Wynn attended Ginn Academy in the Glenville area of Cleveland, Ohio, where he was teammates with Ohio StatequarterbackCardale Jones. He played wide receiver and also returned kicks and punts. As a senior, he was all-district selection and named third team All-Ohio. In addition to football, Wynn was a stand-out track athlete, winning Ohio state title in 2009 and 2010 in the 4 × 200 m relay and the 4x400 indoor relay. Considered a three-star recruit by all major rating services, Wynn was ranked as the No. 62 wide receiver nationally in 2011. He chose Indiana over Penn State and Toledo on National Signing Day.
College career
Freshman year
As a freshman, Wynn lead the Hoosiers with 1,249 all-purpose yards. Most of his production was on kick returns, as he returned 48 kicks for 1,015 yards and a touchdown. His kick return and all-purpose yardage totals were Indiana true freshman records. He was named Big Ten Freshman of the Week after returning the opening kickoff for a 99-yard touchdown against Illinois.
Sophomore year
In 2012, Wynn received honorable mention All-Big Ten from the media. He returned only eight kicks all season, but led the Hoosiers in receptions and was second on the team in yardage.
Junior year
Wynn finished second in the Big Ten with 11 receiving touchdowns. In the season opener against Indiana State, Wynn scored two touchdowns on receptions and a third score on a punt return. He scored three receiving touchdowns to close out the season in a rivalry win over Purdue. His fourteen total touchdowns are tied for sixth most in school history.
Senior year
Prior to his senior season, Wynn was elected one of the team captains. He recorded a career-high 708 receiving yards, scoring three touchdowns and adding two more scores on the ground. He averaged 96.6 all-purpose yards per game, which ranked second on the team behind All-American Coleman. Wynn capped off his college career with another win over Purdue in the Old Oaken Bucket Game. He was once again named honorable mention All-Big Ten, this time by both the coaches and media.
Professional career
Atlanta Falcons
Wynn was not selected during the 2015 NFL Draft, but shortly after the close of the seventh round, it was announced that he had signed as a free agent with the Atlanta Falcons. On June 18, 2015, he was waived by the team.
On December 2, 2015, the San Diego Chargers signed Wynn to their practice squad, replacing wide receiver Donte Foster. On December 11, 2015, the San Diego Chargers waived Wynn from their practice squad.
Wynn signed with the Jacksonville Jaguars on June 16, 2016. On September 3, 2016, he was released by the Jaguars and was signed to the practice squad the next day. He was promoted to the active roster on December 3, 2016. On September 2, 2017, Wynn was placed on injured reserve. On September 1, 2018, Wynn was waived by the Jaguars.
New Orleans Saints (second stint)
On October 17, 2018, Wynn was signed to the New Orleans Saints practice squad.
