He played college football for the Kansas State Wildcats, and was selected by the Tampa Bay Buccaneers in the first round of the 2009 NFL draft.

Freeman became the starter for Tampa Bay in his rookie year and went on to break numerous franchise passing records.

Freeman was also a member of the Minnesota Vikings, New York Giants, Miami Dolphins and Indianapolis Colts, as well as the Montreal Alouettes of the Canadian Football League (CFL) and the Brooklyn Bolts of the Fall Experimental Football League (FXFL).

[1][2] As a sophomore, he threw for 1,946 yards and 24 passing touchdowns, leading Grandview to a 9–3 record and a spot in the quarterfinals of the Class 4 playoffs.

As a senior, he was the #4 pro-style rated quarterback in the country by Rivals.com as well as being ranked as the #92 overall prospect in the nation by Rivals and the top player in the state of Missouri.

He led Grandview to a 7–4 record, a district title and a berth in the sectional round of the Missouri state playoffs.

[5] Despite being a highly recruited quarterback prospect, one major program wanted the 6' 5" 225 lb Freeman as a tight end, which his African-American father saw as a racial slight.

He replaced Dylan Meier at quarterback during the second half at Baylor and directed the Kansas State offense the rest of the season.

Additionally, he had consecutive 250+ yard passing games against Colorado and Texas, marking the first time a Kansas State quarterback had done so since Michael Bishop in 1998.

He accumulated a school-record 8,427 total yards and joined Ell Roberson as the only quarterbacks in Kansas State history to score at least 60 touchdowns.

On December 27, 2009, he led the Buccaneers to a 20–17 overtime win over the 13–1 New Orleans Saints, preventing them from clinching the top seed in the playoffs for one more week.

[27] On January 1, 2011, Freeman completed 21 of 26 pass attempts for 255 yards and two touchdowns against the playoff-bound New Orleans Saints.

[34][35] The Buccaneers also added new weapons for Freeman, signing former Indianapolis Colts tight end Dallas Clark, Pro Bowl wide receiver Vincent Jackson, and upgrading the offensive line with All-Pro left guard Carl Nicks.

Freeman steadily improved in 2012, throwing 11 more touchdowns, five fewer interceptions, and 500 more passing yards compared to the 2011 season.

[37] After a poor performance in a 23–3 Week 3 loss to the New England Patriots, Freeman was benched in favor of rookie quarterback Mike Glennon.

[38][39] The Buccaneers began the season with a disappointing 0–3 record, and Freeman was completing 46% of his passes with a near league bottom 59.3 rating (30th).

[52] Freeman played in Miami's preseason finale against his former team, the Tampa Bay Buccaneers on September 3, 2015.

[55] In his first game with the Bolts, which took place during typhoons created by the oncoming Hurricane Joaquin, Freeman fumbled five times in the wet conditions, losing three of them, and threw an interception.

[57] He started the final game of the regular season against the Tennessee Titans on January 3, 2016, due to injuries to starter Andrew Luck and reserve Matt Hasselbeck.