Roosevelt attended St. Joseph's Collegiate Institute in Buffalo where he played at the quarterback position before staying in Buffalo to attend the University at Buffalo. Roosevelt was the first recruit of new head coach Turner Gill. He started seven games as a freshman and was converted into a wide receiver, catching 31 passes and 2 touchdowns. In his second year, the wide receiver caught 63 passes and 4 touchdowns. In his junior season, Roosevelt dramatically increased his production, catching 104 passes, primarily from quarterback Drew Willy. On September 13, 2008 Roosevelt caught a Hail Mary pass from QB Drew Willy as time expired against the Temple Owls. Also in his junior season, Buffalo won the 2008 MAC Championship Game against Nate Davis and the Ball State Cardinals. Roosevelt's 104 receptions was one short of the MAC Conference record at the time. Roosevelt graduated in 2009 and, the following season, Roosevelt caught 70 passes and 9 touchdowns.
Professional career
NFL
Roosevelt went undrafted in the 2010 NFL Draft. He was signed as an undrafted free agent by the Buffalo Bills on April 24. Roosevelt was cut by the Bills on final cuts on September 4, 2010, but signed to their practice squad on September 5, 2010. On November 27, 2010, Roosevelt was promoted from the practice squad to the active roster. On October 16, 2011, Roosevelt caught his first pro TD pass, a 60-yard catch-and-run at MetLife Stadium against the New York Giants. On August 31, 2012, he was cut by the Bills. On July 23, 2013, he was signed by the Cleveland Browns. After the 2013 season, he was not re-signed and was signed after a tryout for the Detroit Lions on April 23, 2014. After being let go by the Lions, he signed with the Buffalo Bills on July 21, 2014. The Bills released Roosevelt on August 29, 2014. On October 3, 2014 the Bills re-signed Roosevelt to the practice squad. He was released from the practice squad on October 4, 2014.
Saskatchewan Roughriders
Roosevelt signed with the Saskatchewan Roughriders of the Canadian Football League on March 14, 2015. Roosevelt had a breakout year for the Roughriders in his second season in the CFL. He played in the first 11 games of the season before being placed on the six-game injured list. Following the season he was named the Riders Most Outstanding Player despite missing 7 games. Additionally, he accepted a two-year contract extension from the Riders. Roosevelt finished the 2016 season with 1,095 receiving yards, the ninth-highest total in the league. 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. At the time of the injury Roosevelt was the Riders leading receiver, and had the fifth most receiving yards in the league with 923. Roosevelt was named a divisional All-Star for 2017 after another 1,000 yard season and 8 touchdown catches, but had a down year in 2018 with injuries to both himself, as well as several injuries to new starting quarterback Zach Collaros. 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, and Duron Carter. 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 $160,000 Canadian Dollars, as well as performance incentives to increase earnings. Roosevelt rewarded the Riders with a bounce-back year; he played his first season of all 18 games, and despite only one touchdown catch, he caught 77 passes for 946 yards, with which Roosevelt surpassed the 4,000 yard mark for his career, as well as making his 300th catch. Following the season he was not re-signed by the Riders and became a free agent on February 11, 2020.
Montreal Alouettes
On February 22, 2020 Roosevelt signed with the Montreal Alouettes.
