He grew up in southern Indiana worshiping the Bears, appreciating their tradition. He understood the high expectations placed on their quarterbacks even though the last great one, Sid Luckman, roamed Wrigley Field long before Cutler was born.
But as he eagerly awaited the phone call that would determine his future, Cutler never fathomed landing with the team of his dreams.
"I was thinking Washington," Cutler said of the Redskins. "That was the strong rumor that was out there. ... I think Washington was kind of on everybody's radar.
"This came out of the blue."
Bears fans would say straight from heaven.
General manager Jerry Angelo beamed as he entered the interview room Friday at Halas Hall and took a seat next to Cutler, possibly the franchise quarterback the organization has sought for eons. Angelo even took a moment to thank the media for the positive press related to his bold trade for Cutler, the 25-year-old Pro Bowl gunslinger whose strong arm might change the complexion of Bears football.
The buzz about Cutler already has been felt throughout the city. Angelo realized it when he heard a Bears fan from St. Louis rambling on Sirius radio. The fan was so stunned, he couldn't get his words out properly.
"I'm really shocked by it," Angelo said of the positive vibe. "I knew we'd create some new energy. But it's almost like a tsunami type of energy."
For Cutler, the last few days have been a whirlwind. Once he got word of the trade from agent Bus Cook, he scrambled to purchase a new suit to make a good first impression. He started his introductory news conference by thanking the McCaskey family, Angelo and coach Lovie Smith for the opportunity.
Cutler, whose spat with new Broncos coach Josh McDaniels over McDaniels' inquiries into trading the quarterback led to Cutler's exodus from Denver, even acknowledged Broncos owner Pat Bowlen and the Broncos fans for their support.
"Obviously there has been a lot said, on my part and the Broncos' part, over the last couple of months," Cutler said. "I think both sides would possibly do a few things differently. But everything happens for a reason. That's behind."
Hours before Cutler fielded questions in Chicago, McDaniels addressed the media in Denver to offer his final take on the fallout. The divorce apparently became final after McDaniels claimed Cutler refused to return calls from the organization.
"It was going to require a two-way commitment," the coach said.
McDaniels also said it wasn't true he didn't clue in Cutler to the trade talks that sparked the firestorm. He said he informed Cutler and Cook on Feb. 28 that he had received a phone call that morning asking if he would be willing to part with Cutler in a three-way deal.
"That morning, we told them that there were some people who had called about an issue with [Matt] Cassel, that we had talked to them, that we did not initiate the contact, that that's where it stood," McDaniels told the Associated Press.
Cutler declined to go into details about the matter.
"I'm not going to rehash and go down that whole road again," he said. "The bottom line is, I'm a Chicago Bear. And I'm happy to be here."
"I don't see myself as that at all," he said. "In this league, I think I've learned over my past three years that it takes offense, it takes defense, it takes special teams and it takes great coaching. If you don't have all four of those, you're not going to go very far."
Cutler vowed first to win over his teammates. Friday was a good start.