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Come Fan with UsThursday, August 6, 2026

NFL Playoffs: Should We Be Rooting Against Jay Cutler, Or Rick Reilly?

With the Chicago Bears back in the spotlight for the first time in a few years, there's been plenty of attention on Jay Cutler this season. But look closer, and as ESPN's Rick Reilly wrote at ESPN this week, Cutler is one of the least likable players in the NFL.

This guy’s not likable? GET OUTTA TOWN.

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On the other hand, a Bears writer offers a counterpoint: Rick Reilly is just angry that Cutler wouldn’t give him an interview, and his latest column reeks of pettiness and wounded pride. After the jump, we’ll break this down.

First, the lede from Reilly’s column in his inimitable, vaguely infuriating style:

For a man from Santa Claus, Ind., Jay Cutler is one of the least jolly people you’ve ever met.

If he’s not The Most Hated Man in the NFL, he’s in the running. His expression is usually that of a man wearing sandpaper underwear. He looks everywhere but into your eyes. It’s a tie as to which he enjoys more -- smirking or shrugging.

Reilly proceeds to relate a series of anecdotes from Cutler’s time in Denver, painting Cutler as selfish, unfriendly, and arrogant beyond his years. It culminates like so:

Then there was this:

Reporter: When you were a kid, which quarterback did you look up to?

Cutler: Nobody.

Reporter: Nobody? You didn’t look up to anybody?

Cutler: No.

If he’s lying, it makes him a miscreant. If he’s telling the truth, it makes him a miscreant.

Ugh. He wouldn’t talk to the media about his childhood heroes? WHAT A MISCREANT.

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On the other the hand, Bob LeGere of Chicago’s Daily Herald provides some context here:

Maybe Reilly was just salty because, after he had invested three hours of his time at Halas Hall, Cutler declined to bare his soul, get in touch with his inner child or explain in detail what it is that makes him tick.

Imagine the gall of Cutler not to genuflect and share with Reilly his innermost thoughts the moment he saw him. What was Cutler thinking? How could he be so arrogant? I mean, this was THE Rick Reilly. How could he dare not answer HIS questions.

... Does Cutler come off as arrogant and disinterested during press conferences? Absolutely. Does he have any use for the media? Doubtful. Does he fail to look people in the eyes when he’s talking? Sometimes, maybe a lot of the time, but he’s getting better.

See, this one feels like one of those unfortunate pot-kettle incidents where both sides are wrong. Let’s see... Jay Cutler has always seemed like a smug, entitled, lazy pile of mediocrity. But that’s just how he seems. To me. I mean, I can point to the magazine cover above as evidence that Cutler’s a smug, insufferable douche, but even that doesn’t count as proof.

And what Rick Reilly’s trying to do is prove--in an objective, journalistic way--that because he doesn’t publicize his charity work and refuses to name his childhood heroes, Cutler is some combination of Scrooge, Jeff George, and “a man wearing sandpaper underwear.” So, yeah.

As insufferable as Cutler might seem, I'm pretty sure Rick Reilly just proved he's even worse.

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