Earlier this week Chris Creamer, our resident jersey and logo nerd, made us all squirm and wince when he looked back on players in the “wrong uniforms.” They had all already established themselves as legends, and would be enshrined in Canton soon after they walked away from the game.

But they weren’t ready to walk away yet, and since the teams they were so dominant with for so many years had other plans at their position, the result was some awkward pictures that are now both comical and painful. Nostalgia can be more than just a product of our memory; it’s often a powerful emotion, especially for fans of awful teams who want to reflect back on happier times. That’s what makes O.J. Simpson wearing a 49ers jersey so difficult to look at for Bills fans. I imagine that whole murder trial thing was sort of tough too.

It’s also impossible to picture Brian Urlacher wearing anything but a Bears uniform. Although the odds of that happening still seem slim, the mere fact that he’s acknowledging the possibility of a move elsewhere after this season when he becomes a free agent is already initiating my squirm reflex.

He did that today during an appearance on ESPN’s “The Waddle & Silvy Show” in Chicago. Urlacher is entering the final year of a five-year contract worth $40.6 million that he signed in 2008. He’s keenly aware of his age, and the realities of hitting the open market next March.

“I always say (I want to keep playing) two to three more years. It all depends on how I play on the field, because if I don’t play good enough, nobody is going to want me. But if I keep playing well and at a high level, then two to three more years at least, I think.”

The GLS abacus indicates that two-to-three more good years puts Urlacher at 37 on the high end of that, which is an elderly age for a defensive player who’s required to run into human brick walls in the form of offensive linemen and large running backs on nearly every play.

To his credit, Urlacher’s stayed reasonably healthy over his career, although he’s recovering from a left knee injury suffered in Chicago’s 2011 regular-season finale against Minnesota that’s limited him to only rehab work during the Bears’ offseason activities. Prior to that, his last major injury came in 2009 when he appeared in only one game because of a broken wrist that abruptly ended his season in Week 1, but he’s still only missed 22 games over a 12-year career.

He wants to stay with the Bears, and he knows the Bears want him to stay with the Bears. But CEO Ted Phillips told him that they plan to wait until the end of the 2012 season to have contract talks with their All-Pro middle linebacker. That means an adventure–albeit possibly a brief one–into the unpredictable land of free agency, which invites the possibility of changing teams, and wearing a uniform that will induce nightmares for generations.

Urlacher sounds like he’s at peace with that possibility.

“I’ll be a free agent when the season is over and whatever happens, happens. From everything that Ted Phillips said I’ll be a free agent when the season is over. It’s a business. That’s the risk you take. If you let a player get to free agency, then they can leave. That’s their (decision). They can leave if they want to. That’s how it goes.”

Recent history tells us that middle linebackers typically experience a gradual but noticeable–and to be fair, quite natural–decline as they flirt with the wrong side of 35. James Farrior wasn’t re-signed by the Steelers when he became a free agent in March, and the 37-year-old faded quickly over the past two seasons, with his foot speed the most glaring weak area. Junior Seau held on until he was 40 and continued to contribute in a limited role for the Dolphins and Patriots, but after he turned 35 he appeared in all 16 games in a season only once.

Seau was still a valuable role player on those New England teams, but not a vital cog because of the repeated beatings he’d taken earlier in his career. Oddly, though, it’s an injury that may help to prolong Urlacher’s time in the NFL.

He seemed to start his fade prior to 2009 when that wrist injury knocked him out during opening weekend. But the year of rest rejuvenated his legs, and in the years since he’s been selected to two Pro Bowls while recording 228 tackles, and for the three-year period between 2008 and 2010 Pro Football Focus named him the fourth best linebacker in the NFL.

Not bad for an old man, but his tackles still took a sharp decline last year, as he finished with his second lowest career total during a full season (102). The Bears have drafted only one linebacker over the past two years (J.T. Thomas in the sixth round in 2011), and next spring they’ll have to decide if they want to spend a valuable early-round pick on Urlacher’s eventual replacement.

If he stays healthy and makes his fade gradual, then he’ll get his wish to retire as a Bear. If not, there’s a chance he could leave us with forgettable pictures to mock years from now.