A native of Miami, Flowers originally attended Krop High School in the Ives Estates, where he was a basketball standout and did not focus on football until his junior year. For his senior year, he transferred to Norland High School in Miami Gardens, where he joined a talented varsity that featured blue chiprunning backDuke Johnson. Flowers helped the Vikings to a 15–0 season record and a FHSAA Class 5A championship over Crawfordville Wakulla. Regarded as a four-star recruit by Rivals.com, Flowers was ranked as the 20th-best offensive tackle in his class. ESPN labelled him a three-star recruit and ranked him 57th in his position. He chose Miami over offers from Purdue, Florida State, and Central Florida.
College career
As a true freshman at the University of Miami in 2012, Flowers played in all 12 games at right tackle, making four starts. As a sophomore in 2013, he started all 12 games at left tackle. He returned as the starting left tackle in 2014. On December 29, 2014, Flowers announced that he would forgo his senior season and enter the 2015 NFL Draft.
On April 30, 2015, Flowers was selected with the ninth overall pick by the New York Giants in the 2015 NFL Draft. He was the highest selected Miami Hurricanesoffensive lineman since Bryant McKinnie in 2002. On June 18, 2015, Flowers signed a 4-year $14.3 million contract with the Giants. He was named the Giants starting left tackle for Week 1 and played in 15 games in his rookie season. Although he wore number 76 jersey throughout his entire rookie season, Flowers decided to switch to his college number 74 during the spring of 2016 after it was left available with the departure of teammate Geoff Schwartz. Flowers has been criticized for not living up to expectations through his 3rd year in the league. Since he gave up 169 total pressures which is the most of any tackle in the NFL during that time. Those stats and his numerous penalties have caused Pro Football Focus to rate him as the 54th best tackle in the NFL. In 2018, former offensive line teammate and NFL analyst Geoff Schwartz accused Flowers of "quitting" on the team, of missing multiple blocks, and of having poor technique. On May 2, 2018, the Giants declined the fifth-year option on Flower's contract, making him a free agent in 2019. He was moved over to right tackle after the Giants signed veteran Nate Solder to be their left tackle. On September 23, 2018, the Giants decided to bench Flowers in favor of Chad Wheeler at right tackle after his continued struggles. On October 8, 2018, the Giants announced plans to release Flowers if a trade with a team couldn't be worked out. The next day, Flowers was officially released by the Giants.
Jacksonville Jaguars
On October 12, 2018, the Jacksonville Jaguars signed Flowers to a one-year contract after Josh Wells was placed on injured reserve. He was named the starting left tackle in Week 11, and started there the rest of the season.
Washington Redskins
On March 18, 2019, Flowers signed a one-year, $4 million contract with the Washington Redskins. He transitioned to offensive guard during the team's training camp, where he started all season at left guard.
Miami Dolphins
On March 20, 2020, Flowers signed a three-year, $30 million contract with the Miami Dolphins.
