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.
Two big moves. One big statement.
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."
And just when things were starting to smooth out, Cutler found out in late February that the Broncos were trying to trade him to Tampa Bay in a three-way deal that would have sent Matt Cassel from New England to Denver.
Cutler and his agent didn't think McDaniels was up front with them about the trade talks and asked to be dealt; McDaniels, however, insisted he informed Cutler the morning of those discussions. Cutler declined to discuss the timeline on Friday, saying, "This is kind of a new chapter for me and I'm excited to be here."
Either way, two meetings that were supposed to ease the tension in Denver only escalated the ill will, even though McDaniels insisted Cutler was his quarterback.
Cutler even said earlier this week that he didn't want to leave Denver, yet that's exactly what happened.
He initially figured he'd wind up with the Washington Redskins, but he got sent to Chicago, with a chance to repair his reputation.
"I think in time, everyone will get a clearer picture of what I'm about on and off the field," Cutler said. "Whenever you make this decision, you either have to go at it full speed or not at all because there's going to be some stuff out there that's said that might not be true."
If he performs as advertised, the Bears will finally have a mobile quarterback with a rocket arm who will bring an end to the long line of mediocrity at the position.
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.
"I'm going to have to do some research on Sid," Cutler said, grinning.
He will certainly miss throwing to Brandon Marshall and Eddie Royal and setting up behind a line that allowed him to be sacked just 11 times while throwing 616 passes. Cutler figures to be well-protected if Pace stays healthy and Williams performs as expected in his second season.
Devin Hester struggled with a bigger role on offense and saw his production on special teams drop after two record-setting seasons returning kicks. Rashied Davis struggled to hang onto the ball, and Earl Bennett didn't catch a pass as a rookie after being drafted in the third round out of Vanderbilt.
"I'm excited about what we have here," Cutler said.