POLITHE A53

TOLISORA, Alexandra Christine, V., 12032069

April 21, 2023

The art of statecraft: A book analysis on Niccolo Machiavelli’s The Prince

The Prince remains relevant despite being written in a context-specific timeline: the time
of political turmoil during the Italian renaissance. Applying the Machiavellian prince to Philippine
politics, cacique rulers satisfy the minimum criteria. Under this political system, cacique rulers or
bosses are coercive and monopolistic over territorial resources, which makes their politics
personalistic as Machiavelli’s state (Anderson 1988; Machiavelli 2014; Sidel 1997). Considering
that they satisfy the personalistic aspect of Machiavelli’s state, it is worth exploring: To what
extent were cacique rulers in the Philippines Machiavellian? By reading the Prince and
analyzing cacique politics using Sidel’s (1997) study on Cavite & Cebu bossism, I contend that
the extent to which they are Machiavellian depends on their statecraft skills. Essentially, cacique
rulers exercise power differently. Hence, calling the need for further elaboration of how certain
bosses ruled in their respective states.
Bearing in mind that cacique rulers vary in their leadership style, this paper will first
elaborate on two of the provinces that experienced cacique democracy. Specifically, Cavite and
Cebu. Through this, I shall introduce the context by which these provinces are akin to a
Machiavellian state, and how these provinces are similar to the concept of a civil state. Then, I
will be proceeding to analyze the 2 successful cases of bossism—particularly, Ramon Durano
Sr. & Isidro Escario’s leaderships and how their strategies had proven Machiavelli’s (2014)
treatise to be effective. Then finally, to 2 failed cases of bossism—particularly, Cesar Casal and
Sergio Osmena Jr.’s leaderships and how the warnings of Machiavelli (2014) in his treatise led
to the collapse of their leaderships.

Bosses, and the states in which they ruled

Local cities, Cavite and Cebu, are akin to Machiavelli’s state – wherein they are
personalistic, and are monopolistic towards resources. The term “state” relies heavily on the
prince’s status. It is a personal possession (Borja 2023). Comparing Machiavelli’s (2014) state
to Charles Tilly and Max Weber’s, all three are similar in a sense that they are mostly concerned
with the ruler’s power—the power of the ruler to undertake wars & extract resources from his
constituents to continue fighting wars, and the power of the ruler to monopolize the use of
legitimate violence (Tilly 2010; Weber 1946). In terms of the kind of state Cebu and Cavite
bosses ran, they were civil states. Civil states are states where rulers are chosen by their elites
and citizens through elections. In here, the challenge is to please both his citizens and the
nobles while also fending off possible political threats that might lead to his losing the state.
Examining the cases of Cebu and Cavite, civil states are run differently—which will be
elaborated below. After elaborating the nature of Cebu and Cavite states, this chapter will
discuss Machiavelli’s (2014) take on the organization of the states.
Bosses in Cebu relied heavily on the elites through clientelistic relationships to win
government seats (Sidel 1997). They are also reliant on proprietary power, and business
wealth—which they use to monopolize agricultural job opportunities, and other business
sectors. With that said, Cebu bossism extracts power from networks and legal businesses. It
engages less in illegal economic activities to maintain political power. On the other hand, the
civil state in Cavite is more unstable. Firstly, bosses could not proprietary wealth for themselves
because land is under the control of the government (Sidel 1997). Secondly, Cavite was heavily
reliant on violence—with a record of “twenty-one Cavite municipalities having a mayor that was
murdered or accused of murdered” (Sidel 2018). As such, Cavite under such bosses was
dangerous to live in.
Machiavelli (2014) wrote advice for civil states like Cavite and Cebu. In terms of his
advice on a Cebu-like civil state, such a civil state favored by the elites is the second most
preferred principality. This is due to the fact that he believes that the masses could overthrow
the prince if they are not satisfied with his ruling. Whereas, if elites aren’t but the majority
supports him, they would have little incentive to have a boss killed. But as per the account of
Sidel (1997) on Cebu bossism, bosses encountered little to no opposition from the masses.
Hence, it can be said that even if Cebu bosses mostly relied on elite alliances, the masses did
not despise the bosses at the time of their leadership. In terms of Machiavelli’s (2014) advice on
a Cavite-like civil state, a civil state heavily reliant on violence is dangerous. To him, over relying
on violent strategies is dangerous. He does not suggest it because this may lead to a ruler
being despised, causing his people to overthrow him in the future. Furthermore, he is also
cautious of wealth being reliant on government power. As per Machiavelli (2014), rulers who
acquire power using the fortune of others would have no trouble gaining power but would be
having troubles maintaining power. Hence, if proprietary power, through the fortune of others
(the government) could not be retained through reelections, Cavite bosses’ properties would be
passed onto the hands of others.
Overall, Cavite and Cebu are similar to Machiavelli’s state because their politics are
personalistic, and they are territories within countries. In terms of the kind of state Cavite and
Cebu bosses had, they were civil states. Wherein, local elites and masses vote for rulers
through elections. But the nature in which these civil states were operated by bosses were
different. In Cebu, political power was reliant on elite alliances. With which, Machiavelli (2014) is
considered as the second most preferable state, preferring a ruler whose support mostly comes
from the masses. In Cavite, political power was reliant on violence, and proprietary wealth can
only be achieved by winning the elections. With which, Machiavelli (2014) was wary because
wealth depended on the fortune of a government seat, and power was heavily reliant on
violence.

