In his weekly interview with ESPN 1000 in Chicago, Cutler said the reason he was wearing a boot was that there could be ligament damage to his ankle that was originally described as a "high sprain."

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“There are a couple of ligaments that we’re a little worried about that’s different than the normal high ankle sprain,” Cutler said. “There are a few other things involved. If I just had a normal high ankle sprain, I wouldn’t be in a cast. [A cast] helps it scar up and stuff, but the normal high ankle sprain isn’t really a concern at this point.”

If the injury is indeed that serious, then the idea that the Bears' starting quarterback would be ready for Chicago's December 1 matchup with the Minnesota Vikings might be a bit premature. Having Cutler in the lineup would be beneficial to the Bears' playoff chances, but we've already seen what happens when he has been left in a game with a serious injury for too long.

If you're analyzing the situation from the glass half-full perspective, look no further than the play of Bears' backup quarterback Josh McCown.  McCown has gone 2-1 as a starter in Cutler's absence, and has kept  Chicago in the thick of a heated NFC playoff race.