Whouley was a key strategist for both Al Gore in 2000 and John Kerry in 2004. Whouley helped jumpstart both Gore's and Kerry's comeback in the presidential primaries after they came close to being overtaken by Bill Bradley and Howard Dean respectively.
Whouley is regarded as one of the Democratic Party's best field strategists and as a result has earned the nickname "The Wizard". Despite this, he is fairly reclusive and very rarely does media interviews. He avoids reporters as much as possible.