Failed cases of bossism: Sergio Osmena, Jr. in Cebu, and Cesar Casal in Cavite
The Roman virtu means to be a man of flexible qualities (Borja 2023; Machiavelli 2014).
Virtu can be closely associated with prowess— “...courage and skill to impose one’s will on the
world” (Unger 2011). Virtu determines if a ruler shall withstand fortuna; uncontrollable
circumstances that can affect one’s situation. In the case of Sergio Osmena, Jr. in Cebu, and
Cesar Casal in Cavite, their virtu, and foresight for political threats, were not enough to survive
fortuna. Casal’s strategy was to rely heavily on violence to win the elections, and government
power to attain proprietary wealth, confirming that Cavite politics is more unstable than Cebu
politics. On the other hand, Osmena Jr., while not relying on government positions for power,
over relied on benevolence in staying in power but failed to consider that meanness may be
necessary towards opponents. Hence, leading to Casal and Sergio Osmena, Jr.’s loss of
political power. In narrating the cases of the said politicians, this chapter will determine what
was the advice of Machiavelli against the virtu these bosses showed during their tenure.
Cesar Casal from Cavite campaigned using political networks and electoral violence
(Sidel 1997). He won as the mayor of Carmona and ruled from 1955 - 1979. During his rule, he
acquired more than three hundred hectares of communal lands in Carmona through
intimidation, and provided many farmers jobs so Casal could control the agrarian economy.
Indeed, he gained proprietary wealth through his mayoral powers. But after losing the elections
after 1979, since it is public property, the government had taken the acquired lands from Casal –
failing to pass the properties to his family members. In this case, Machiavelli (2014)’s story of
how Duke Valentino lost his territories when his father, Pope Alexander VI, died is quite similar
with Casal’s property losses. Previously warning that acquiring power through the fortune of
others is easy to attain but hard to maintain without appropriate statecraft skills and/or
connections, their properties were taken after the Duke’s father’s papal power was gone, and
after Casal lost the 1980 elections.
 On the other hand, Sergio Osmena, Jr. was already wealthy before he entered politics
(Sidel 1997). As a mayor of Cebu city, he maintained a local political machinery through the
constant provision of government contracts. However, the problem of Sergio Osmena, Jr. was
not maintaining supporters. But rather, angering a more powerful politician, former President
Ferdinand Marcos Sr., when he ran against him in 1969. Although Marcos, Sr. won at that time,
he did not stop tarnishing the reputation of Sergio Osmena, Jr. by accusing him of playing a role
in the plot to slaughter him (Saxon 1984). Additionally, Marcos Sr. also took extra steps to
overpower the clan by taking over the Osmena allies’ government contracts – transferring the
wealth of the latter’s supporters to Marcos Sr.’s instead. The story of Sergio Osmena, Jr. is
similar to that of Machiavelli (2014)’s case of Clodius Albinus – who, after attempting to murder
Septimius Severus – had angered the latter, and fought each other until Albinus’ had killed
himself because his soldiers are losing against Severus’. In this case, what Machiavelli (2014)
was trying to say is that: it is not suggested to earn the anger of enemies who they could not
defeat. Oftentimes, their retaliation could heavily affect a ruler’s political power – with Sergio
Osmena, Jr. losing his government contracts, and Albinus losing his war against Severus.
In conclusion, Cesar Casal and Sergio Osmena, Jr. had failed to maintain political power
for numerous reasons. In the case of Casal, he was not reelected during the 1980 elections –
leading to the loss of his three hundred land hectares which are considered as government
properties. Whereas, Sergio Osmena, Jr. has failed to maintain political power not because of
the lack of support or wealth in Cebu, but rather by angering a more powerful politician, former
President Marcos Sr. All in all, lessons drawn from these failed cases of bossism politics are that
a ruler: (a) must choose his enemies wisely, (b) must learn how to foresee potential problems
like election losses, and (c) must depend less on the fortunes of others.

