In 2016, Legg returned to the University of South Florida to earn a Doctorate of Education (EdD) in Program Development and Innovation.

[2] In 1998, Legg began working for State Representative Heather Fiorentino as her staff director, a position he would hold until 2001.

In 2002, Republican State Representative Mike Fasano was unable to seek re-election due to term limits.

[4] Legg ended up winning the nomination, receiving 54% of the vote to Stewart's 46%,[5] and advanced to the general election, where he faced Dee Thomas, a physical therapist and the Democratic nominee.

In 2008, he faced Ron Rice, a land surveyor for the city of Clearwater and the Democratic nominee, and John Ubele, a member of a white nationalist organization and an independent candidate.

Given that legislators are required to live in the districts they represent, Rice noted, "It seems to me as if Mr. Legg is having a difficult time choosing between his family and his political career.

He was initially planning on running in the 18th District, and would have faced wealthy egg farmer Wilton Simpson in the primary.

[12] The Tampa Bay Times endorsed Legg, citing his "ability to develop a consensus" to address problems, though noting that he shaped education policy, "both good and bad," pushing "controversial bills.