanish crown to a different level.
Simon Sacerdoti was not an official agent, however he came as close as a Jew
could to being gainfully employed as a spy by the Spanish king. According to
the archives of the Spanish Chancellery in Milan, between 1560 and 1584 ten
payments were made out to Simon Sacerdoti for journeys and secret missions
accomplished for the king of Spain. In 1560 he was paid eight scudi for a trip
to Germany and Zurich. In 1562 again he took a trip to Zurich on the king’s
account, for which he was paid 20 scudi, and in 1568 he was paid 150 gold scudi
for carrying out a commissione secreta. He accomplished another secret mis-
sion in 1569, for which again he received 150 gold scudi. In 1570 he traveled to
Piedmont and was paid 20 scudi. In 1576 he was paid 200 scudi for expenses
incurred on several secret missions on behalf of the governor, the Duke of
Albuquerque. In 1580 he was paid another 60 scudi for missions accomplished
on behalf of the king, and in 1584 he was paid a total of 65 scudi for the same.33
The documents preserved in the archives of Milan record only the pay-
ments. For information on what he actually did, one needs to read the cor-
respondence between the king of Spain and the Spanish governor of Milan,
and between the king and his ambassadors in various Italian states. These men
competed to send the most valuable intelligence to their king, and their let-
ters, containing confidential and sensitive information, were handled with
great care. The secret parts were encoded (each Spanish ambassador had his
own cipher, which was changed periodically), and they were preserved in the
archives of Simancas, a fortress located near the town of Valladolid in Spain,
built by Philip II for the purpose of keeping his archives.34
The clearest demonstration of Simon’s importance and effectiveness as a
spy comes from four documents written in 1585, 1591, and 1592. In those reports
Philip’s counselors verified Simon’s service to the crown to help the king decide
whether and how much to pay him. The four reports concur that he helped
foil French plans to take Alessandria and Savona, provided information about
a projected Spanish mutiny, discovered several Turkish spies in Milan, and
undertook a number of missions to Constantinople, Germany, and Provence

33 Simonsohn, The Jews in the Duchy of Milan, 1367-68.

34 For tables with the codes of all the ambassadors, see Jean-Pierre Devos, Les chiffres de
Philip II (1555-1598 et du despacho universal durant le XVII e siècle (Bruxelles, 1950); for
more on how the codes were constructed, see: Jeffrey Adler, Ryan Fuoss, Michael Levin,
Amanda Yuell, “Reading Encrypted Diplomatic Correspondence: an Undergraduate
Research Project,” Cryptologia 32 (2008): 1-12.

Journal of early modern history 21 (2017) 318-342

Philip II of Spain and His Italian Jewish Spy 329

upon orders from the governor and “for secret things of great importance.” And
as the governor of Milan added: “he has always been engaged in commissions
and affairs involving secrecy and trust.”35
Unlike Ottolengho, Sacerdoti understood that writing to the king was not
enough; one also needed to gain the trust of Spanish officials. The family
had relations with the governor, but ambassadors were the ones in charge of
the king’s espionage networks, and Spanish administrators often competed
rather than cooperated.36 To reach into the information networks, Sacerdoti
secured referrals from two sources close to the king: Don Martin de la Nuca,
an Aragonese nobleman who was a close friend of Antonio Perez, Philip II’s
secretary; and Emmanuel Philibert, Duke of Savoy and Philip’s first cousin.
Emmanuel Philibert had served as his governor in the Netherlands from 1553
to 1559, just when Joseph Nasi, fleeing the Portuguese Inquisition, settled in
its commercial capital, Antwerp. There, Nasi and the future Duke of Savoy
appear to have become acquainted. In a letter that he asked Simon Sacerdoti to
deliver to Nasi in person, Emmanuel Philibert wrote: “The friendship which
was so long since contracted between us when we were both in the Low
Countries.” Clarifying Simon’s role in the relation, he added later in the letter:
“For this reason, I have decided to send to your illustrious Lordship Simone di
Sacerdote, a Jew who, as I understand from the good report that he had often
brought to me of your generous nature (confirming even further what I already
knew) is as devoted a servant to you as he is to me.”37 Spanish diplomatic

