Will the Bears extend anyone this offseason?

Phil Emery and Marc Trestman have had a great offseason. They've added quality players like Martellus Bennett and Jermon Bushrod to long-term deals, and offset some of their key free agent departures with cheap, experienced veterans on short-term deals. But, with the Bears tight salary cap situation and impending free agent explosion after the 2013 season, shouldn't they extend at least one of their key players during this offseason?

Look, this isn't going to be a bash-Emery post, because again, I really like what he has done this offseason. If I had to give him a grade, it would be a solid A, simply because he has addressed every possible key need with a player that could and should be at least as good as the player they've replaced, if not better. But I am worried about the long-term strategy in place when you look at this information from Brad Biggs:

At present, 37 of the 70 players on the (Bears) roster will be in the final year of their deals in 2013... 11 of 22 projected starters are on an expiring contract. Same with two of the team's three specialists and returner Devin Hester.

Biggs points out that last year when the team was reporting to training camp (and had seventy players on its roster), 23 players were in the final year of their contracts. This year, having half of your roster - and half of your starters - potentially playing their last year in Chicago has got to be concerning for Emery et al. It does provide a certain amount of roster flexibility so that Emery can bring in his own guys via free agency or the draft, and forces those players to play at a high level to earn their next payday.

But the possibility of gutting your roster of half its starters in one offseason concerns me, especially considering older-ish guys like Julius Peppers and Lance Briggs are signed beyond 2013, but could be cut due to high salaries combined with diminished performance. Imagine that, in a year, all or most of those eleven starters are gone, including both starting cornerbacks, two linebackers, a safety, defensive tackle and defensive end, not to mention your quarterback and a few offensive linemen. That would cripple the franchise for a few years, regardless of how good Trestman and Emery are.

So, out of those eleven starters, who should at least be a possibility for an extension? Let's break them down into three categories: call him now!, maybe during the season, and prove it. Prove it guys need to... well... prove they deserve an extension for a whole season, then maybe we'll talk. "Maybe during the season" players I would like to see return if they can show early in the year they would be worth an extension. And "Call him now!" guys should have extensions before the season starts.

Prove It Guys: Jay Cutler, J'Marcus Webb, Roberto Garza, James Anderson, D.J. Williams, Devin Hester

Williams and Anderson are no-brainers for this category since they just signed up. I think Garza, Webb and Hester are all on their way to free agency regardless of what they do this season.

As for the other guy: here's the deal. Cutler needs to prove it. For a whole season. That's it. Whether you are on team "Cutler hasn't had ____ in Chicago" or team "Prove it Cutler," Jay needs a season of productivity to merit a return to Chicago. I want him to be good, and want him in Chicago, but he has to improve this season above and beyond what he's done in a Bears' uniform thus far.

Maybe During the Season: Matt Slauson, Major Wright, Tim Jennings, Corey Wootton

Some controversial picks here, I'm sure (although probably not as much as Cutler in the previous group for some), but hear me out. Jennings played lights out last season, but I don't know if he can replicate that for another year, let alone the balance of a contract extension that pays him like he'd be a perennial All-Pro. Major Wright has had ups and downs, but has gotten much better, and may play well enough early on to deserve an extension.

Wootton played much better last season, and if Israel Idonije doesn't return, he may be able to hold off Shea McClellin for a starting job. If he proves last year wasn't a fluke and can play even better, than he deserves a long-term deal. Slauson, despite being a newly minted Bear, may play well enough to warrant an in-season extension, because hey, he can't be worse than guard play from the recent past.

Call Him Now!: Charles Tillman, Henry Melton

Tillman is 32, yes, but I see no problem with a deal that adds two more years to his Bears' contract, reduces this year's cap number, and spreads out some money. Tillman won't have to be a Bear in the last year if they choose to cut him for performance decline, but seriously, I'd feel a lot better having Tillman under contract for at least another season.

Melton is the most likely to receive an extension, and its well-deserved. He's young, productive, plays a crucial position on the defensive line, and has been a model citizen off the field (i.e. not Cedric Benson). Yes, you may have flashbacks about Tommie Harris and his inability to live up to his big contract extension, but its not the same situation. Harris was never the same after his leg injuries. Melton has a chance to have the kind of career Harris would have had, if his body didn't betray him.