He’s the oft-criticized quarterback of the Chicago Bears, and he’s a bit of a dick.

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Hey, so… You’re pretty hot and I don’t hate you. We should maybe get married. Or not. See if I care.

[Kristin Cavallari, Jay Cutler Engaged: PEOPLE]

Their dates were probably dressed like a couple of Ho Hos.

Via Deadspin

I’m sorry, Jay Cutler, that your toughness came into question while we were getting our asses handed to us by the Packers on Sunday. You had a Grade II sprain of your medial colateral ligament, which is the ligament that the banks take away when you don’t pay your medials on time. Are you having money problems, Jay? I’m always here to help you out, buddy. Look, there’s an ATM right over there.

Little did you realize, Jay Cutler, that as you stood on the sideline in the second half that members of your football fraternity would say mean things about you on the internet. I just want you to know that I would never have done such a thing, since it’s against league rules to tweet during games. I don’t understand how they could have said things about you like I might have done 18 months ago. I can say those things because we’re like a family, so it’s different. We’re a football family, with black babies and white babies. And when the babies misbehave or get too old, they’re killed. Babies don’t live forever, Jay.

I want you to know, Jay Cutler, that you are the toughest quarterback I have ever played with. That’s right. Tougher than Rex Grossman. Tougher than that guy with the beard. Tougher than Cade McNown. And yes, tougher than even the great Craig Krenzel. You are tougher than all of them, Jay, though I’m pretty sure Brad Maynard would own you in a barfight.

So I guess…have a good offseason, man. Try not to take any stairs or anything.

All I wanted to do was call Vanderbilt gay, but I like the direction this went. And while it doesn’t fit in with the “Whatever” version of Jay Cutler we’ve envisioned at KSK, the @NotJayCutler Twitter feed is probably as close to reality as good ol’ @KingLaserface. Which is to say: VERY close.

I’m sorry, but my only feelings on the potential trade involving Jay Cutler, Jason Cambpell, and a first round pick or three can only be articulated after the jump.

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Inter-sport Cutler trade is imminent! KSK has learned from sources adjacent to the situation that the Denver Broncos are preparing to pull the trigger on a historic three-team trade that would send quarterback Jay Cutler to the Memphis Moon Grizzles in exchange for small forward Rudy Gay, Space Bear, and the entire staff of 3 Shades of Blue. The rest of the deal involves Washington’s Chris Cooley heading to Denver in exchange for a bag of the Grizzles’ precious moon rocks. Cutler has reportedly signed off on the deal through his agent Bus Cook, and is apparently eager to show everyone in Denver how much stronger his arm is in space than John Elway.