He then received his Juris Doctor from Columbia Law School in 2005, and moved back to Florida, where he was a losing contest on Season 5 of The Apprentice.

After leaving the show, Díaz began working for Akerman LLP as an attorney specializing in commercial litigation and zoning and land use.

In 2010, when incumbent State Representative Juan-Carlos Planas was unable to seek re-election, Díaz ran to succeed him in the 115th district, which narrowly stretched from Doral to Cutler Ridge in Miami-Dade County.

Neither of his opponents proved to be a significant obstacle, however, and Díaz easily defeated both of them in a landslide, winning 64% of the vote to Solomon's 33% and Blau's 3%.

He faced fellow State Representative Ana Rivas Logan in the Republican primary, and an extremely contentious election ensued.