Dave Portnoy cashes in $2 16 million UConn March Madness win

Back in 1998, Richard Hopkins and his son went go-kart racing just for fun, and Richard couldn’t help but notice Lewis Hamilton driving around the course. Richard was so impressed with Hamilton’s skills that he went on to spend several hundred pounds betting on him. The punters placed a high-risk bet on horse racing known as a superfecta. For the uninitiated, a superfecta is a type of wager where you’re to predict the first four horses that’ll finish the race in the exact order that they come in.

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It took until the second half, but Hill ultimately delivered for bettors, hauling in an 80-yard TD reception in the third quarter to instantly cash both props. His final receiving yards tally was also enough to cover most alternate lines. “It was significant,” Craig Mucklow, vice president of trading at Caesars Sportsbook, said of the Patriots pulling off the upset. “Obviously, you get the biggest favorite on the board beat straight up in Week 1, that’s a good start for the book.” The jump was easily the biggest of any team in the league and the Padres now have the eighth-best odds in baseball to win it all.

Full list of all-time biggest betting wins

Hamlin hasn’t finished higher than 17th over the last eight Daytona races. But we think that’s far more likely to be Daytona noise than a skill regression. Joey Logano (+1200)Logano is going to be at the front of the field at some point.

• BigiBet is considered to be one of the most famous bookmakers in Nigeria.
• On Nov. 29, 2019, the NFL suspended then-injured Arizona Cardinals cornerback Josh Shaw for betting on NFL games on multiple occasions.
• The Huskies and Bruins account for over 50% of the national championship handle at BetMGM, but the Gamecocks, with their slightly longer accounts, are actually the sportsbook’s largest ticket holder.
• According to the National Conference of State Legislatures, most states tax sports gambling at between 5% and 20%.
• The Huskies rolled through their competition, hardly being threatened en route to their back-to-back national championships.
• Although Tiger Woods is one of the most famous professional golfers in the world, betting on him hasn’t always seemed like the smartest choice.
• Caesars also said it was the first Super Bowl in which more game parlays were bet than the more traditional straight wagers.
• That said, despite the perceived chalkiness of the women’s game, odds-on lines are not an automatic indicator of success.
• Whether it was a self-fulfilling prophecy or a stroke of good luck, we’ll never know.
• When you click on a certain kind of sport to place a bet on, you will see what events are accessible.
• Zarb-Cousin successfully lobbied for stricter gambling regulations in Britain—limiting how betting companies advertise and how much gamblers can wager.
• Some form of sports gambling is legal and regulated in 38 states, as well as Washington, D.C., and Puerto Rico.
• That said, 1-seeds Arizona, Michigan and Florida have also been named as liabilities with the major books, providing some futures variety, even if just within the top nine teams.

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However, due to the nature of baseball scores and how close teams tend to be to each other, betting the favorite on the run line often comes with plus-odds, while the underdog on the run line comes with minus-odds. Some of those betting could back top underdogs and see huge payouts like one that happened on Friday night. Fairleigh Dickinson, a small school in New Jersey, defeated one of the top teams in college basketball Friday night. An anonymous 25-year-old was bored waiting for his basketball game to start, so he headed to the Excalibur casino to pass the time.

• The anonymous bettor only paid the $5 participation fee at one of the top betting sites William Hill sportsbook but successfully took home $305,375 after correctly selecting 12 winners in one weekend.
• But we think that’s far more likely to be Daytona noise than a skill regression.
• The buy-in for each betting event ranges from $0 to $1 each, reflecting a 0% to 100% chance of what users think could happen.
• Former Jacksonville Jaguars employee Amit Patel, who stole $22 million from the team, was sentenced to 6 1/2 years in prison on March 12, 2024.
• Though Ohtani has looked dominant in his own right, having not yet allowed a run in two starts, the Dodgers look to keep him fresh for the full 162-game stretch.
• Ten days after the MLB announced the Marcano ban, the league said it disciplined umpire Pat Hoberg for violating the league’s gambling rules.
• He got not one, but two of the biggest sports betting wins in a matter of weeks.
• Unsurprisingly, the odds of making such an accurate prediction are minuscule, about 88/1.
• Football, basketball, ice hockey, and tennis are the options picked most frequently.
• He first placed a $250 wager on the St. Louis Cardinals winning the National League.