35 AGS, Secretarias Provinciales, 1796 # 33: “siempre ha sido occupado en comissiones y nego-
cios de secreto y confianca.” And AGS, Secretarias Provinciales 1795 # 333: “descubriendo
tratados e inteligencias de francese y muchas espias motines en Alexandria el Castillo de
Milan y Saona y endo cinco vezes a Levante y otras muchas a Alemana, Provenca y otras
partes con orden delos governadores de aquel estado y por cosas secretas y de grande impor-
tancia.” See also AGS, Secretarias Provinciales 1794 # 323 and 1221 # 227-9.
36 For more on the ambassadors, see Levin, Agents of Empire. On Spain’s imperial admin-
istration, Pedro Cardim et al., eds., Polycentric Monarchies: How Did Early Modern Spain
and Portugal Achieve and Maintain a Global Hegemony? (Eastbourne, UK/Portland, OR,
2012); Antonio Alvarez-Ossorio Alvariño, Milan y el legado de Felipe II: Gobernadores y
corte provincial en la Lombardia de los Austrias (Madrid, 2001); Antonio Alvarez-Ossorio
Alvariño, “The State of Milan and the Spanish Monarchy,” in Spain in Italy: Politics, Society,
and Religion 1500-1700, ed. Thomas James Dandelet and John A. Marino (Leiden, 2007),
99-135; and Claudio Donati, “The Profession of Arms and the Nobility in Spanish Italy,” in
Spain in Italy: Politics, 299-325.
37 Cecil Roth, “Joseph Nasi, Duke of Naxos, and the Counts of Savoy,” The Jewish Quarterly
Review 57 (1967): 469-470.

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330 cassen

correspondence further reveals that Emmanuel Philibert recommended

Simon to Philip II’s ambassadors, his spymasters.
In a letter dated July 1567, Don Martin de la Nuca described how Simon
Sacerdoti had approached him to offer valuable intelligence.38 This letter also
divulges who Simon’s contacts were and how he made his case for being a spy.
When Simon approached Don Martin, he had just returned from a mission to
Jerusalem on the orders of the Duke of Albuquerque, governor of Milan. While
there, Simon told Don Martin, he established friendships with a number of
important Jews who had contacts in Istanbul. He was also a close friend of a
factor of Joseph Nasi (Juan Michas in the letter). Though this in itself would
be an important source of intelligence on the Ottoman Empire, Simon added
that his father was close to Nasi, too, though he was now too old to undertake
the journey to Istanbul himself. Both letters suggest that Simon was closely
connected to Nasi’s network, through which he gained ears in the highest
spheres of Ottoman power. He was offering such access to the Spanish king
precisely when tensions were running high between the two empires in the
Mediterranean.39 A close look at two of Sacerdoti’s secret missions illustrates
how valuable his information potentially was.

Two Secret Missions: Buggia and Savona

One such secret strategic affair was a plan to take Buggia, a fortified city on the
Barbary Coast of North Africa, called Bejaia in modern-day Algeria. Spain had
occupied Buggia from 1510 to 1555 when it lost it to the Ottomans. Retaking it
would have represented an important victory, and Simon’s timing was judi-
cious in this regard. He approached the Duke of Savoy about a year before
the battle of Lepanto, a time when anxiety over Turkish domination of the
Mediterranean Sea was particularly high and the Spanish navy was preparing
for a major confrontation against the Ottomans. It probably helped that Philip
had already heard of Simon Sacerdoti through Martin de la Nuca, for shortly
after Simon proposed his plan, correspondence on Buggia started flowing
between Philip II and his ambassadors. On January 1, 1570, Guzman de Silva,
the Spanish ambassador in Genoa, wrote Philip that he received a letter from
the Duke of Savoy concerning some matters dealt with by Sacerdoti and that,
upon recommendation of the Duke, he sent him on a mission. It is not clear
what this mission entailed, but it seemed quite important and timely to the

38 AGS, Estado 1222 # 49.

39 AGS, Estado 1222 # 49.

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Philip II of Spain and His Italian Jewish Spy 331

ambassador and the Duke because they dispatched Simon even before know-
ing Philip’s opinion on the matter.40 On April 25th, a new letter from Guzman
de Silva reported on the mission. In it we learn that the Duke of Savoy had
sent Simon Sacerdoti to Argel, currently El Jazair in Algeria, where he gath-
ered information on Buggia. Simon, the Duke reported, had a friend in Nice, a
sailor called Geronymo Nicardo, who told him that it should be quite easy to
take Buggia because the city was badly guarded by only fifty elderly janissar-
ies. Simon’s plan was a classic Trojan-horse strategy: he would visit the Caliph
whom he knew well, carrying large gifts, which would require him to enter the
city with a few men. Once inside, they would kill the caliph and send a signal to
the soldiers left in the boats to storm the city.41 He then added that once Buggia
was taken, Argel could be taken as well, but that Argel could not be taken
without Buggia.
On May 2nd, Guzman de Silva wrote another letter to the king after having
received more information from Simon. He started by telling the king that he
thinks that the idea is worth pursuing because “this man is known, has much
experience with these matters and has also opened a line of communication
with a Castilian in Buggia.”42 He then reiterated Sacerdoti’s assurances that the
city could be taken with relatively few soldiers and few weapons because arms
and munitions would be waiting for them there. Anticipating the king’s next
question, he specified that he asked Simon to clarify who were the people who
would bring the weapons to Marseille, Argel, and other places, information
that Sacerdoti could not reveal. All he could say was that these would-be revo-
lutionaries were smugglers who carried weapons in barrels of wine fitted with
an internal compartment that concealed weapons while keeping them sepa-
rate from the wine. The lead, Sacerdoti explained, came directly from England
and was hidden under the ballast of ships originating there. Interestingly,
Sacerdoti added that this was also how heretical books were smuggled out
of England and into Spanish lands.43 Evidently the plan had been thought

