He played college football for the Maryland Terrapins, and was selected by the Oakland Raiders seventh overall in the 2009 NFL draft.

Heyward-Bey attended the McDonogh School in Owings Mills, Maryland, where he played football as a wide receiver and linebacker.

[citation needed] That season, he was considered one of the top rookies in the Atlantic Coast Conference (ACC) and earned first-team freshman All-America from the Sporting News and Rivals.com.

[citation needed] He led the Terrapins with 45 receptions, and set a school record for a freshman with 694 receiving yards.

[18] As the first wide receiver selected, he was picked earlier than most projections, and before Michael Crabtree and Jeremy Maclin, who most analysts thought would precede Heyward-Bey.

[20] During organized team activities following the draft, Heyward-Bey practiced early but was plagued by multiple hamstring injuries.

[26] Vittorio Tafur of the San Francisco Chronicle highlighted Heyward-Bey's performance in the game as a marked improvement from the preseason.

[27] On October 31, in a 33–3 victory over the Seattle Seahawks, Heyward-Bey made a career-long 69-yard touchdown reception from Jason Campbell, part of a career-high of 105 receiving yards.

[43] He entered his first training camp with the Steelers competing with Lance Moore, Derek Moye, Martavis Bryant, and Justin Brown for the third wide receiver position.

[48] Following the release of Lance Moore on March 2 and the four-game suspension of Martavis Bryant on August 31, Heyward-Bey became the Steelers' third receiver behind Antonio Brown and Markus Wheaton to begin the 2015 season.

[49] The following week against the San Francisco 49ers, Heyward-Bey again caught four passes, this time for 77 yards and one touchdown, marking his highest receiving yardage total since December 6, 2012.

[53] He entered training camp competing to be the second or third wide receiver on the Steelers' depth chart, with Martavis Bryant suspended for the entire 2016 season.

[58] Heyward-Bey entered training camp in 2017 facing stiff competition for the backup wide receiver position from JuJu Smith-Schuster, Cobi Hamilton, Eli Rogers, Sammie Coates, and Justin Hunter.

He was initially named the fourth wide receiver behind Antonio Brown, Martavis Bryant, and Rogers, but was passed on the depth chart by Smith-Schuster early in the season.

[60] He earned his first passing target and reception in Week 7 against the Cincinnati Bengals on a fake punt when he and teammate Robert Golden connected for 44 yards.

Heyward-Bey's mother, Vivian, a certified accountant, has helped him save much of his career earnings, despite the majority of it having been his rookie deal in 2007.