Now, after a stormy exit from Denver, he's the franchise quarterback for his once-favorite team.
One thing, though. Don't call him a savior.
"I don't see myself as that," Cutler said Friday.
The Bears dealt quarterback Kyle Orton along with two first-round draft picks and a third-rounder to the Broncos for Cutler and a fifth-rounder on Thursday. They also agreed to a three-year contract with free-agent Orlando Pace, filling a hole on the offensive line with a seven-time Pro Bowler for St. Louis.
The Bears showed they're serious about contending in the NFC after missing the playoffs the past two years, and in Cutler, they finally have a top-tier passer after a decades-long search.
"Time will tell if he's going to be a franchise player," general manager Jerry Angelo said. "We're certainly hoping that's the case. But what we do know is we got a winning quarterback and we feel very good about that."
The Bears are getting a Pro Bowl quarterback who threw for 4,526 yards, 25 touchdowns with 18 interceptions, yet got traded after a major blowup with management and new coach Josh McDaniels.
"This is kind of a new chapter for me and I'm excited to be here," Cutler said Friday.
If he performs as advertised, the Bears will finally have a mobile quarterback with a rocket arm who will bring an end to mediocrity at the position.
"He does for us what Ben Roethlisberger does for the Steelers," said tackle Chris Williams, Cutler's teammate at Vanderbilt.
In Denver, Cutler had to live up to the legacy of John Elway. In Chicago, he can create one of his own.
Twenty-three quarterbacks have started for the Bears since Jim McMahon in the mid-1980s, but the quarterback problems date back about six decades, since the days of Hall of Famer Sid Luckman.
"This is like my second draft day," Cutler said.
When he arrived in Denver, he couldn't escape the comparisons to Elway.
"It was, 'How are you going to fill his shoes? What are you going to do to be like John Elway?'" Cutler said.
In Chicago? "I'm going to have to do some research on Sid," Cutler said, grinning.