KSK Story Time: That Time I Met Jay Cutler

08.15.14 3 years ago 37 Comments
via reddit


Yesterday, the KSK staff discovered that a disproportionate amount of us have met Bears QB Jay Cutler*. We thought that it might be fun to collect them all and share them with you. Keep in mind, these are all true**, actual*** accounts of us sports blogger types meeting an NFL quarterback****.

*none of us have met Jay Cutler
**these stories might not be true
***or actual

First, I’d like to tell my story.


I work at a bar on Tuesdays in Chicago, hosting trivia (it’s called Friar Tuck. Come see me sometime, and I’ll buy you a shot). Jay Cutler and Brandon Marshall came in and sat in the back. They were pretty personable, and signed autographs for the people who wanted them. Midway through the night, Jay took out a cigarette and started smoking in the bar. This is illegal in Chicago, and despite my Bears fandom, I had to go over to him and ask him to please either step outside to finish the cigarette or put it out. Cutler looked at Marshall, shrugged, and put the cigarette out on my forehead. Then, he walked out of the bar without paying for all the drinks he had ordered over the course of the night. Brandon Marshall ended up picking up his tab, and to his credit, did give us a pretty substantial tip.


One time, my wife of 11 years and I were at a bar in downtown Chicago one evening and, wouldn’t you know it, ol Jay Cutler himself saunters in with that Cavallari chick or whatever. He immediately makes eye contact with me and my wife, and I just about die. I mean, I love the Bears. I’m like, shaking as he walks up to our table. I open my mouth to say ‘Hi Jay how–‘ and he IMMEDIATELY put his hand in my face, and holds it there and starts talking to my wife. “Hey, wanna have sex right on this table right in front of your dipshit husband?” She said “Sure” and they went at it like a couple of rabid wolverines for 20 minutes while the whole bar watched. He finally took his hand out of my face, slapped Cavallari on the ass, and said ‘It’s time to go baby.’ To this day, my wife still yells out Jay Cutler’s name during sex.

Christmas Ape:

I saw Cutler next to a Bears fan choking in a bar while also wearing his jersey but he couldn’t care less. He sat there doing shots and telling stories about his best touchdown passes even though the other patrons were clearly more worried about the man choking. The man eventually died. When he left, Cutler grabbed the jersey off the body and said, “Hey, it’s mine. It has my name on it.”

Sarah Sprague:

I was heading into the Marc Jacobs store on Melrose when I saw Kristin Cavallari across the street heading into the other (fancier) Marc Jacobs store. Rolled my eyes, thought ‘fucking anti-vaxxer wackjob’ and went back to looking for a cross-body purse to replace the one that had broken when its strap got caught on my car’s gear shift over the weekend. My luck didn’t hold out long because about ten minutes later Wackjob showed up with surprisingly, Jay Cutler in tow. How had I not seen him before? Big guy, sort of hard to miss.

Of course now every sales person is over helping them and the rest of are totally screwed for help so I decide to just look at laptop cases worth more than my computer to kill time until they leave because Wackjob doesn’t appear to be seriously shopping, she’s just visiting the sales people to say, “HIIIIIII! HOW ARE YOU? OH MY GOD I HAVEN’T SEE YOU IN FOREVER. YOUR HAIR LOOKS GREAT. LOVE THE NEW CUT. YOU JUST LOOK SO RADIANT.” Of course the only sales people that treat me this way are the Gelson’s checkout cashiers, but whatever. I’ll take it.

Catler — it’s impossible for me to think of him as anything else thanks to this site — looks totally bored staring at the men’s section. Can’t blame him. Marc by Marc Jacobs for men is pretty Eurotrashtasic, even for bros like him. Wackjob on the other hand wants to play with her sales friends and Jay is about to be her Ken doll to play dress up with. A leopard print kangol-style hat. She holds up this orange-pink flowery hoodie to him. When she reaches for the rattlesnake skin baseball cap with the flat brim I have to choke back a laugh.

The entire store heard me. The stock boys in the back hear me and come out to see why the store is suddenly dead silent. My entire body is flush with embarrassment and I am frozen in place next to the sunglasses display case. I can by the look of fear in the sales clerk closest to me, I have to leave. Fast. The pleb with unbrushed hair, no makeup in a ten year-old Brooks Brothers blouse, torn jeans and flip-flops was no longer welcome. It felt like hours before my feet finally got the message from my brain that we had to move to the door and if we could possibly not trip on something like we usually do, that would be fucking great because if we do trip AND some one yells at me at same time TMZ is right outside to get it on all tape.