40 AGS, Estado, 1399 # 8: “Anoche tuve carta del Duque de Saboya cuya copi embio a VM … me
ha parecido despachar este hebreo conforme a lo que el Duque escrive por no aver tiempo de
saber lo que VM sera servido quese haga en ello y ser necessaria la brevedad.”
41 AGS, Estado 1399 # 42: “… va a visitar el califa, que es muy su conocido, y les llevara un pre-
sente y con esta occasion podrà meterse en el castillo … podrian matar al califa.”
42 AGS, Estado 1399 # 43: Y ame inclinado a juzgar que puede tener algun fundamento este
trato por ser aquel hombre conocido y que tiene mucha experiencia delo ally y particular
communicacion con castellano que esta en Bugia.”
43 AGS, Estado 1399 # 43.

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332 cassen

through in detail, and the ambassador felt it was worth pursuing, but what was
the king’s opinion?
On June 4th, the king’s reply arrived. He was interested in the plan writing
that if it was indeed that easy, they may soon have the opportunity to try it.44
Meanwhile, he instructed Guzman to collect as much information as possible
pertaining to the plan and report back to him.45 Philip was a cautious mon-
arch who did not take military decisions lightly, and yet his interest in the plan
was undeniable. June 1571 was five months before the battle of Lepanto; he was
already busy planning war in the Mediterranean. The fact that Sacerdoti was
Jewish did not seem to have bothered him; he did not even comment on it. His
only concern was the quality of the information. On September 23, 1571, Philip II
asked Guzman to encourage Sacerdoti to proceed with the plan, and even to
grant him a safe-conduct to come and explain his plan at the Spanish court.46
Five years after threatening to expel the Jews from Milan, Philip II was invit-
ing one of those Jews to his court.47 Yet nothing came of that visit because the
news that followed was bad. A day before Philip sent his September 23rd letter,
Guzman had learned of a serious problem: “The Jew who dealt with the matter of
Buggia” had been caught by the governor of Marseille and apparently confessed
to the plan. The ambassador did not hide his disappointment: “he tenido pena”—
I was sad—he wrote, revealing that he had believed strongly enough in the
plan to develop an emotional stake in it.48 Two days later, on October 20,
Guzman de Silva sent the king a new letter saying that, in fact, Sacerdoti had
not been taken. He had met him together with the Duke of Savoy and, once
more, felt much hope for their project.49 He added that the Duke suggested
sending a ­soldier dressed as a sailor to inspect the place.50 The circumstances

44 AGS, Estado 1400 # 81: “Que si ello ha de tan fácil como ello, haze poco se aventurara en
provarlos.”
45 AGS, Estado 1400 # 81: “Entre tanto podreis vos yros informando del todo lo que del se pudi-
erre saber y avisarnos dello.”
46 AGS, Estado 1400 # 88.
47 This echoes the situation in which his father found himself having to borrow from New
Christian bankers in Naples in order to finance his campaign in N. Africa while being
committed to expel them from his dominions. See Peter Mazur, The New Christians of
Spanish Naples, 1528-1671: a fragile elite, (London, 2013) 81-99.
48 AGS, Estado 1399 # 98: “que al hebreo que trato delo de Bugia avia prendido el governador de
Marsella y avia descubierto el negocio que el avia escrito sobre ello al duque de Saboya.”
49 A GS, Estado 1399 # 99: “El Duque y este hebreo estan tan confiados que me hazen tener mas
esperanca.”
50 AGS, Estado 1399 # 99: “para ver la disposicion de aquel lugar, vestido como un hombre del
navio para que como confidente y platico queda dar buena razon de todo.”

