Dooley's political career began with part-time positions in the village of Northwoods, where he and his family reside.

Dooley won the election defeating the Republican nominee, former County Executive Gene McNary.

In 2006, Dooley was reelected to a full term as County Executive, defeating the Republican nominee, Joe Passanise, by gaining 67% of the vote.

In a difficult mid-term election season for Democrats, Dooley was elected to serve a second full term as County Executive in 2010, defeating the Republican nominee, Bill Corrigan, 51.1% to 46.7%, with the Libertarian candidate receiving 2.2% of the vote.

[1] On August 5, 2014, Dooley lost his bid to be the Democratic Party candidate in the County Executive election to primary challenger Steve Stenger.