Gilbert's father Jeff was a Secret Service agent who protected Barack Obama during his 2008 presidential campaign.

During the Gators 2008 BCS National Championship season, Gilbert started two games at left guard against Hawaii and Miami.

He started in all 14 games for the Gators at right tackle in 2009, and earned SEC Offensive Lineman of the Week honors for his performance against Kentucky on September 26.

He participated at Florida State's Pro Day and nearly finished the entire workout before reinjuring his hamstring during a 40-yard dash.

[5] Gilbert was the ninth offensive tackle selected in the 2011 NFL Draft, where being chosen by the Pittsburgh Steelers reunited him with his former Florida teammate Maurkice Pouncey.

[8] September 18, 2011, Gilbert made his professional regular season debut and his first career start in a 24–0 victory over the Seattle Seahawks.

He was named the starting right tackle after Willie Colon was placed on injured-reserve after tearing his triceps during the season-opener against the Baltimore Ravens.

[9] During a Week 5 matchup against the Tennessee Titans, Gilbert let the game after suffering a shoulder injury and was replaced at right tackle by Jonathan Scott.

During the Pittsburgh Steeler's training camp in 2012, Gilbert competed with veterans Max Starks, Chris Scott and rookies Mike Adams and Kelvin Beachum for a starting tackle position.

[15] On October 20, 2014, Gilbert suffered a concussion and left during the second quarter of 30–23 victory over the Houston Texans on Monday Night Football.

[16] He was limited to 12 starts in 2014 after he missed Weeks 13, 14, and 15 after suffering an ankle injury during practice and was replaced by Mike Adams for those three games.

Gilbert started 13 games and finished the season ranked the 13th best offensive tackle by Pro Football Focus with an overall grade of 87.1.

[26] On March 8, 2019, the Steelers agreed to trade Gilbert to the Arizona Cardinals in exchange for a compensatory sixth round pick.

[32] On February 22, 2021, Gilbert married political commentator, congressional candidate and former Miss Ohio, Madison Gesiotto.