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Philip II of Spain and His Italian Jewish Spy 333

of Sacerdoti’s capture and release were not satisfactorily explained, which

seems to have tamped down the king’s enthusiasm for the plan. He responded
two months later, on December 26, 1570, only acknowledging receipt of the
ambassador’s letter.51 The plan indeed seemed shady now. Having just won an
impressive victory at Lepanto, Philip may not have attached the same value to
Buggia as before.52 In addition, perhaps the mere threat of Sacerdoti’s divulg-
ing sensitive information to local authorities sobered Philip by reminding him
of possible unintended consequences.
Meanwhile a French plan to take Savona was quickly moving forward.
Within a few days the Spanish ambassadors in Genoa and Turin informed the
king of it. On November 5, 1571, Juan de Vargas Mexia, Spain’s ambassador in
Savoy, wrote that “the Jew who dealt with the Buggia affair” had given him infor-
mation on a French plan to take the fort of Savona. Mexia describes himself as
having taken a tough stance with Sacerdoti, telling him that if his information
were solid he would be compensated, but that he should not dare to fool him.
Sacerdoti replied that everything he said was true and that Mexia could put
him in jail while he verified his assertions.53 That being said, Mexia went on to
explain the French plan, which involved poisoning Spanish soldiers’ wine. The
poison would either kill them all within seven hours or put them to sleep for
twenty-four hours. French soldiers waiting outside would then scale the wall
with ladders and storm the castle. Four days later, the ambassador in Genoa
reported the same information.54
Although Sacerdoti was quite active and appeared in numerous letters in
1570-71, he temporarily disappeared from the record in 1572 and 73. When he
reappeared in 1574, it was again to help Spain capture Buggia. Just as it had
two years earlier, the plan involved an elaborate Trojan-horse strategy using
merchant boats to hide soldiers. Sacerdoti had a friend with access to corre-
spondence between the King of France and one of his secretaries, and in those
letters the two discussed how easy it would be to take Buggia because the city
was badly guarded. To take the city before the French, Sacerdoti offered to use

51 AGS, Estado 1400 # 91: “He holgado de entender la buena esperanca que tiene el hebreo que
trata de lo de Bugia y de que el duque de Saboya quisiesse embiar persona platica para ver el
sitio de aquel lugar para que tanto mejor se vealo que convenga.”
52 Andrew Hess, “The Battle of Lepanto and Its Place in Mediterranean History,” Past and
Present 57 (1972): 53-73; Malcolm, Agents of Empire, 162-172.
53 AGS, Estado 1230 # 161: “Yo le replica que y affirmando me lo le dize que si era cosa de funda-
mento y no vanidad lo tratasse conmigo que le gratificaria y saria gratificado pero que no me
diesse palabras certificamelo tanto diziendo que se ponia en prision hasta verificar lo.”
54 AGS, Estado 1230 # 161.

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334 cassen

one of his large merchant ships to carry out the attack. His plan was to travel
there with four or five merchant ships in which 150 to 200 soldiers could hide.55
Philip was still interested in capturing Buggia and asked Ayamonte to dis-
cuss it with his brother, Don Juan de Austria (naval commander of the Spanish
fleet at Lepanto). But on Sacerdoti, Philip had made his own inquiry and came
to different conclusions: “On this Vidal who has proposed this plan; here he
is not thought to be a man of much standing or seriousness and it is under-
stood that very little will come out of this.”56 Had the earlier Buggia fiasco
tarnished Sacerdoti’s reputation? Or was there another reason for the king’s
skepticism? Sacerdoti was, after all, a man of many worlds, whose complex alle-
giances to Philip II, his governor and ambassadors, Duke Emmanuel Philibert,
Joseph Nasi, and Milan’s Jews were bound to create conflicts of interests. What
was Sacerdoti doing in 1572 and 1573, when he was absent from Spanish and
Italian diplomatic correspondence?

Simon Sacerdoti Thwarts His Spanish Masters

As we have seen, Emmanuel Philibert, Duke of Savoy from 1559 to 1580, was
close to Philip II. As first cousins they had grown up together at the court of
Charles V, and Philibert had served as Philip’s governor in the Netherlands
from 1550 to 1559. There he became acquainted with Joseph Nasi.57 Still, this
friendship did not predispose Philibert well towards all the Jews. A year after
taking the reins of the Duchy of Savoy, Philibert resolved to expel them.58

55 AGS, Estado 1239 # 12.

56 AGS, Estado 1239 # 192: “Aunque aquel Vidal que os ha propuesto esta platica no se tiene aca
por hombre de mucho fundamento y assi se entiende que se podria hacer muy poco desta.”
(Vidal was the Spanish rendering of Simon’s middle name—Vitale.).
57 See the Duke’s letter to Nasi which starts: “The friendship which so long since was con-
tracted between us when we were both in the Low Countries” Roth, “Joseph Nasi, Duke of
Naxos, and the Counts of Savoy,” 11.
58 This experience was traumatic for the Jews. Joseph ha-Kohen, the famous doctor, histo-
rian and chronicler of Italian Jewish life in the sixteenth century, recounted it thus: “Also
Filiberto Emmanuel, the Duke of Savoy, wanted to expel the Jews from all the lands of
Piedmont. The Jews were very frightened and threw themselves at his feet and before
Margaret, his wife and the sister of King Henri, and brought her a gift. On that day, she
accepted them and talked to their hearts, and their stay was extended by four months. But
Negron de Negri the Genoese, a base man, a thorn in their side agitated the Duke against
them, who then said: ‘Leave my land; be out in six days!’ The Jews trembled in fear and
cried out to the Lord who sent them a certain physician who was residing at the Duke’s

