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In 2009, he was traded to the Chicago Bears, where he played for eight seasons.
Following the 2016 season, Cutler announced his retirement and his intention to become a sportscaster for NFL on Fox's television broadcasts.
He is the third first-round pick to come from Vanderbilt, preceded by Will Wolford and Bill Wade.
The question facing FOX is whether five people can work together seamlessly, or whether the crew will have a “too many cooks” feel to it.
FOX wants Thursday nights to feel like a big deal, and it remains to be seen whether the broadcast team is too big.
Cutler and his team outscored opponents 746–85, including a 90–0 shutout at Pike Central.
During his senior year, Cutler connected on 122 of 202 passes (60.4%) for 2,252 yards with 31 touchdowns, while rushing 65 times for 493 yards with 11 touchdowns.
However, following a season-ending injury to Miami Dolphins quarterback Ryan Tannehill in August 2017, Cutler came out of retirement and signed a one-year deal with the team.