Jay CutlerJay Cutler has lived a semi-charmed life. He was selected with the eleventh overall pick of the

2006 NFL Draft. He spent three seasons with the Broncos and was selected to the Pro Bowl. He was traded to the Bears in 2009.

With the Bears, he has had the career of a vagabond of sorts, winning and being criticized for being injured in the NFC Championship Game, a flame thrower with good receivers to catch the ball for him and a running game that has featured one of the better backs in the league.

Still, there are a million reasons to question why the Bears felt the need to re-sign Cutler to a new seven-year, $126 million contract. It’s puzzling in that Josh McCown appeared to be the better quarterback on the Bears' roster this season and Cutler, for all his strong-armed talent, hasn’t been the “John Elway” the franchise hoped he would be.

So call this the curious case of the quarterback who got what he may not have deserved.

Despite injuries and controversy over his worth to the franchise, Cutler finished the season completing 224 of 355 passes for 2,621 yards, 19 touchdowns, 12 interceptions, and a career-high 89.2 passer rating. He also became the team’s all-time leader in passing yards, passing Sid Luckman before he signed the contract extension after the first of the year and in doing so, meaning Phil Emery, the team’s general manager, basically signed his extension or his death certificate with the Bears organization over this one.

There is no way to judge whether this was the right move on the Bears’ behalf. Cutler is certainly the most talented quarterback the franchise has ever had. Here might be the litmus test.

Is he on par with Tony Romo or Matt Ryan? Both quarterbacks signed huge contracts in the offseason last year. Romo had one of his better seasons with less statistics and no playoff appearance.

Ryan was thought to be the next to take the step forward this season and he and the Falcons had a dismal season.

Honestly, Cutler is better than Ryan at this point and may be on par with Romo or slightly ahead, but both cannot win the big game.

So when we look at the body of work and the rush to make Cutler the “Man” in ChiTown, you have to wonder if the franchise overreacted and struck quickly when it could have slow played this. Did losing Cutler in free agency really mean a lot when McCown was successful in his stead?

I guess that is something Emery and the Bears’ brass will eventually have to ask.