Cutler has one year left. He is 30 years old, and despite a 34-22 regular-season record with Chicago, he has not proved to be worth what the Bears gave Denver to get him four years ago. Two first-round picks and a third were a high price for a quarterback who has guided his team to just one postseason appearance.
To earn a new deal, Cutler must lead Chicago into the playoffs, and once there, he must win. It is as simple as that.
So Chicago will wait and see and evaluate and let Cutler twist in the uncertainty of a contract year. Baltimore's Joe Flacco flourished under such pressure, but unlike Cutler, Flacco brought that pressure on himself. He made the calculated decision last summer that he was worth more than the Ravens were offering, and he went out and backed it up in the most impressive -- and ultimately lucrative -- way possible.
How will Cutler react under similar pressure? Chicago general manager Phil Emery has done everything he could to support Cutler and help him be successful. In Marc Trestman, Emery hired a known quarterback guru who tutored Steve Young, Bernie Kosar, Rich Gannon and Jake Plummer, among others.
Trestman will call the plays and has provided Cutler a direct line of communication to the head coach. They will plan together. They will brainstorm together. And they will work in tandem on game days, something Cutler never had with former Bears head coach Lovie Smith.
Emery also has spent the past two offseasons providing Cutler with the weapons he desired. He signed Cutler's friend, Brandon Marshall, who last season caught 118 passes for 1,508 yards, second only to Detroit's Calvin Johnson. Emery traded up in the second round of the 2012 draft to select Alshon Jeffery, a 6-foot-3 receiver out of South Carolina, and then drafted for need in the first round this year, selecting Oregon guard Kyle Long 20th overall.
In a continuing effort to upgrade an offensive line that has allowed Cutler to be sacked 153 times in four years, Emery signed New Orleans tackle Jermon Bushrod to the largest contract the Bears have ever given an offensive lineman and guard Matt Slauson from the Jets. He also signed tight end Martellus Bennett.
Now, it is up to Cutler.
It is pretty simple. Emery has set the bar. Chicago started last season 7-1, lost five of its final eight games and finished 10-6, missing the playoffs by one game. That cost Smith his job, even though a 10-6 record was good enough in 2011 to get Atlanta and Detroit into the playoffs. Smith didn't lead the Bears into the postseason. That was all Emery needed to make a coaching change.
So there it is. With Smith as the guide, Cutler must get the Bears into the playoffs, and he needs to get them deep into the playoffs before the team commits to him long term. He must do it with a first-year NFL coach and playing in his fourth offensive system in five years.
There is more that goes into it. Surely Trestman would like to see Cutler avoid taking unnecessary sacks. He'd like to see him utilize Matt Forte in a West Coast system that is perfect for Forte's array of skills. He'd like to see him spread the ball around and not rely on Marshall so much. He'd like to see Cutler's completion percentage well north of 60 percent, which would be a first in Cutler's Chicago career.
Trestman would like to see Cutler excel at the short and intermediate passes that are a staple of the West Coast offense, and then utilize his arm by taking a calculated shot downfield when the opportunity presents itself. He would love for Cutler be the leader Brian Urlacher was, who could set the example and keep the team focused when the inevitable bump occurs. Trestman would like Cutler to be an extension of himself with the players, which might be too much to ask for a guy who has been historically prickly and unpopular.
But most of all, Cutler must show he can win in January.
The Bears should expect Cutler to lead them to the postseason, win a game or two and show that he is one of the NFL's elite quarterbacks. Then and only then should Chicago sign Cutler to a new contract. Then he will deserve it. Then he will have proved he was worth all Chicago gave up to get him.
If he finally delivers on his potential, Cutler can forget about all the questions about why Denver traded a quarterback with his tools in his prime. Chicago would know, too, that Cutler is mentally strong enough to withstand a coaching change and have success in a new offense while learning on the fly.
Cutler has said it takes three years to learn a new offense. He doesn't have three years. He has one. This one.
Rodgers and Stafford got the new deals they coveted. Cutler can get his, too, but he will have to wait and work and still be playing when the calendar flips to 2014.