During his playing career, he was a member of the Buffalo Bills, Cleveland Browns, Detroit Lions, Saskatchewan Roughriders, Montreal Alouettes, and Winnipeg Blue Bombers.

Roosevelt said that outlook changed when he was recruited to attend St. Joseph's Collegiate Institute, a private school in suburban Tonawanda.

As a senior in 2005, he threw a Western New York record 35 touchdown passes and was named the Buffalo News' Player of the Year.

[7] Roosevelt was converted to wide receiver as a freshman and started seven games, catching 31 passes and 2 touchdowns.

[9] On September 13, 2008, Roosevelt caught a Hail Mary pass from quarterback Drew Willy as time expired to beat the Temple Owls at UB Stadium.

Also in his junior season, Buffalo won the 2008 MAC Championship Game against Nate Davis and the Ball State Cardinals.

[15] On November 27, 2010, Roosevelt was promoted to the active roster after coach Chan Gailey said he did an "excellent job" on the practice squad.

[17][18] On December 19, 2010, he was targeted with and caught the first passes of his NFL career,[17] reeling in two of three throws from Ryan Fitzpatrick for 35 yards.

Bills General Manager Buddy Nix said of the move "This year, we cut guys that were good players.

[21] On October 16, 2011, Roosevelt caught his first pro touchdown pass, a 60-yard catch-and-run at MetLife Stadium against the New York Giants.

[30] In Week 14 of the 2017 season Roosevelt took a helmet-to-helmet hit from Calgary's Tunde Adeleke and was placed on the team's six-game injured list.

[32] The Roughriders offense had already taken hits prior to and during the regular season with the release of experienced pass catchers such as Rob Bagg, Chad Owens, Bakari Grant,[33] and Duron Carter.

[34] Several days into free agency for 2019, Roosevelt turned down an offer from rival Winnipeg to sign a one-year extension with the Roughriders for roughly Can$160,000, as well as performance incentives to increase earnings.

[41] On February 2, 2024, it was announced that Roosevelt had joined the Hamilton Tiger-Cats of the CFL to serve as the team's receivers coach.