Winston chose to attend college at the University of Miami after being heavily recruited by several other schools. At Miami, Winston majored in International Finance and Marketing and played offensive tackle. He initially was set to play tight end for the Hurricanes, but made the switch before his sophomore year. Winston was widely considered one of the best offensive tackles to enter the 2006 NFL Draft. However, an anterior cruciate ligament injury during his junior year made his draft stock drop, and several draft scouting organizations expressed slight worry over the possible implications of the injury and subsequent surgery on his play. Winston was also a standout student, graduating in three years with a GPA above 3.5, and he was a 2005 All-America selection. He was a member of the Pi Kappa AlphaFraternity.
Professional career
Houston Texans
Winston was drafted in the 3rd round of the 2006 NFL Draft. He started the final seven games as a rookie at right tackle in 2006 and proceeded to start 87 games for them until 2011. He signed a contract extension prior to the 2008 season. The Texans released him on March 12, 2012.
Kansas City Chiefs
Winston signed with the Kansas City Chiefs on March 17, 2012. On October 7, 2012, Winston spoke out about Kansas City Chiefs fans, who he thought were cheering an injury to quarterback Matt Cassel. No video evidence has ever been produced to support Winston's claim. In a post game interview, he claimed "this isn't the Roman Colosseum" and "it is hard economic times". He mentioned that he came to the understanding he probably won't live as long because he plays this game, but cheering over a player getting knocked out is "100% sickening". He was released by the Chiefs on March 6, 2013.
Arizona Cardinals
Winston signed a one-year contract with the Arizona Cardinals on July 25, 2013.
Winston signed a one-year contract with the Seattle Seahawks on July 29, 2014. Winston failed to make the final 53-man roster, and was released on August 30, 2014.
Cincinnati Bengals
Winston signed a one-year contract with the Cincinnati Bengals on December 2, 2014. On March 9, 2016, the Bengals re-signed Winston to a one-year, $1.09 million contract. On March 10, 2017, the Bengals re-signed Winston to his third consecutive one-year contract. He was released on September 2, 2017. He was re-signed by the Bengals on November 8, 2017 after Jake Fisher went down with an illness.
In March 2014, Winston was elected president of the National Football League Players Association, succeeding Domonique Foxworth. Prior to being elected president, Winston had been involved with the NFLPA in other capacities, including being elected as a co-alternate NFLPA representative for the Houston Texans in 2010 and serving on committees for agent discipline and finance. He was also vocal during the 2011 NFL lockout. Winston has stated that his first priorities for his presidency will be player health and safety, financial literacy, and workplace conditions, especially in the locker room. He was succeed by J. C. Tretter in March 2020.
