By Chris Burke
July 16, 2013

Jay Cutler owns a career record of 51-42Bears quarterback Jay Cutler owns a career record of 51-42. (John Biever/SI)

Apologies to Winston Churchill for bastardizing his famous description of Russia as "a riddle, wrapped in a mystery, inside an enigma," but there is perhaps no more apt way than that to describe the confounding NFL career of Jay Cutler.

For the past six seasons, Cutler has been a full-time starting quarterback in the NFL, first with Denver and for the past four seasons in Chicago. And for the past six seasons, everyone from fans to the media to his own coaches have tried to figure out exactly what Cutler is capable of achieving.

The latest proof that there is no definitive answer comes from a Chicago Tribune report by Vaughn McClure. He writes that the Bears had internal discussion about offering Cutler a contract extension worth about $15 million per year, "but that was before Marc Trestman took over as head coach."

Reading between the lines, it seems that Trestman may have asked Chicago's front office to hold off on locking up Cutler, whose contract runs out after the 2013 season.

And why wouldn't Trestman do just that?

The 30-year-old Cutler could be a match made in heaven for Trestman's CFL-honed offensive attack, one that will give Chicago's quarterback every opportunity to light up the scoreboard. Cutler also might disappoint again, for one reason or another, and the Bears' defense may not be as ready to rescue him as in years past.

The pro-Cutler arguments are easy to make: He should be in his prime as a quarterback, he has won 10 games twice in the past three seasons, is nine games above .500 for his career and has thrown for more than 21,000 career yards.

He's also made only one trip to the postseason -- that occurred in 2010 and ended with Cutler on the bench, claiming to be too injured to continue playing as the Bears fell to Green Bay.

Cutler's play has never fully lived up to its potential, even during those 10-win seasons in 2010 and '12. Last season, he threw just 19 TD passes (to 14 interceptions) and was downright mediocre on occasion, like a four-interception showing against the Packers. Had Chicago not finished with a top-five defense in both those 10-win campaigns, Cutler no doubt would have been expected to carry the Bears.

Even now, approaching eight NFL seasons since Cutler was drafted No. 11 overall by Denver, it's difficult to say if he could handle that responsibility. The two seasons in which he took to the air most, 2008 with Denver and 2009 with Chicago, he posted a combined 15-17 record and fired 44 interceptions.

All things considered, a $15 million per-season average is not out of line for the Bears' quarterback. Matthew Stafford, five years Cutler's junior, recently received an extension worth $15.3 million per season in Detroit, and he brings the same inconsistencies to the table. The franchise tag for QBs this season, meanwhile, was worth $14.896 million.

Still, what's the rush here for Chicago? That franchise tag option will be available next offseason, should Cutler hit free agency. (It's worth noting that the Bears have a potentially crowded free-agent class for 2014, including current franchise-tagged player Henry Melton, Charles Tillman and J'Marcus Webb.) Delaying for a year also gives Trestman that coveted evaluation period to analyze if Cutler is the player he wants to build around for the next several seasons.

There's always the possibility that this strategy will backfire. Cutler could raise his game and drop that $15 million price tag well into the rear-view mirror. Joe Flacco accomplished a similar ascension in 2012 ... and the Bears happily would trade their skepticism over Cutler for the type of Super Bowl run Flacco had.

Whenever a team hires a new head coach, there is the distinct possibility that coach will wipe the slate clean and start from scratch. Trying to do so without changing the guard at quarterback is next to impossible.

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