Dealing with Spygate, Deflategate, the Ray Rice investigation, and Colin Kaepernick-inspired protests were all child’s play compared to what NFL commissioner Roger Goodell will have to deal with during a Monday Night Football game this fall.

What he’s facing is bad enough that you have to wonder whether Goodell wouldn’t mind having the 2020 season wiped out by concerns over the coronavirus pandemic.

A night in Roger Goodell’s basement man cave was up for bids

Commissioner Roger Goodell and the NFL had the great idea to stage an auction in conjunction with the NFL draft last month. The contributions were earmarked to help combat the effects of COVID-19. Raising money for a worthy cause was both the right thing to do and a way of taking some of the heat off the league for going about business as usual while much of the country was locked down during the pandemic.

Well, the expression about no good deed going unpunished came into play with one of the auction items: the chance to watch a Monday Night Football game with Goodell in his man cave featured prominently when he hosted the draft.

The good news was that the winning bid brought in enormous money for the COVID-19 fundraiser. The bad news for Goodell was that the bid was placed by Dave Portnoy, the founder of Barstool Sports.

Barstool Sports’ Dave Portnoy is more than just an NFL critic

Barstool Sports is a polarizing entity in the no-holds-barred world of modern media, although founder Dave Portnoy has offset some of the criticism by digging deep into his own bank account to help important causes.

Last fall, a Barstool Sports personality started a drive to raise money for Headstrong, which provides services to veterans dealing with trauma. Portnoy saw what was going on and announced that he would match whatever amount was donated.

Whether their motivation was to help a worthy charity or to hit Portnoy in the wallet, donors stepped up to the tune of $91,000. Joking that he felt like he’d been sandbagged because he only expected $10,000 to be raised, Portnoy nevertheless pledged $91,000 of his own money.

However, the NFL draft auction took Portnoy’s generosity to a whole new level. He paid $250,450 for the right to watch a football game at Roger Goodell’s home in New York City’s northern suburbs.

NFL commissioner Roger Goodell is in for a long night

Dave Portnoy doesn’t hide his disdain for Roger Goodell, so the NFL commissioner probably already has some misgivings about having to follow through on the auction prize.

Portnoy’s Massachusetts roots show through in his animosity toward Goodell. In 2015, he was arrested during a protest at the NFL offices after Goodell suspended New England Patriots quarterback Tom Brady for four games over the Deflategate scandal. He followed that by creating towels and shirts portraying Goodell with a clown nose.

Portnoy was also kicked out of a Super Bowl LII media event that he crashed, then removed from the championship game in handcuffs that weekend after being banned from NFL events.

One Monday night this fall figures to be Portnoy’s revenge.

“We got all day,” Portnoy said in a video gloating over his auction win. “Football takes what, three, four hours? No handcuffs, no jail. I won fair and square. Let’s put that money to good use.”