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Philip II of Spain and His Italian Jewish Spy 335

Five years later, the Duke of Savoy again expelled the Jews. But a month after
the Jews’ departure, he changed his mind and readmitted them for ten years
for a payment of 3000 scudi “to please persons in our special favor.”59
After this, the Duke reversed his attitude toward Jews. He resolved to bring
more Jews to his lands. Between 1569 and 1570 he opened the doors of his
Duchy to expellees from the Papal States, and in 1572, he issued a privilege
granting trading and banking rights and protection from inquisitorial pro-
ceedings to all Jews, including Spanish and Portuguese Marranos. His goal was
to attract wealthy Jews from Spain and Portugal, as well as Jewish merchants
from Constantinople, and to create a trading hub in Villefranche near Nice.
Those who convinced him to embark on this project were none other than
Vitale and Simon Sacerdoti, both named in the first sentence of the privilege.60
Additionally, the Duke sent Simon to Constantinople with a letter to his friend
Joseph Nasi, to ensure that the Jews who settled in Villefranche would have
advantageous trading relations with Turkey.61 The letter reveals Emmanuel
Philibert’s ambition to lead trade with the Levant:

My present desire is to obtain a safe-conduct for some of my vassals

and subjects from Villefranche and Nice and other places subject to me,
to go freely into the dominions of the said Grand Signor on barks and
other vessels only to trade and carry on their business-in the same way

court. He spoke positively about them to the Duke, who made a covenant with them.
And they have been living there to this day.” Joseph ha-Kohen, “Emek ha-Bakha,” Shene
Sefarim Niftahim: Korot U-tela’ot ‘am Yisra’el Be-artsot, Ephraim ben Jacob ed. (Jerusalem,
1971) 165.
59 Segre, The Jews in Piedmont, 447-453. Joseph ha-Cohen recorded the 1565 expulsion too
but got a number of the facts wrong. He dated it to 1566, called the Duke Joseph Filibert
instead of Emmanuel Philibert, and wrote that the Duke “who was greedy” ordered the
Jews to pay 4,000 golden coins or leave his lands. The Jews left but few days later, they
came back with 2,000 golden coins, after which the duke readmitted them and granted
them a new condotta, or “covenant” with a yearly tax of 1,500 golden coins. Joseph ha-
Kohen, “Emek ha-Bakha,” 170. Apparently when not in Milan or Genoa, places Joseph was
intimately familiar with, the level of accuracy of Emek ha-Bakha decreases.
60 “Havendoci humilmente supplicato Vital di Sacerdote, et Simone suo figliuolo, di voler con-
ceder privileggi concessioni immunita a tutta la natione Hebrea di qual grado et conditi-
one … che possano venir star et habitar … et viver conforme alle loro leggi,” published by M.
Lattes, “Documents et notices sur l’histoire des juifs en Italie,” Revue des études juives 5
(1882): 232-233. Haim Beinart, “Settlement of the Jews in the Duchy of Savoie in the wake
of the Privilege of 1572,” in Scritti in Memoria di Leone Carpi, ed. Attilio Milano, Alexander
Rofe, and Daniel Carpi (Jerusalem/Milan, 1967), 72-118.
61 Roth, “Joseph Nasi, Duke of Naxos, and the Counts of Savoy,” 469-470.

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336 cassen

as I have granted a safe-conduct for Turks, Armenians, Persians, Indians

and Levantines to come to my States and ports as they please to trade and
conduct their business. In order that the said commerce may be carried
on more conveniently and safely, I hope that the said Grand Signor will
let these subjects of mine have a consul for the affairs that arise daily,
whether in Alexandria or in Tripoli of Syria. I opine that this will be
granted all the more readily since it will benefit the customs and import-
dues, and will be useful moreover to his vassals and subjects in disposing
of their wares and merchandise.62

Although the privilege was nominally applicable to people from all countries,
it was also an invitation to Spanish and Portuguese Jewish converts to move to
Savoy and enjoy protection from inquisitorial proceedings.63
Emmanuel Philibert realized that Spain would disapprove of his policy, but
he underestimated the strong resistance Spanish forces in Milan and Madrid
would deploy against him. It started on the day that he issued his privilege,
September 4, 1572. Juan de Vargas Mexia, the Spanish ambassador in Turin,
sent a letter to Antonio Perez, Philip’s secretary in Madrid, informing him of a
rumor that “a certain rich Jew from Milan” (Vitale or Simon Sacerdoti) had made
plans to come and live in Villefranche, along with wealthy Muslim and Jewish
converts.64 Mexia’s letter was followed by an intense correspondence between
Turin, Milan and Madrid on how to deal with this problem.65 (Fig. 1) This went

