He played college football for the Florida State Seminoles, becoming the youngest player to win the Heisman Trophy and leading his team to victory in the 2014 BCS National Championship Game during his freshman year.

Winston set several franchise rookie records for the Buccaneers, earning him Pro Bowl honors, and led the league in passing yards during the 2019 season.

After his rookie contract with the Buccaneers expired, Winston joined Tampa Bay's NFL South divisional rival New Orleans Saints, where he alternated as a starter and backup for four seasons.

Though the Rangers proposed allowing him to play for the Florida State Seminoles football team while working out with their baseball organization, Winston decided not to sign.

[13] Winston helped lead the team to an undefeated 13–0 regular season record, including a 45–7 victory in the Atlantic Coast Conference (ACC) Championship against Duke.

[24] Most notably, he won the Heisman Trophy on December 14, 2013, beating out quarterbacks A. J. McCarron, Jordan Lynch, and Johnny Manziel, the previous winner, as well as running backs Tre Mason and Andre Williams.

[34] After a 13–0 regular season, the Seminoles were selected to play in the 2015 Rose Bowl, a semifinal game in the College Football Playoff, against Oregon.

[50] Winston played his first regular season game against the Tennessee Titans that featured fellow first rounder, Marcus Mariota.

He was named to the NFL All-Rookie Team for his 2015 season, becoming the fourth Buccaneers quarterback to receive this award, joining Tom Owen (1974), Doug Williams (1978), and Mike Glennon (2013).

[57][58][a] Winston's second season in the NFL began with an impressive performance against the Atlanta Falcons at the Georgia Dome, in which he completed over 70% of his throws for 281 yards and four touchdown passes in a 31–24 victory.

[59][60] Following Week 1, the Buccaneers began to struggle through injuries, inconsistent play, and offensive turnovers till mid-season, at which point the team was 3–5 and had experienced blowout losses to the Arizona Cardinals, Denver Broncos, and Atlanta Falcons – a three-game losing streak.

The win streak gave the Buccaneers possession of the 6th seed in the NFC playoff race, which they quickly lost after back-to-back losses to the Dallas Cowboys and New Orleans Saints.

[68] In the game, Winston became the second-youngest player in NFL history to reach 10,000 career passing yards, four days older than record holder Drew Bledsoe.

[72] On June 21, the NFL announced that he would be suspended for violating the league's personal conduct policy, regarding his latest incident where he allegedly groped a female Uber driver.

[88] Two weeks later, in a 27–23 loss to the Titans, Winston broke another Buccaneers franchise record, previously held by Testaverde, for career passing attempts, but finished with 301 yards, two touchdowns, two interceptions, and two lost fumbles.

[110] In the Divisional Round of the playoffs against the Tampa Bay Buccaneers, Winston went into the lineup on a trick play and threw a 56-yard touchdown pass to Tre'Quan Smith during the 30–20 loss.

[114] The following week against the Panthers with multiple starters injured and seven coaches sidelined due to COVID-19 Winston threw for 111 yards and 2 interceptions with no touchdowns in the 26–7 loss.

[116] In Week 8 against the Buccaneers, Winston had to leave the game in the second quarter due to a knee injury after being horse-collar tackled by Tampa Bay linebacker Devin White.

[124] After starting quarterback Deshaun Watson was ruled out for the season with an Achilles tear on October 20, Winston took over as the starter beginning in Week 8.

The Browns squandered that lead after a pair of turnovers from Winston in the fourth quarter, but he rallied Cleveland to a game-winning drive with under a minute left to win 24–19.

[129] Winston was replaced by Dorian Thompson-Robinson late in the second half of the Browns' Week 15 game against the Kansas City Chiefs after throwing three interceptions in a 21–7 loss.

[154] On November 14, 2013, the State Attorney of the Second Judicial Circuit announced they were opening an investigation into a sexual assault allegation involving Winston that was originally filed with the Tallahassee Police Department (TPD) on December 7, 2012.

[158] Tallahassee police stated that the complaint was made inactive "when the victim in the case broke off contact with TPD, and her attorney indicated she did not want to move forward at that time" and then re-examined after media requests for information started coming in early November.

[159] On December 5, 2013, State Attorney Willie Meggs announced the completion of the investigation and that no charges would be filed against anyone in this case, citing "major issues" with the woman's testimony.

[165] The investigation was conducted by Officer Scott Angulo, who, the Times' article notes, did private security work for the Seminole Boosters, the primary financier of Florida State athletics.

[164] The official FSU hearing, presided over by retired Florida Supreme Court Justice Major B. Harding, on December 21, 2014, cleared Winston of violating the student conduct code in the sexual assault allegation.

[173] In 2016, the university paid $950,000 to settle a lawsuit brought by the same woman alleging a violation of Title IX by FSU in handling her complaint.

[175] On April 29, 2014, Winston was issued an adult civil citation for shoplifting crab legs from a Tallahassee Publix store.

[178] Two days later, university president Garnett S. Stokes and athletic director Stan Wilcox, citing results of an "ongoing investigation", announced that Winston would be suspended for the whole game.

[180][181] Two days later, it was revealed that Ronald Darby, who also attended Florida State, was also on board during the ride in which this incident supposedly occurred.