But of course I cannot help myself. I have to make an ass of myself in public because that’s what I do either inadvertently or advertently. I get to the exit, feeling every eye upon me and turn to push the door open with my hip. “DDDDOOOOOOOONNNNNNN’TTTTTTTT CAAAAAAAARRRRREEEE” leaves my mouth before I can stop myself and then run as fast as I can across the four lanes of Melrose not even looking if there is traffic and fling myself into the safety of the Diane von Furstenberg shop. Grab the nearest dress and stride into the changing room out of breath.

What it’s worth, I’m still looking for a replacement purse.

Trevor Risk:

Back in June, Cutler was in Vancouver because he lost a bet with Trestman. Something about how many Marlboro reds he could smoke in an hour. Anyway, Cutler lost and had to visit a Canadian city and watch a CFL game in its entirety, and Cutler chose the Lions because he heard Vancouver had ‘some top notch gash’. They just changed a few of the archaic liquor laws in my province, so now children can come into gastropubs during day time hours, as long as they don’t sit at the bar. Waiting for the game to start, the Cutlers and their children are all eating fish in this one bar, and for some reason we now have a rubella problem throughout all of Canada.

David Rappoccio:

I was stranded in Chicago one night due to inclement weather cancelling my flight. I made the most of it and hung out in some bars watching the Cubs lose. I stepped into the back to use the restroom at one point, and it was a big restroom with 5 urinals. I took the far one, alone in the room. Jay Cutler walks in and takes the one right next to me. He glances over at me and snorts. I decide to break the awkwardness by asking for an autograph, he proceeds to turn his body and writes “Jay C” on my pants leg in urine. He gives me a pat on the back “there ya go, buddy” and walks away without even zipping back up. At the door he stopped, looked down, and pulled a soggy box of smokes out of the trash can. He pulled out a lighter with a cartoon vagina on it, gave me one more snort, and left.

When I got back to the bar the girl I was chatting up was smoking a cigarette and said “Jay Cutler shared it with me”

Apparently, a few of our Kommenters have their own Cutler stories as well.

Beastmode Ate My Baby:

It was during the war that I knew Jay Cutler. Ruddy good chap he was, if a bit standoffish. While the other men were celebrating returning home from patrol with a song and a pint, he would be sitting by himself at a table. Sometimes he would be rolling a small ball back and forth, humming softly to himself.

Well, not a hum, really. More throaty than that, I’d say. More like a pur…

What’s that? Our last mission together? Crikey, that was a long time ago, but devil take me if I don’t remember it like it was yesterday. We’d had word that the Huns were on the move, so Jay and I took to our Sopwith Camels and patrolled the front. Wouldn’t you know it, we ran right into a full squadron of German planes, led by Goering himself! I thought we were buggered right then & there, but old Jay just flipped his Camel about in an Immelman and started firing away. One of the Fokkers split apart instantly, and Jay went after another, stalking it like a cat after a particularly fat mouse. That poor bugger didn’t last long either, and Goering, with a shriek I’ll never forget, turned about and fled back home to Jerryland. I was on the last Fokker, and doing a good job of it, I’ll have you know, when Jay came streaking down from above, Vickers guns chattering away as he made his third kill of the day. A bit gobsmacked, I was, and I don’t mind telling you!

Well, I gave old Jay a wave and started back toward the base when the blighter opened up on me! I thought the old man had gone right barmy! I twisted my plane left and right, but he stayed right on me.

“Jay,” I cried out. “We’re on the same side, old chap!”

As he closed on me, his machine guns were silent for a split second, and in that time I heard his voice clear as day. I still hear it sometimes, in my nightmares. Two words was all…two words that still wake me up shivering in fear.


Old School Zero:

I’ve never told this Jay Cutler story of mine before, but I just don’t want it to happen to anyone else.

Back when I was young, I really wanted to be a star. I heard about this acting gig that was supposedly a big payday that was always performed for the bigwigs in the industry. Well, I went to audition, and somehow I was the only one there. The guy in charge, this old guy, he asked if I could sing. So I sang him “I am the very model of a modern major general”, all the way through. He asked if I could act. I did all of Hamlets soliloquies. He asked if I could dance. I did this fantastic mix of dance styles to show my range.

Then he asked if I could suck a cock. I could tell he was serious.

I mean, it was the chance of a lifetime, right?

I showed him what I could do.

Then he asked if I could do other things.

And I did them. All of them. No matter what he requested.

I got the part. I went back home, bruised and at a new low, but knowing that I had a great future ahead of me, even at that cost.

A little while later, after learning the ins and outs of the show, it was time for the first performance. I had a full room, full of power players and stars. I was about a third of the way through, right into the felching-the-mime bit, when I catch this strong whiff of cigarette smoke and there’s this lackadaisical face in front of me, and after blowing smoke in my face, Jay Cutler looked into my eyes and screamed:


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