Caldwell played college football for the Florida Gators, where he was a member of a BCS National Championship team.

A third-round pick in the 2008 NFL draft, he played professionally for the Cincinnati Bengals and Denver Broncos.

[3] His senior year, he moved from wide receiver to starting quarterback, and passed and rushed for over 2,220 yards and thirty-eight touchdowns while leading the Dragons to a Florida Class 4A state championship game appearance.

[3] He was the Tampa Tribune's Hillsborough County Player of the Year, an all-state selection, and was named a Parade magazine, SuperPrep and USA Today high school All-American following his senior season in 2002.

[5] As a Florida collegiate, he joined the Gators track & field team following the conclusion of spring football practice.

[8] During his sophomore season in 2004, Caldwell's production jumped to forty-three catches and three receiving touchdowns, as well as two rushes for sixty-six yards and one score.

[9] He received a medical redshirt for the 2005 season after fracturing his leg in an early-season Southeastern Conference (SEC) game against the Tennessee Volunteers.

[16] As a senior team captain in 2007, Caldwell recorded a career-high 761 yards and seven touchdowns on fifty-six receptions, had twelve carries for fifty-eight rushing yards and a touchdown, and was the recipient of the Gators' Fergie Ferguson Award as the "senior football player who displays outstanding leadership, character and courage.

"[17][18] Caldwell finished his senior season with 100-yard receiving games against the Western Kentucky Hilltoppers, Vanderbilt Commodores, South Carolina Gamecocks, and Florida Atlantic Owls.

[1] In his rookie year, he made contributions in late season as a receiver and kickoff returner, and finished with eleven receptions for seventy-eight yards, a 26-yard average on thirteen kickoff returns, and five rushes for fifty-three yards during his rookie season.