The inside story of how ‘(bleeping) idiot’ Darren Rovell, in search of a quarter-million dollar payday, cashed in on the bet of his life

There was a moment Saturday when I wondered if Darren Rovell had a wastebasket nearby. The man looked ill, as if he’d just ridden Space Mountain after downing a bowl of clam chowder.

He was at a loss for words for the first time in his 42 years.

Rovell had declined a buyout of $71,835 on his Northwestern Futures bet. He’d gotten a little greedy, perhaps. With Northwestern leading 10-6 and getting the ball to start the second half, he left that bounty on the table. The decision looked wise as Northwestern drove to the Ohio State 9. But then Peyton Ramsey threw an interception.

The Buckeyes were driving – 13 yards for Trey Sermon. Then 12 yards for Sermon. The offer was evaporating.

Dozens of people messaged with sentiments like: You dope! You should have taken the money.

But then Ohio State’s Justin Fields threw a pick. Rovell could breathe again, at least enough to say: That’s it. I accept the offer.

And that’s how Rovell, the Action Network executive with 2 million Twitter followers, got $67,831 richer.

Before we continue, some background: Rovell is the kind of guy who got the most wedgies in his school and then, 30 years later, purchased the school.

“I’m honored to be a nerd,” he tweeted in September. “Nerds win in life.”

Rovell attended Northwestern and loves his alma mater more than you love hitting a six-team parlay. PointsBet sponsors Fade Rovell, a segment in which the public is encouraged to bet against his picks. When he loses, Rovell must complete a punishment.

Recently I suggested that a penance would be having to miss a stretch of a Northwestern game. He nixed that. Instead Rovell agreed to eat dog food in an ode to the Cleveland Browns’ dog pound.

Yes, he’d rather eat puppy chow than a miss a minute of his Cats. Sick man.

After Northwestern opened the season 2-0, Rovell texted me a screenshot of some intriguing betting slips. The first was a $300 wager on Northwestern to win the Big Ten at +20000. Payout: $60,300.

Next bet: $200, at the same odds. Payout: $40,200. Three more at those odds. Then our traders lowered them to +15000. Rovell kept betting until they fell to +6600 … i.e. 66-to-1.

In the end, he stood to make $238,000.

I texted: “You beast. Maybe OSU has a covid outbreak before Indy.”

The Wildcats kept winning, clinching the Big Ten West in late November. PointsBet offered to buy out his tickets for $17,500, more than 10x his $1,550 investment.

Would he accept? Nope.

“It’s bad karma,” he texted.

Oh, he’s one of those guys.

Rovell, who practically invented the sports business beat, hatched this idea: What if he appeared on a livestream during the Dec. 19 Big Ten title game with a co-host from PointsBet and a banker offering him suitcases full of cash. Deal or No Deal?

I was drafted to play the role of Howie Mandell.

“We are a go,” Rovell texted me Dec. 13. “Announcing tomorrow.”

Rovell was a jumble of nerves midweek after hearing rumors of an actual COVID-19 outbreak at the Woody Hayes Center. Would the Big Ten replace Ohio State with an inferior opponent, driving up the value of his tickets? Or would the conference cancel the game, rendering it a no-contest that could result in a $1,550 refund?

With key Ohio State starters such as receiver Chris Olave sidelined, PointsBet increased its offer before kickoff to $28,370.

No deal.

“We are not cashing out,” Rovell texted. “We are riding.”

Rovell took a seat in his mancave, which is more like a Northwestern fan cave. Jerseys hang of NU legends such as Corey Wootton (the last man to sack Brett Favre), Dan Persa (career 72.7 completion percentage) and Darnell Autry, who finished fourth in 1995 Heisman Trophy voting.

I opened our livestream by saying I’ve known Rovell for a long time but I never knew he had brass balls.

The hope was that Northwestern would take an early lead, which would prompt PointsBets, which live-traded his Futures bet, to boost its offer.

Would you believe that Northwestern, a three-touchdown underdog before the COVID news hit, drove 75 yards on its first possession? The buyout surged to $52,190.

Could he hedge by selling off a slice? Maybe take 50% ($26,095) with a shot to earn another $119,000? Nope. PointsBet said that would not be possible once the game started.

With Northwestern ahead 10-3 late in the second quarter, I asked PointsBet communications chief Pat Eichner for an updated offer. His response, relayed from our traders: $64,235.

Rovell provided Twitter updates, and thousands of people checked out the telecast. Make that hundreds of thousands – 337,108 live viewers and 119,139 on replay.

Action network content director Chad Millman and senior writer Collin Wilson joined the telecast to offer their two cents. As did Rovell’s mother, Marcia, who recommended Darren use his head.

Rovell also took guidance from a seemingly endless stream of financial advisers – the names growing in absurdity each time. Rex Mogul says I should make a deal, but Hugo Yachtinton recommends I let it ride.

This felt even more live than live TV. At one point a female voice could be heard calling someone a “f**king idiot.” That voice belonged to his wife, Cortney Rovell. And the someone was Darren, who left the car door open overnight in their New Jersey garage.

Finally after NU’s Cameron Mitchell secured a third-quarter interception with a sideline tap dance, Rovell declared he had seen enough. Make the deal, he told me.

I informed Eichner.

With the Northwestern moneyline at +190 (implied victory odds of 34.5%), the final tally was $67,831.

As I told Rovell, instead of buying a lightbulb for the car, he could purchase a new BMW.

Rovell’s timing proved prescient. NU’s final six possessions resulted in a punt, missed field goal, interception, fumble, punt and turnover on downs.

Final score: Ohio State 22, Northwestern 10.

Had Rovell let it all ride, he would have lost everything. Instead he fell just $4,004 short of PointsBet’s top offer. He also made $1,000 by betting on the Wildcats +19.5.

Not bad, I told Rovell, for a f**king idiot.

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