Professional gambler Mark DeRosa was on a plane back from Atlantic City after last year’s Super Bowl when he got a clear idea of what would turn out to be one of the biggest scores of his career.
DeRosa believed that Tom Brady would be leaving New England off-season and that Tampa Bay was one of the most likely landing spots. Sportsbooks disagreed, however, scoring the Buccaneers around 50-1 in their odds of where Brady would play in the 2020 season. Bookmakers made Brady returning to New England a firm favorite.
“The books praised it as if it was a 75% chance that he will return [to New England]”Said DeRosa.” I thought there was a 75% chance that it wouldn’t return, so the market was really far away. “
While in Atlantic City for the Super Bowl, DeRosa placed two $ 500 bets at DraftKings on Brady playing with the Buccaneers at 50-1 and 40-1. Then, on the plane back to Florida, he decided he wanted to go to Tampa Bay more to win the NFC and Super Bowl the following season. He would have to convince his old college buddy and gambling partner Zack White that the Bucs were a good bet.
Tampa Bay had just finished a 7-9 campaign in which quarterback Jameis Winston threw 30 interceptions. It was the Buccaneers’ third consecutive losing season and they were again considered long shots, with a Super Bowl chance of 65-1.
“He had to talk to me about it quite a bit,” recalls White, a respected Las Vegas gambler. “His reasoning pretty much boiled down to Brady going there.”
White asked DeRosa what he thought were the odds of Brady landing in Tampa Bay, “because if he doesn’t, then this bet is pretty awful.”
DeRosa said he had a suspicion, a well-reasoned suspicion based on several signs suggesting that Brady was leaving New England. DeRosa recalled a 2018 ESPN story highlighting the rift between Brady, Patriots coach Bill Belichick and owner Robert Kraft. In August 2019, DeRosa read that Brady had put his Massachusetts mansion up for sale, and he felt it made sense that the six-time Super Bowl champion quarterback had his contract expire for the first time in his career.
DeRosa believed that Tampa Bay – due to coach Bruce Arians’ displeasure with the revenue-sensitive Winston, a roster full of playmakers, hot weather and lack of income taxes – was one of the few bouts for Brady.
“The worst scenario is that you have it [Tampa Bay] 30-1 to win the NFC and 60-1 for the Super Bowl, and that’s just the market price, “DeRosa reasoned with White last February.” When it happens, they’ll be like 5-1 and 10-1. , and I really think it’s going to happen. I don’t think he will come back. I think he’s going elsewhere. “
Convinced, White went to work in Las Vegas, where he placed several thousand dollars on the Buccaneers to win the Super Bowl 65-1 and 60-1. Meanwhile, back in Florida, DeRosa had been keeping an eye on the odds at New Jersey sportsbooks and saw the Borgata open the Bucs at 35-1 to win the NFC. DeRosa immediately booked a flight back to Atlantic City and placed an $ 8,000 bet on Tampa Bay to win the conference 35-1.
When DeRosa and White finished betting, they had invested about $ 20,000 in the Bucs at odds of around 65-1 to win the Super Bowl and 35-1 to win the NFC. They each took smaller positions in a few teams, DeRosa on the Los Angeles Chargers and White on the Saints, but their biggest investment went to the Bucs.
On March 20, Brady signed a two-year deal with the Buccaneers, whose Super Bowl odds improved dramatically at sportsbooks. When the season got underway, Tampa Bay was around 10-1 to win the Super Bowl and 5-1 to win the NFC, just as DeRosa expected.
Things didn’t look great for the Bucs mid-season. They lost three of the four in November, including a 38-3 loss against the Saints, only to fall back to 7-5.
“There was a bit of frustration,” White said, chuckling at the mid-season swoon in Tampa Bay, “but it’s the NFL, man, you don’t count anyone until the end.
“There was always so much value in those big tickets,” White added. “You could have made a lot of profit before the season even started with the numbers we had.”
They each covered a small portion of their risk by taking the Washington Football Team +9.5 in the division round of the playoffs against the Buccaneers. Tampa Bay won with eight. But for the most part, they held on tight and planned to do the same for the Super Bowl. The Buccaneers are 3-point underdogs to the Kansas City Chiefs.
“I’m not much into hedging,” DeRosa said.
DeRosa and White were both in their late 30s and attended Appalachian State together and have been betting professionally for over a decade. They’ve already earned a six-figure win on the Bucs and are in position for their career’s greatest scores in any sport if Tampa Bay wins the Super Bowl.
“We had about $ 11,000 or so to win $ 400,000 in the NFC Championship,” said DeRosa. “And then we have another $ 8,000 or $ 9,000 to win the Super Bowl 60-1.
“So, go Bucs.”