Successful cases of bossism: Ramon Durano, Sr. and Isidro Escario

As opposed to Cesar Casal and Sergio Osmena, Jr., Ramon Durano, Sr. and Isidro
Escario of Cebu showed moral flexibility—allowing them to adapt to unpredictable
circumstances like elections and market competitions. By being morally flexible, Ramon Durano
Sr., and Isidro Escario were able to appear generous to their supporters, but also capable of
inflicting injury to their enemies. Essentially, they used both coercive measures during and after
elections. Considering that the two bosses used various strategies of coercion and generosity,
this chapter will expound on what were the steps taken by them in ensuring the longevity of their
power. Furthermore, analysis will be drawn on how such strategies led to their success using
the advice of Machiavelli (2014).
 One boss that successfully consolidated power was the late Ramon Durano Sr. Durano
Sr. came into politics around the 1940s and continued serving various positions in the
government until the 1990s (Sidel 1997). [For the purpose of this case analysis, I shall only
focus on his 1949 congressional position]. His methods were a mixture of appearing liberal and
being cunning during and after elections. During the 1949 elections, he was able to win as a
congressman of Cebu by accumulating powerful elite supporters, while also engaging in
electoral violence like fraud to intimidate voters. During his rule, he regularly ensured that his
allies were awarded government contracts and loans in certain businesses (ex. mining) and
lands. This, in return, deprived his enemies of market opportunities; allowing the Durano
supporters and the family to monopolize the majority of the businesses in Danao, Cebu (the
hometown of the Durano family) and to prevent competition. Outside of ensuring that his
political machine is intact and enemies are overpowered, he aimed to extend political support to
the masses by building infrastructures concerning public health; such as a hospital, the Ramon
M. Durano Sr. Foundation Inc. Memorial Park, factories, and elderly homes (Associated Press
News 1988). In doing so, Durano, Sr. avoided the risk of being despised by his people and
being defeated by his enemies. He knew when to be cruel, and when to be giving.
Another boss who exemplified outstanding moral flexibility is Isidro Escario (Sidel 1997).
Prior to being elected, he was a tax clerk. Government work allowed him to gain the support of
prominent politicians who were willing to endorse him for the 1937 elections, while using
coercive methods to make non-supporters vote for him simultaneously. After winning as a mayor
of Bantayan, Isidro’s tactics to stay in power were also a combination of generosity and
meanness; which helped him rule until 1964. In terms of meanness, he established his private
armies by controlling the police force, selectively enforcing laws on the businesses of
explosives, & fishing only to those that they do not want to engage in businesses with, and
monopolizing the employment of migrant farmers in sugar plantations. In terms of generosity,
since the clan holds a monopoly over many industries, the Escarios became important patrons
for Cebuanos’ that are seeking job opportunities under the businesses they handle. As such,
much like Durano Sr., Escario carefully chooses which people he shall be cunning and
generous to. He aims to injure his competitors by depriving them of business opportunities,
while providing benefits to his political machinery.
Overall, Durano, Sr. and Escario were successful in maintaining power because of their
moral flexibility. Instead of relying on either kindness or cruelty to consolidate power, they had
done what Machiavelli (2014) advised: that is, to be able to appear generous and cruel
whenever necessary. “Whenever necessary” has no definite criteria. However, analyzing the two
cases of Durano, Sr., and Escario, appearing liberal is necessary towards supporters, and the
masses. In doing so, it painted the bosses as generous patrons–providing them security, and
other benefits. In terms of being cruel, it is only necessary if there are competitors that can
possibly challenge a boss’ leadership. For example, Durano, Sr. and Escario are mostly
coercive towards opposition voters during elections. And after elections, they are cruel in such a
way that they monopolize numerous business sectors and prevent competitors from joining the
market.

