A native of the Liberty City neighborhood of Miami, Thompkins attended Miami Northwestern High School. A classmate of NFL cornerback Anthony Gaitor, Thompkins started for Northwestern, but was academically ineligible to play as a sophomore and was later expelled for violating school policy. He was allowed to re-enroll prior to his junior football season, only to be expelled again later in the year. After spending his junior year at an alternative school, he re-enrolled at Northwestern for the third time prior to his senior year and finished his high school football career. Not long after the season concluded, Thompkins was expelled for the third time, after being arrested on armed robbery charges. After seven mostly drug-related arrests Thompkins was barely recruited coming out of high school. His only scholarship offer was from Morgan State, but he never enrolled.
College career
Thompkins briefly attended Palomar College in San Marcos, California in 2008 before transferring to El Camino College in Torrance, California to play football. At El Camino College, Thompkins recorded two 1,000-yard seasons in a row, being named a team captain as a sophomore. Following his sophomore campaign, Thompkins signed with the University of Tennessee in order to play under then-coach Lane Kiffin; following Kiffin's departure to become head coach of the USC Trojans football team, Thompkins transferred to the University of Oklahoma Sooners, but did not play at either university, as Oklahoma has a strict policy against admitting students with a history of legal troubles. Instead, Thompkins transferred to the University of Cincinnati, where he played for two seasons from 2011 to 2012. As a junior in 2011, Thompkins caught 44 passes for 536 yards and two touchdowns. As a senior in 2012, he recorded 34 receptions for 541 yards and two touchdowns.
Thompkins signed with the New England Patriots as an undrafted free agent on May 3, 2013. In his preseason debut, Thompkins registered 4 receptions for 23 yards with the first-team offense against the Philadelphia Eagles. In the third game of the season, Thompkins caught the first two touchdown passes of his career to help the Patriots win the game 23–3 against the Tampa Bay Buccaneers. In Week 6's matchup against the undefeated New Orleans Saints, Thompkins caught the game-winning touchdown on a 2nd down play with 5 seconds remaining in the game. Thompkins was released by the Patriots on October 4, 2014.
Oakland Raiders
Thompkins was claimed off waivers by the Oakland Raiders two days after his release from the Patriots, on October 6, 2014. He caught 15 passes in 12 games for 209 yards with Oakland and was cut by Oakland on September 1, 2015.
New England Patriots (second stint)
The Patriots re-signed Thompkins to their practice squad on September 6, 2015. He was released from the practice squad on September 30, 2015.
On October 2, 2015, the New York Jets signed Thompkins to their practice squad. He was promoted to the active roster on October 20, 2015 after Quincy Enunwa was suspended. On September 3, 2016, Thompkins was released by the Jets as part of their final roster cuts. On August 16, 2017, Thompkins re-signed with the Jets. On September 2, 2017, Thompkins was released by the Jets.