62 Ibid., 469.
63 “[E]t viver conforme alle loro leggi, con prohibitione espressa che contra di lor non si possi
da inquisitore or altra persona ecclesiastica in tempo alcuno essercitare ne intentare veruna
sorte d’inquisitione, visitatione, denuntiatione, accusatione et esecutione in esser chiamati
ne citati in giuditio per causa di apostasia oo sia appocrisia, o per qualonche altro delitto
di qual sorte si vogli, concernente materia di fede …” published by M. Lattes, “Documents
et notices sur l’histoire des juifs en Italie,” Revue des études juives 5 (1882): 232-233. Haim
Beinart, “Settlement of the Jews in the Duchy of Savoie in the wake of the Privilege of
1572,” in Scritti in Memoria di Leone Carpi, 72-118. This document was not preserved in the
archives of Piedmont-Savoy, which may reveal the care and secrecy with which the Duke
surrounded this project. Lattes found a copy in the archives of the Jewish community of
Padua, and Beinart located another copy in Simancas, Philip II’s archive in Spain.
64 Beinart, “Settlement of the Jews in the Duchy of Savoie in the wake of the Privilege of
1572,” 86: “Entre otras chimeras que andan entablando voy rastreando una que trata cierto
judio rico del estado de Milan para venirse a vivir a este con algunos otros y que tiene cor-
respondencia para el mismo effecto con particulares conversos moros y judios dessos reynos
y en especial de Portugal. De los quales van viniendo segun me dizen personas ricas y traen
consigo lo que tienen.”
65 The entire correspondence was published by Beinart, ibid., 72-119.

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Philip II of Spain and His Italian Jewish Spy 337

figure 1 A page out of a report by ambassador Juan de Vargas Mexia on the “trade” mission
to Constantinople that Simon (not named here) accomplished for the Duke of Savoy.
A sensitive passage was encoded. After the letter reached Philip’s administration in
Madrid, the letter was decoded in the left margin and above the text.

Journal of early modern history 21 (2017) 318-342

338 cassen

on until Philip II brought the matter to the Pope, and in May 1573, Emmanuel
Philibert expelled Spanish and Portuguese Jews from his territories.66
This may explain Philip’s reluctance when Simon Sacerdoti tried once again
to sell his Buggia plan in 1574. The man who had consorted with Joseph Nasi
and conspired with him and Emmanuel Philibert to help conversos out of
Spain was not to be trusted. With the free port at Villefranche, Sacerdoti put
the interests of his own religious community before those of Spain.67 And yet,
his fall from favor was only temporary. By 1576, he was on a secret mission again
for the Spanish governor of Milan; he was paid for at least two more secret mis-
sions in 1580 and 1584; in 1591 he obtained a safe conduct to travel to Spain; and
in 1599 he and his family were the only Jews permitted to remain in the Duchy
of Milan. All the others had been expelled and forced to leave; Sacerdoti was
granted this exceptional favor in recognition of his services to the crown.68

Back to Serving Spain?

Given the failure of Simon’s plan to take Buggia and the debacle at Villefranche,
both of which tarnished his reputation at the Spanish court, it is remarkable
that Philip allowed only Simon Sacerdoti, a Jew who had disappointed if not
betrayed him, to stay in Milan with his family. Sacerdoti’s access to secret infor-
mation probably justified keeping him on hand, despite Philip’s misgivings.

66 Segre, The Jews in Piedmont, 55; Beinart, “Settlement of the Jews in the Duchy of Savoie in
the wake of the Privilege of 1572,” 72-85.
67 Other examples of Italian free ports were Ancona and later Trieste. Port cities and free
ports allowed for the appearance of “port Jews” starting in the middle of the sixteenth
century; for more see David Cesarani, ed., Port Jews: Jewish Communities in Cosmopolitan
Maritime Trading Centers, 1550-1950 (London/New York, 2014), 1-12 and 47-74; Lois Dubin,
The Port Jews of Habsburg Trieste: Absolutist Politics and Enlightenment Culture (Stanford,
2011); and the recent Francesca Bregoli, Mediterranean Enlightenment: Livornese Jews,
Tuscan Culture, and Eighteenth-Century Reform (Stanford, 2014).
68 After the expulsion of the Jews from Milan, the king allowed four representatives (Simon
Sacerdoti, Celemente Pavia, Isach Suavi, Conseglio Carmini) to stay in order to help settle
the Jews’ outstanding debts and businesses. In 1599, only Simone Sacerdoti obtained the
right to continue to reside in Alessandria from the Spanish governor: Archivio di Stato
di Milano, Cancelleria Spagnola, Carteggio Generale, cart 350, fasc. 2. See also Cassen,
“The Last Spanish Expulsion in Europe,” 84. In the middle of the seventeenth century and
again in 1686, the bishop of Alessandria and the Pope petitioned the governor to expel the
Jews. Both reports mention that only Simon Sacerdoti and his descendants had received
permission to stay in Milan, from the king in 1491, which was later reconfirmed by several
governors. Simonsohn, The Jews in the Duchy of Milan, 2124-2126, 2162-2164.

