New England Patriots Fleming was selected in the fourth round of the 2014 NFL draft by the
New England Patriots. Fleming appeared in nine games in the 2014 season including the playoffs and won
Super Bowl XLIX with the Patriots. Fleming was a surprise cut by the Patriots at the end of the 2015 preseason but was signed to the Patriots'
practice squad. He was promoted to the active roster on October 16, 2015, after starting left tackle
Nate Solder was placed on season-ending
injured reserve with a torn biceps. In the 2016 season, Fleming played in all 16 regular-season games with five starts mainly as a reserve tackle and reporting as an extra blocker. He contributed to the Patriots' 14-2 record, which earned them the top-seed for the
American Football Conference (AFC) playoffs. On February 5, 2017, Fleming was part of the Patriots team that won
Super Bowl LI. In the game, the Patriots defeated the
Atlanta Falcons by a score of 34–28 in overtime. The Patriots trailed 28–3 in the third quarter, but rallied all the way back to win the game, which featured the first overtime game in
Super Bowl history and the largest comeback in the Super Bowl. On September 24, 2017, Fleming made his first start of the season at left tackle against the
Houston Texans. He finished the 2017 season with five consecutive starts to finish the regular season. On January 21, 2018, Fleming started at right tackle in the
AFC Championship Game, making his first career postseason start. Two weeks later, he started at right tackle in the Super Bowl, where the Patriots lost to the
Philadelphia Eagles 41–33.
Dallas Cowboys On March 26, 2018, Fleming signed a one-year contract with the
Dallas Cowboys worth up to $3.5 million. He played in 14 games, starting three at left tackle in place of an injured
Tyron Smith. On March 13, 2019, Fleming signed a two-year, $7.5 million contract extension with the Cowboys. He played in 14 games, starting three at left tackle in place of an injured Smith. On March 17, 2020, the Cowboys declined the option on Fleming's contract, making him an unrestricted free agent.
New York Giants On March 26, 2020, Fleming signed with the
New York Giants, reuniting with former Cowboys head coach
Jason Garrett and offensive line coach
Marc Colombo. He started all 16 games at right tackle in 2020.
Denver Broncos On May 20, 2021, Fleming signed a one-year, $1.67 million contract with the
Denver Broncos, after the team released offensive tackle
Ja'Wuan James. He was released in a planned move on August 31, 2021. He was re-signed on September 2, 2021. He appeared in 5 games with 4 starts at right tackle. He re-signed with the Broncos on July 27, 2022. He appeared in 15 games with 15 starts, nine of them coming at right tackle. He missed two games against the
Tennessee Titans and the
Jacksonville Jaguars because of a quad injury. The Broncos re-signed Fleming to a one year, $4 million contract on May 23, 2023. After going unsigned during the
2024 NFL offseason, he was signed to the Broncos practice squad on October 8, 2024. ==References==