He played college football for the Mary Hardin-Baylor Crusaders and was signed as an undrafted free agent by the Tennessee Titans of the NFL in 2008.

Freeman played four seasons of collegiate football for the Mary Hardin-Baylor Crusaders under Pete Fredenburg.

[14] In Week 1 against the Chicago Bears, Freeman returned a Jay Cutler interception for a touchdown in the first quarter.

[17] Freeman won the AFC Defensive Player of the Week award for his performance in a 23–7 win over the Kansas City Chiefs on December 22, 2013.

[24] In the 2015 season, he finished with three sacks, 112 total tackles, one interception, two passes defended, and one fumble recovery in 13 games and starts.

[28] On September 12, 2017, Freeman was placed on injured reserve after sustaining a pectoral injury and a concussion in Week 1 against the Atlanta Falcons.

[29] On October 30, the Chicago Bears announced that Freeman had been suspended for 10 games for violating the NFL's performance-enhancing drug policy for a second time.

[30] Freeman apologized for the suspension, adding that his playing career might be in jeopardy due to a head injury and memory loss.