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Philip II of Spain and His Italian Jewish Spy 339

Both the Duke and the governor had reasons to seek independence from the
Spanish monarchy. Savoy was a small Duchy “sandwiched” between France
and Spanish Italy and struggling to gain autonomy from both. The governors
were close collaborators of the king; men he entrusted with considerable
power and responsibility, and he expected them to act as his representatives
abroad. But the Spanish Empire’s vastness made gubernatorial independence
almost inevitable.69 The trend increased toward the end of Philip’s reign, when
illness incapacitated him, and governors were torn between their loyalty to
him and their own desire for more power. Under such circumstances, a supply
of good information became even more critical.
Thus the Duke of Savoy and the governor of Milan continued to support and
employ Sacerdoti despite the king’s increasingly negative assessment, and they
were instrumental in helping to rebuild his reputation as a servant of Spain.
On the eve of the expulsion, when the time came to examine Sacerdoti’s record,
the governor vouched for him, enumerating the missions he accomplished in
Spain’s name. Sacerdoti was granted a lifelong pension in addition to the right
to reside in Milan after the expulsion of the Jews.70
But perhaps the most intriguing aspect of Sacerdoti’s story relates to his
actions in Madrid where he went to advocate against the expulsion of the Jews
from Milan. Joseph ha-Kohen writes about him in glowing terms and praises
him for getting all the way into the king’s palace to forcefully make the case of
the Jews:

There was a Jew in Alessandria by the name of Samuel [Simon] ha-

Kohen. He offered to go to Spain on behalf of the Jews to plead for his
fatherland.… [A]fter he arrived in Spain, he conferred with the councilors
about the plight of the Jews. He even succeeded in getting all the way into
the palace where the King and his highest ministers were. He spoke in
the name of the Jews and asked why he planned to deal in this way with
his servants who had assisted him and his father in times of trial. He said
that they were still ready today to help him with as much and more for
the poor and indigent in case this became necessary, and that they could
bring witnesses to justify them. But if the king had once decided to expel

69 John Elliott, “A Europe of Composite Monarchies,” Past and Present 137 (1992): 48-71;
Guiseppe de Luca, “Trading Money and Empire Building in Spanish Milan (1570-
1640),” Polycentric Monarchies, 18-125; Alberto Marcos Martin, “Polycentric Monarchies:
Understanding the Grand Multinational Organizations of the Early Modern Period,”
Polycentric Monarchies, 217-226.
70 AGS, Secretarias Provinciales 1796-35, 36, 37, 38.

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340 cassen

them, he would then demand, in the name of the Jews, that he first repays
them what they could rightfully claim; for this is what justice demanded.71

Yet if instead of Jewish records one turns to Spanish archival documenta-

tion, it appears that Simon spent much of his time in Madrid trying to secure
his pension and his own family’s future in Milan.72 We do not know what
Sacerdoti’s intentions were. He may have reasoned that reminding the king of
his lengthy service would save all the Jews from expulsion. Likewise, we don’t
know whether Milan’s Jews were aware that Sacerdoti had advocated primar-
ily for himself and his family in Madrid. This was another moment of possible
dissonance between Sacerdoti’s multiple roles, in this case his interests as a
well-connected political operative in the Mediterranean versus his individual
or communal identity as a Milanese Jew. However, neither at the time of the
expulsion, nor during the events at Villefranche some twenty years earlier,
did the Spanish monarch allow Jewish individual or collective interests to rise
above his own. That the Jews’ efforts emanated from a known collaborator
and that their impact on Spanish fortunes would have been minimal, if at all,
made no difference.

