Dear Readers,

The coronavirus pandemic has caused widespread disruption to the lives of everyone in Tampa Bay and to so many businesses in our community. Here at the Tampa Bay Times, we continue to provide free, up-to-date information at as a public service. But we need your help. Please consider supporting us by subscribing or donating, and by sharing our work. Thank you.

  1. Sports
  2. /
  3. Bucs

Will this professional bettor cash in on Tom Brady to the Bucs?

Mark DeRosa, who once won $286K on Lamar Jackson for MVP, may face a hiccup with his pay day if the coronavirus pandemic impedes the start of the NFL season.
A little more than a month ago, Tom Brady to the Tampa Bay Buccaneers may have seemed like a long shot. [CHARLES KRUPA | Associated Press]

It was the morning after Super Bowl 54 when Mark DeRosa played the odds.

The South Florida resident makes his living betting on sports, offering educated guesses when it comes to all kinds of teams and using the futures market for leagues he is not as tuned into.

DeRosa was already in Atlantic City, and his flight back home to Florida wasn’t until the afternoon of Feb. 3. He had some time to kill, so he visited a couple of casinos.

He found a DraftKings sportsbook at one resort and hedged a proposition bet on Tom Brady playing for the Buccaneers in Week 1 of the 2020-21 NFL season. He put in two separate $500 cash bets on the six-time Super Bowl champion heading to Tampa Bay for a $45,000 profit.

And on Friday, his hunch paid off — well, maybe — when Brady inked his contract with the Buccaneers. With the current coronavirus pandemic creating a lot of uncertainty on the scheduling front throughout professional sports, it’s possible DeRosa won’t see his big pay day.

DeRosa knew his chances of winning were better than just okay. His 16-year track record of betting on the NFL proves it. He previously won $286,000 for predicting Lamar Jackson for MVP in 2019; that was his biggest win on a single event to date.

The 37-year-old, who lives an hour outside of West Palm Beach, could have bet Brady would go to any team, but the Buccaneers had the best value (50-1 odds when he placed his first bet at 10:20 a.m. and 40-1 odds when he placed his second eight minutes later). He bet the $500 limit both times.

“Why would you want to bet on (Brady) to the Bucs?” the cashier asked DeRosa after his second trip to the counter. “Do you know something we don’t?”

Related: Bucs re-sign defensive tackle Ndamukong Suh for one year, $8 million

DeRosa’s rationale was clear. The Patriots had been eliminated by the Titans in the wild-card round and he had seen articles about a rift between Brady, New England’s ownership and coach Bill Belichick. Brady putting his house up for sale last August swayed him even more.

“I was very intrigued by the story and the possibility of him leaving (the Patriots),” DeRosa said. “To me it seemed like he had one foot out the door when he (put his house up for sale).”

DeRosa also knew Brady was dealing with a limited market, only five or six teams would really be interested in him (and could afford him), and he thought the Buccaneers were his best fit.

Related: Could the Bucs’ classic creamsicle uniforms make a return? Bruce Arians says yes.

“I felt like (the Bucs) were tired of Jameis Winston. They’d given him five years and what you see is what you get after five years,” DeRosa quipped. “You don’t see many quarterbacks make a change after that.”

DeRosa thinks the Buccaneers could be really good this year, too, especially with a quarterback who turns the ball over far less.

At the end of February (way before Brady signed his contract with Tampa Bay), DeRosa placed an additional two bets: $10,000 on the Bucs winning the NFC South and $8,000 on the Bucs winning the NFC. If both of those things happen this season, he’ll net $360,000.

“You put in somebody like Brady who doesn’t throw (interceptions) very often, I think they’re going to be extremely good next year,” DeRosa said. “If there is a next year.”

The impact of the coronavirus on the sports world has shaken up the betting world, too. DeRosa said that while his gamble was right, he may not cash in if the NFL doesn’t play this season or if the season is somehow truncated. The wording on his two tickets reads: “Tom Brady’s team for Week 1 of the 2020 NFL regular season: TB Buccaneers.”

“I have no idea what’s going to happen,” he said. “It’s really unfortunate. I’ve been doing this for 16 years and I’ve never come close to a situation like this, where you’ve won the money but there’s a 50 percent chance you’re not going to get paid.”

But even if DeRosa could predict the future, he likely still would have been all in on Brady. “Even if I knew there was a chance the season could be postponed,” he said, “I’d probably still make the bet because it was just a really good value.”

Contact Mari Faiello at Follow @faiello_mari.