Whouley is President of the Dewey Square Group, a consulting firm that works for both political and corporate clients as lobbyists and campaign strategists.
Whouley, who spent his childhood and launched his career in the Dorchester section of Boston, Massachusetts,[1][2] was a key strategist for Bill Clinton, serving as his field director during the 1992 election.
Following Clinton's inauguration, Whouley became a lobbyist on behalf of pro-North American Free Trade Agreement (NAFTA) interests.
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.
Mark Halperin of Time reported on December 14, 2007, that Michael Whouley had been working for Senator Hillary Clinton's Iowa campaign for several weeks.