At the very least, a one-month trial with a game-managing quarterback like Josh McCown will give Trestman a window into what life without his 30-year-old starter would be like. If McCown plays well, the Bears could balk at giving Cutler a big-money deal and put the responsibility of drafting the team's next franchise quarterback in the hands of Trestman and general manager Phil Emery, neither of whom were involved in bringing Cutler to Chicago in the first place.
On Monday, Trestman announced that Cutler would miss at least four weeks after tearing a muscle in his groin during Sunday's 45-41 loss to the Washington Redskins.
“He just got grabbed and turned over and he said he felt something pop,” Trestman said, via Larry Mayer of the Bears' official site. “I’m encouraged by the prognosis that he’ll be back."
Cutler's injury comes at an awful time for the Bears, who have lost three of four games after a promising 3-0 start. In recent seasons, losing Cutler has been the beginning of the end in Chicago, as starts of 7-3 and 7-1 both went up in flames following an injury to the Bears starter.
In 2011, Cutler broke his thumb and missed the rest of the regular season. Chicago finished 1-5 without him and missed the postseason. A year later, Cutler's concussion in Week 10 began a late-season tailspin that cost Lovie Smith his job.
With his groin keeping him out a month or more, Cutler's return to Chicago in 2014—once considered close to a lock—could get considerably more unpredictable.
He's currently scheduled to become an unrestricted free agent after this season, and he'll turn 31 years old next April. To keep Cutler around, the Bears will need to spend a considerable chunk of change on a quarterback that is no longer a spring chicken.
A window for change could be opening for Trestman and Emery.
Michael Silver of NFL.com has already spoken with one source close to the situation who believes the Bears might pass on giving Cutler a mega deal and instead turn to the upcoming NFL draft for a long-term answer at quarterback.
Silver's source, on Trestman's potential thought process:
Think about it -- he had his greatest success with Rich Gannon, who was smart and moved well but wasn't anybody's idea of a big thrower. If you're him, do you want to spend $20 million a year on Cutler, who might not be the best fit, or do you want to find someone you can mold who's efficient? And if you think about how deep this (next) draft class might be, he can identify his guy and get him relatively cheap for the next few years.
Cutler's injury would certainly make any plan to move on at quarterback considerably easier.
Over the first six games, Trestman appeared to be getting through to the hard-nosed and gun-slinging Cutler. He was on pace to throw for 32 touchdowns and 16 interceptions before last Sunday, and his completion percentage and passer rating were both on schedule to set new career highs.
The Bears were also sporting a 4-2 record, thanks in large part to two game-winning touchdown passes tossed by Cutler early in the season. Despite a hurting defense giving up yards and points at a rate not typically seen in Chicago, Trestman and Cutler were holding the collective pieces together for a potential playoff team.
Sunday's loss in Washington could change everything.
Chicago not only lost the game, 45-41, and Cutler, but also linebacker Lance Briggs for four to six weeks. The two likely represent the most important players on their respective sides of the football in Chicago. If the Bears can't overcome the losses, the very real possibility of falling out of the playoff picture could surface over the next month and a half.
And while Cutler is healing up, Trestman is going to get a long look at how his offense will operate with a more manageable quarterback pulling the trigger.
Now 34 years old, Josh McCown shouldn't be billed as anything but a veteran game manager with a backup future. Before Sunday, he held a career passer rating of just 72.1 and hadn't played in a regular-season game since 2011.
Yet with Trestman's steadying hand guiding the way, McCown put together one of the finest games of his 11-year NFL career in relief of Cutler. He completed 70 percent of his 20 attempts for 204 yards and one score. He also scrambled for 33 yards, avoided turning the ball over and finished with a passer rating of 119.6.
In fact, the Bears scored 31 points after Cutler left the game and were in position to win with a defensive stop.
McCown made everything click with quick, accurate decisions. He delivered the football on time. There was an efficiency to the Bears offense that wasn't always there with the big-armed but occasionally erratic Cutler.
If Trestman can get Sunday's results with a quarterback in McCown's mold, what could he do with a young, promising rookie that fits his offense?
And given how well-adjusted some rookie quarterbacks have proven to be right away, selecting one now wouldn't necessarily mean the Bears would be stuck in some transitional period. The right player in Trestman's system could succeed theoretically succeed almost immediately, and at a fraction of the price it would cost to retain Cutler.
Matt Miller, Bleacher Report's lead NFL draft writer, calls top prospects Teddy Bridgewater, Marcus Mariota and Brett Hundley "fits" for Trestman's offense, but he readily admits all three are likely to be out of Chicago's draft range.
Will Jay Cutler be the Chicago Bears' starting quarterback in 2014?
"There are some good fits, but not necessarily first-round ones," Miller said, when asked if he viewed one or two prospects as ideal replacements for Cutler. "David Fales is a timing-based quarterback from San Jose State, but I don't love him in Round 1. Maybe someone like Zach Mettenberger from LSU, who is playing in a pro scheme now, but he's likely to be gone before Chicago drafts."
Those decisions for Trestman and Emery are still a long ways off. First, the Bears would have to swallow the sword and let Cutler walk in free agency.
While still inclined not to negotiate extensions during the season, Emery has stuck at Cutler's side despite his newest injury.
“He’s had a good year," Emery said, via Mayer. "I’ve said it in the past: I’m a Jay Cutler fan. I continue to be. He’s improved as a player. His overall demeanor and his calmness has improved. He’s certainly gotten the ball out faster. He’s hitting more targets. He’s been a key part in leading us to victory.”
For now, don't expect much change in that narrative.
No decision has a greater impact on an entire franchise than the one at quarterback. The Bears would certainly be gambling on letting Cutler—a proven commodity with a great arm—sign with another franchise next spring.
But the unpredictable Cutler isn't an ideal fit for Trestman's offense, and he's now approaching his age-31 season with an injury history that is starting to add up. If the Bears needed an excuse to initiate change, Cutler's significant groin injury could be it.