Thearon W. Henderson/Getty Images
This is the million dollar question that could determine how the Bears do in 2013 and what they do going forward.
While some question the mesh of their personalities, it's about scheme and style. Trestman wants his quarterback to protect the ball at all costs, while Cutler has been known to take risks and put the ball where it shouldn't go.
In Cutler's defense, it has been hard to find where the ball should go in the Bears offense. Their receivers have struggled to get open and their line has been among the worst in the league since he came to Chicago.
After having 15.9 percent of his passes travel over 20 yards in the air in 2012—the fourth highest rate in the league, according to Pro Football Focus (subscription required)—Cutler will be getting rid of the ball quicker this year under Trestman.
Just three—8.8 percent—of his passes travelled that far in the preseason, according to Pro Football Focus (subscription required). While that number will likely increase when the regular season starts, it's a clear sign that the Bears will use the short passing game to open up plays down the field.
The result has been a higher completion percentage. He's completed 64.7 percent of his throws this preseason, after finishing below 59 percent the last two years. His preseason completion percentage would be much higher if not for a handful of drops against Oakland.
We've still seen some of his recklessness, however.
He's thrown two interceptions, both on throws that were off the mark. His first one came on his first pass of the preseason in a throw to Alshon Jeffery. While Jeffery should share the blame on that play for not fighting for the ball, it was still a turnover that never should have happened.
The second interception was a bad read, bad throw and the exact kind of play he can't make.
That said, part of what makes Cutler good is his ability to make big plays when nothing is there. While that also leads to some mistakes, most of those plays end up being good for the Bears.
Trestman can't make him into a "Check Down Charlie," or the Bears offense won't operate as well as it could.
They have to find a common ground. Cutler still has to be able to trust his instincts and arm and Trestman has to let him do that, just not as often as he'd like.