Conclusion

Simon Sacerdoti was an unusual character, and through his story, this
article has sought to explore the tensions between communal identities
and ­transnational relations, and to shed new light on the place of Jews in
Spain’s intelligence ­networks in the sixteenth century. The early modern
Mediterranean was a context in which identities, as scholars have long argued,
were “fluid and protean.”73 However, intelligence networks, upon which mili-
tary victory and national security depended, were by necessity more guarded.
Communications were coded; the trustworthiness of sources was thoroughly
checked, and the veracity and usefulness of information needed to be con-
firmed and reconfirmed multiple times. Only a skillful political operator
capable of cultivating relations with Spanish governors and ambassadors,
Italian noblemen, and Ottoman officials (through Nasi’s network) could
penetrate such formidable barriers. Philip needed good intelligence on the
Turks, and he relied on having trustworthy spies everywhere; Simon Sacerdoti

71 Ha-Kohen, Sefer Emeq Ha-Bakha, 112-13. The name Samuel should be Simon, as attested in
numerous Spanish documents in the archives of Simancas.
72 AGS, Secretarias Provinciales 1796-35, 36, 37, 38.
73 Dursteler, Venetians in Constantinople, 1-20.

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Philip II of Spain and His Italian Jewish Spy 341

understood this and acted accordingly. A product of the Mediterranean of his

time, he dealt quietly and effectively with cultural and religious differences,
competing interests, and overlapping allegiances.
Along with Sacerdoti’s intellectual and political intelligence, one must also
consider the Jews’ situation at that time. Expulsions and resettlements in new
lands, conversions to Christianity and back to Judaism (often by way of crypto-
Judaism) shaped their experience.74 If one looks at Sacerdoti in the context of
Spain’s attitudes to Jews in those years—continued support for the Inquisition
and the impending expulsion of the Jews from Milan—his actions, especially
at the time of the expulsion, may raise questions of loyalty to the Jewish com-
munity. Likewise, given the history of Spain’s treatment of Jews and the prev-
alence of stereotypes of Jews as Ottoman spies, Spanish officials’ continued
employment of Sacerdoti and their trust in him is surprising too. However,
when taking into account the totality of Sacerdoti’s actions what stands out is
his adaptability. As Jews have done fairly consistently in the different diaspora
settings that they lived in, Sacerdoti faithfully served his king through his gov-
ernors and ambassadors.75 But his attempt to create a free port in Villefranche
represents a moment where his concerns for converted Jews seeking to flee
Iberia superseded his service to the king. Similarly when traveling to Madrid
to advocate against the expulsion of the Jews from Milan, he appears torn
between his community’s interests and his own position as a Spanish operator
in Milan. This suggests that a connected environment is not one where ten-
sions between communal or individual identities and transnational relations
dissolved, but rather a dynamic space in which individuals from a variety of
backgrounds can find a place despite persisting tensions.76 Thus, unmoored

74 David Ruderman argued that “mobility” was one of the defining features of early modern
Jewry: David B. Ruderman, Early Modern Jewry: A New Cultural History (Princeton, N.J./
Woodstock, 2011).
75 His attitude could be seen as standard application of the Talmudic maxim “dina de-­
malkhutei dina,” by which Jews accepted the law of the land provided it did not conflict
with the Torah. Gil Graff, Separation of Church and State: Dina de-Malkhuta Dina in Jewish
Law (Tuscaloosa, AL., 2003), 8-29.
76 Indeed Linda Darling sees “transformations in the Islamic world as similar to those in
Western Europe, generating an image of two civilizations on parallel rather than oppos-
ing tracks.” In Linda Darling, “Rethinking Europe and the Islamic World in the Age of
Exploration,” Journal of Early Modern History 2 (1998): 221. More broadly, Trivellato argues
that the early modern era was characterized by the cross-cultural interactions of indi-
viduals from different geographic, political, linguistic, and religious backgrounds, even
though such identities could be rigidly defined and controlled. Trivellato, The Familiarity
of Strangers, 271-278.

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342 cassen

and versatile as they were, early modern Mediterranean Jews had adapted
quite well to a fluctuating Mediterranean world.
Indeed, the story and career of Simon Sacerdoti challenge our picture of
what was possible for Jews in early modern Spain. Sacerdoti was an Italian Jew
with connections in Istanbul who became a subject of the Spanish empire as
a result of European dynastic wars. Jews did not have the right to reside in the
empire of Philip II of Spain, and if a person was suspected of being Jewish, his
or her life was in danger. Yet Sacerdoti became a spy for Philip II. He transmit-
ted information and ideas to Philip who listened and took him seriously. When
the opportunity arose to establish a trading hub in Savoy that would welcome
Spanish and Portuguese conversos seeking to flee the inquisition, he did so
even though it threatened to undermine his standing with Philip. But the rela-
tionship recovered, and a few years later Sacerdoti was again lending his ser-
vices to the king. He carried on until Philip’s death and was richly rewarded: he
and his family were allowed to remain in their hometown of Alessandria in the
state of Milan, while all other Milanese Jews were forced to go. The boundaries
for the Jews of that period were real and difficult to navigate, but Sacerdoti’s
life is an illustration of how porous they could be.

Journal of early modern history 21 (2017) 318-342