Concluding remarks
Machiavelli’s treatise is relevant in understanding up to what extent were cacique rulers
in the Philippines Machiavellian. Analyzing bossism politics in Cavite and Cebu, this paper
discovered that cacique rulers exercise power differently. There are bosses that display the
qualities of a Machiavellian prince, and there are bosses that do not display such qualities, [only
the desire to rule and to monopolize resources]. By “qualities of a Machiavellian prince,” this
means the show of moral flexibility, and foresight for potential conflicts. As analyzed by this
paper, bosses who showed Machiavellian qualities were Ramon Durano, Sr. and Isidro Escario;
while those that failed to show Machiavellian qualities were Cesar Casal and Sergio Osmena,
Jr.
Recalling why Ramon Durano, Sr. and Isidro Escario were successful, this is because
they exhibited moral flexibility, and were able to foresee political conflicts that could undermine
their authorities. These are qualities that go beyond the minimum criteria of Machiavelli’s prince
and his personalistic state. Hence, they are the ideal princes. Both Durano, Sr. and Escario
knew when to appear generous, and when to be cruel. They had not overtly relied on either
cruelty or kindness only to prolong their ruling. There are instances in which they are generous
[to their allies], and cunning [to their enemies]. Furthermore, such moral flexibility was also
maintained throughout their leadership – during the elections, and even after they were elected
into office. During their elections, both bosses expanded their political machinery, while resulting
in electoral violence like fraud and intimidation to persuade the opposition to vote for them. After
being elected, both bosses ensured that their allies had access to government contracts and
created business monopolies – which prevented non-supporters from competing with them. In
exhibiting consistent moral flexibility, Durano Sr. and Escario were loved and feared – appearing
as kind and giving to their supporters, while intimidating their enemies.
On the other hand, Sergio Osmena, Jr. and Cesar Casal failed to prolong their power
due to the inability to withstand fortuna. Sergio Osmena Jr. failed not because of a lack of
political network, but because he ran against a [more] powerful enemy, former President
Ferdinand Marcos Sr. during the 1969 presidential elections. With Osmena Jr. losing the
elections, Marcos Sr. had ensured that once sworn into office, Osmena Jr. and his allies would
lose their political power with Marcos Sr. taking the Osmena family and allies’ government
contracts – which were awarded to his cronies instead. Drawing comparisons between the
Osmenas and Machiavelli’s The Prince (2014), the Osmena, Jr.’s case is much like Claudius
Albinus; who angered Septimius Severus when the former attempted to kill him – leading to a
war with which Severus emerged victorious. Similarly, Casal failed to prolong his power and lost
his properties because he was not reelected during the 1980 local elections. In failing to be
reelected, not only did he lose political power, but also proprietary power since lands are under
government control. Therefore, the lands could not be controlled if Casal was not an officer.
Similarly with Machiavelli’s (2014) account of Duke Valentino losing his territories, both of their
powers relied heavily on the fortunes of others. To Duke Valentino, he owes his territories to his
late father, Pope Alexander VI. Whereas, Casal owes his lands to his mayoral position.
All in all, this paper showed that Machiavelli’s (2014) treatise foresees political conflicts
that can cause the collapse of a ruler, as well as qualities that may prolong one’s leadership.
Indeed, The Prince had been helpful in analyzing what were the strengths and weaknesses of
cacique bosses. In terms of bosses’ strengths, successful bosses Ramon Durano, Sr. and Isidro
Escario proved the essence of balancing meanness and generosity. In terms of bosses’
weaknesses, failed bosses Cesar Casal and Sergio Osmena, Jr. highlighted Machiavelli’s
(2014) warnings against the acquisition of power through the hands of others (the government,
in Casal’s case), and competing against a politician that amassed more power.
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