After Romo's and Flacco's Deals, the Stakes are Raised for Jay Cutler

Jay Cutler's all set for a make-or-break season. Since the trade to Chicago that brought him here in 2009, Cutler's not yet returned to the Pro-Bowl form of his 2008 season that Bears fans were convinced was going to solve their quarterback problems once and for all.

Over the last four years, let's recap the changes that have occurred in the name of a productive offense:

• Signed Orlando Pace, Pace Retired, Chris Williams goes back to left tackle, J'Marcus Webb took over at left tackle, and the Bears signed Jermon Bushrod.
• Lance Louis left for Miami, and the Bears signed Matt Slauson.
• The offensive coordinator cycle spins from Ron Turner to Mike Martz to Mike Tice to Aaron Kromer and Marc Trestman, the new head coach after the firing of Lovie Smith.
• The Bears upgraded their receiving corps by adding Brandon Marshall and Alshon Jeffery.
• The Bears went from Greg Olson and Brandon Manumaleuna to Kellen Davis and Matt Spaeth to Martellus Bennett and Steve Maneri.

Get all that? I probably missed something, but that's not the point.

The point is that Jay Cutler is the crux of the offense, for better or worse, and the team has spent the better part of four years trying to adjust things to get the most out of the quarterback they traded a bounty for. Giving up two first round draft picks makes it hard to build around him, but the offense wasn't ready to accept a new big-time quarterback.

Now, the question becomes his standing for next season.

This week, Tony Romo and the Cowboys agreed to a six-year, 108-million-dollar ($40-million guaranteed) contract in the wake of Joe Flacco's "richest NFL player ever" contract for six years and 120.6 million (29 guaranteed). Whether or not you think Romo or Flacco deserve those contracts is one thing (spoilers: hell no). The fact they have them is another thing.

It's these contracts that help set the market for Cutler's contract if he performs well in 2013, even if you think the Romo contract is like the DeAngelo Williams deal compared to Matt Forte.

The last couple years, Cutler's cap hit has been between 8.9 and 9.6 million. This year, it's up to 10.37. If Cutler has a great year, are you prepared to watch that cap hit rocket towards the 15s, 18s or even the 20s? Yes, you'd have a player with (possibly) two Pro Bowls to his name and hopefully a Super Bowl. Is one year of high-caliber quarterback play after four years of not-so-great worth paying that much for?

Don't get me wrong - in order to get a solid player, you have to pay more than you'd like on occasion, I understand that. But remember how you got that player there - by upgrading every single thing around him, sometimes multiple times. If you work to upgrade everything around the player over five years (it's been five years already?!), how much of the quarterback's improvement is the quarterback and how much is everything else?

Jay Cutler might not be worth much more than he's already making, because of how much the team has had to change to get him (potentially) to that point.