Quarterback Jay Cutler is an enigmatic figure whose flashes of brilliance were usually overshadowed by questions of motivation and unfulfilled hopes. Born in Santa Claus, Ind., and a Bears fan growing up, Cutler attended Vanderbilt where he was the 2005 SEC Offensive Player of the Year. In 2006, he was drafted 11th overall by the Broncos and in his third season, at age 25, threw for 4,526 yards and made the Pro Bowl. The 6-foot-3, 231-pound Cutler was traded to Chicago with high expectations in 2009, where he became an immediately controversial figure. In his first season with the Bears, he threw a league-high 26 interceptions and, over the course of eight seasons with Chicago, developed a reputation as a player with extraordinary physical gifts but who was aloof and not realizing his potential. Over his Bears’ tenure, he made no Pro Bowls and went 51-51, leading them to the playoffs just once. Nonetheless, he retired as the franchise’s all-time leader in numerous categories, including passing yards, touchdowns, and regular season wins by a QB. He played with the Dolphins in 2017 before retiring for good.