The Bears also signed cornerback Tim Jennings, who has led the team in interceptions in each of the past two seasons, and guard Matt Slauson to four-year deals. Like Cutler, both players were scheduled to become free agents.
General manager Phil Emery said the team and Cutler's agent, Bus Cook, completed contract discussions three days after the season ended Sunday with a 33-28 loss to the Green Bay Packers in a game that decided the NFC North title. Terms were not disclosed, but the deal for the 30-year-old Cutler is reportedly worth nearly $18 million per year over the first three years and includes at least $50 million guaranteed.
"I think whenever you have two groups who want to work in the same direction and want the same thing to happen it can happen relatively pretty easily," Emery said.
Cutler produced his career-best passer rating of 89.2 in 2013, although he played in just 11 games due to ankle and groin injuries. He completed 224 of 355 passes for 2,621 yards and 19 touchdowns with 12 interceptions.
Emery said he was sold on Cutler's return after seeing him in Trestman's offense early in the season.
"After the first three games I definitely knew it was going in the right direction in terms of him putting the team in position to win games at the end of the game," Emery said. "That says a lot about the player. I think that Jay's third-down passing and fourth-quarter quarterback rating are very high and have been high for a while. He was in the top 10 in both areas this year. I think it speaks of a guy that can be a guy, a player, that is a reason you win."
Still, Emery said he wanted to see how Cutler responded to some adversity. He saw it when Cutler came back from a groin strain to face the Detroit Lions in a 21-19 loss and from an ankle sprain to beat the Cleveland Browns 38-31.
"How he handled the situation coming back from his second injury and the tremendous pressure that was on him because of the decision we had made to reinstate him as the starter, how he handled that as a person, pregame, game, within the game, after throwing a couple of picks, coming back and being a reason that you win the game," Emery said. "How he handled the Packers and Lions ... that's when I finalized the decision."
Cutler feuded with former offensive coordinators like Ron Turner, Mike Martz and Mike Tice, but he has steadily climbed the franchise statistical charts and guided the Bears to the NFC championship game in 2010.
Under Trestman, he seemed to gain a new lease on life.
"The mindset is right and the talent in the locker room is right, so I'm happy to be joining the rest of the guys, the rest of the coaches, the rest of the organization in pursuit of a championship," Cutler said.
Cutler wouldn't call money the key reason for staying out of free agency, citing familiarity with Trestman's offense as a big factor. He has only been in the same offense for consecutive years a few times in his NFL career, which started in 2006.
Trestman found Cutler ran his offense efficiently, even if he had a reputation as a big-play, big-mistake type of player.
"He's been through a lot," Trestman said. "I mean, part of what's brought him to this point is the scars of the last five years and the adversity that he's gone through in getting to know himself better over the last five years. I saw selflessness. I certainly saw mental toughness. When you evaluate a quarterback, you say, does he have an inventory of passes? Can he make all the throws? Does he have mobility? Is he a quick decision maker? Jay has all that."
The Bears tabled a few major defensive questions, including the fate of defensive coordinator Mel Tucker and whether they should stick with a 4-3 scheme.
Trestman and Emery did acknowledge the numerous injuries Tucker dealt with his first season. The Bears lost Pro Bowlers Henry Melton, Lance Briggs and Charles Tillman, as well as middle linebacker D.J. Williams, for big chunks of the season.
"I will just tell you we're going to be a younger defense," Emery said. "The draft will be focused in that area."
Nor would Trestman or Emery rule out the switch to a 3-4 defensive scheme.
"Everything is on the table in terms of a discussion," Trestman said. "Phil said it: We're going to get younger. Part of our decisions and how we move forward schematically will be based on the players that are in our locker room."