He won the Democratic primary, and faced Anna Cowin, a Lake County School Board Member and the Republican nominee.

Dean campaigned on his law-and-order credentials and experience as sheriff, sharply criticizing Cowin's plan to eliminate parole and probation altogether, arguing, "You can't sit someone in a cell doing hard time forever.

The bitterly fought campaign, however, left feelings of antipathy between the two candidates, with Dean later remarking, "Anna Cowin won our election.

When Argenziano, whom Dean had succeeded in the House, was appointed to the Florida Public Service Commission by then-Governor Charlie Crist, a special election was held to fill the vacancy in the 3rd District, which stretched from Tallahassee to the Jacksonville suburbs, Ocala, and Citrus County.

Dean ran to succeed her, and faced fellow State Representative Dennis K. Baxley and Don Curtis in the Republican primary.

[12] Dean ended up narrowly defeating his opponents, receiving 45% of the vote to Baxley's 44% and Curtis's 11%, and advanced to the general election, where he faced Suzan Franks, the Democratic nominee.

During the campaign, Franks attacked Dean for voting for a massive property tax cut, which she argued would bankrupt local government agencies.