Roger Goodell and Dave Portnoy hanging out in the NFL commissioner’s basement, watching Monday Night Football?

It could happen. Really, it should happen under the circumstances of what’s become a more bizarre situation than anyone other than the founder of Barstool Sports likely imagined.

During NFL Draft weekend, the league also held a Draft-A-Thon with a variety of auctions to raise money for COVID-19 relief. One of the items up for bid was an opportunity to watch an MNF game with Goodell in his basement “man cave” that served as the commissioner’s base of operations, along with two tickets to any regular-season NFL game. And the top bidder for this particular item was indeed the man behind Barstool Sports, who screen-capped the official email to show this was reality.

Portnoy, an outspoken critic of Goodell, put up $250,000 (from an opening bid of $50.00) for the opportunity to watch MNF with the Commish. So the question now becomes whether or not Goodell will follow through on the promise of the prize and hang out with Portnoy for three, maybe four hours some night this fall. (That is, of course, if a 2020 NFL season is played. If not, the get-together will presumably happen during a future season.)

Wearing the t-shirt bearing an image of Goodell sporting a clown nose that Barstool made iconic (and worn by NFL coaches such as Matt Patricia and Sean Payton), Portnoy held one of his signature emergency press conferences to announce that he’d won the NFL auction. Just to put a finer point on the matter, Portnoy also wore a “Fire Goodell” hat during the video.

“Two hundred and fifty grand. A quarter Milly. That’s how much it cost me,” said Portnoy in his announcement. “Good charity. Great charity. I’m happy to give the money. Let’s fucking help people. Let’s go watch some football, Roger.”I got some questions. We got all day. Football takes, what, three, four hours? No handcuffs, no jail. I paid fair and square. I won. Quarter Milly. Me and you, Roger. Let’s put that money to good use. You know, I’m happy to donate it. Let’s talk.”

If you’re unfamiliar, Portnoy’s “No handcuffs, no jail” comment refers to two separate incidents in which the Barstool Sports founder was arrested for confronting Goodell indirectly. In 2015, Portnoy was among a group of Barstool fans arrested for protesting the suspension of then-New England Patriots quarterback Tom Brady outside of NFL headquarters in New York. He was subsequently banned from NFL events. Because of that, Portnoy was kicked out of a Super Bowl LII media event and later removed from his seats at the game in Atlanta and taken away in handcuffs.

Putting aside that this may be a nightmare scenario for Goodell, Portnoy is right. If this is legitimate, and there’s no reason to think that it isn’t, he participated fairly in the auction and put up the winning bid. He should be able to watch football with Goodell in his basement.

Can Goodell really turn this down and risk the embarrassment of Portnoy causing an uproar and possibly threatening to take $250,000 away from charity? Sure, it could be an embarrassing situation for Goodell either way — especially if Portnoy wears a Go Pro camera during the entire get-together, as he says he will — but doesn’t he look worse if he somehow reneges on the terms of this agreement? (Unless there is some kind of language in the rules that gives Goodell an out. Even if so, Portnoy seems likely to pay whatever it might take to fight that, if he was willing to go to seven figures on an auction bid.)

Regardless of what you think of Barstool Sports, this is a potentially hilarious situation virtually guaranteed to make one of the most powerful men in professional sports squirm. Whatever photos and video come from Goodell and Portnoy meeting will be memorable.[CBS Boston]

About Ian Casselberry

Ian is a writer, editor, and podcaster. You can find his work at Awful Announcing and The Comeback. He's written for Sports Illustrated, Yahoo Sports, MLive, Bleacher Report, and SB Nation.