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But this game is remembered for Panthers WR Xavier Leggette letting a would-be 32-yard TD pass in the end zone go through his hands with under a minute remaining. The Eagles eventually turned the Panthers over on downs and won 22-16, but this bettor probably sweated profusely through the game. When you click on a certain kind of sport to place a bet on, you will see what events are accessible. You may choose a specific date and explore what matches are the upcoming ones.

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However, even Packer couldn’t sustain his winning streak for too long. By 1999, his gambling hobby had cost him about $28 million in London. Instead of taking all of the money at once, he made a deal with the casino to receive $1.5 million annually over the following 25 years. Although Tiger Woods is one of the most famous professional golfers in the world, betting on him hasn’t always seemed like the smartest choice.

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However, he hasn’t won since he took the checkered flag in the 2015 Daytona 500. As you can probably surmise from the bunched-up leaderboard, the oddsboard is a bettor’s delight. And then it’s Augusta specialists Justin Rose and Jason Day at 8-under. Right behind them at 7-under is some guy named Scottie Scheffler and Haotong Li. To learn more about the terms for our sportsbook and casino please see our Terms of Use.

That said, 1-seeds Arizona, Michigan and Florida have also been named as liabilities with the major books, providing some futures variety, even if just within the top nine teams. The chalk will be the main topic of conversation as the men’s NCAA basketball tournament gets underway. “This has been a tale of two halves for the year,” Berbert told ESPN. But overall, the divide between the power conferences and everyone else appears to be growing. Denny Hamlin (+1400) Hamlin’s odds are so long despite being a three-time Daytona 500 champion because his recent stats stink.

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Soon after, he got arrested in England for one of his notorious schemes. After serving eight years for fraud, and getting arrested a couple more times afterward, Charles Wells died without a penny to his name. It all started when he ripped off £400 from his investors, claiming that he was inventing a musical jump rope. Instead, he set off for Monte Carlo and tried his luck at roulette. Amazingly, the stunt paid off, but his luck would quickly run out. Spending some quality time with your children pays off in more ways than one.

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Heading into the Wild Card game, the Eagles were also missing leading wide receiver A.J. Brown, who led the team with 106 receptions, 1,456 receiving bigibet yards and 158 targets. Brown’s seven receiving touchdowns were tied for the lead on the team. The collapse by the Eagles heading into the postseason could be the reason for the bet. The Eagles fan bet on their favorite team to lose the opening round of the NFL Playoffs to the Tampa Bay Buccaneers. Instead of accepting her full prize in 30 monthly instalments, Gloria decided to cash in her prize immediately, so she received only half of the money (still more than enough for any single person).

Bipartisan groups of senators as well as representatives have introduced legislation that would broaden the definition of insider trading to include prediction markets. While some users took handsome profits, others must wait for payouts because Polymarket has labeled the April 7 Iran-U.S. Ceasefire contract as “disputed,” given that Iran was still placing restrictions on ships passing through the Strait of Hormuz and missile attacks in the region continued. Rory McIlroy and Cameron Young are the co-leaders at 11-under par after three rounds, but there are six golfers within four shots of the pace-setters.

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• When the line was reposted, with Love ruled out with a sprained MCL and backup Malik Willis expected to start, the Colts were 3-point favorites.
• November of 2015 was an astonishingly lucky month for Dave Oancea, nicknamed Vegas Dave.
• The Knights had to win a play-in game between 16-seeds earlier in the week to make it into the field of 64.
• Barkley’s rushing total was set at 110.5 yards, and he finished with 57.
• His attorney previously said the vast majority of the $22 million he stole was to subsidize gambling losses.
• He didn’t race in Wednesday’s Clash, but plans to be medically cleared for the Daytona 500.
• In 1996, he placed a £62 bet on Frankie Dettori to win all seven of his races for the day.
• He took on the odds of 1,666,666/1 and placed a mere £0.30 on a 15-leg parlay on the Champions League games.
• Nicholas Newlife would be proud to have one of the biggest sports betting wins in history.

Not many St. Louis Cardinals fans would have placed $500 on them before the 2011 MLB season, but that’s exactly what this anonymous bettor did. He first placed a $250 wager on the St. Louis Cardinals winning the National League. Then, he placed another $250 wager on the team coming out victorious in the World Series. Eventually, the St. Louis Cardinals came out on top, and the bettor received accumulated winnings of $375,000  (approximately £286, 000).

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“Everyone’s writing off the Patriots, including us,” Mucklow told ESPN on Sunday. The Chiefs have reached the Super Bowl in five of the past six seasons, taking home the Lombardi Trophy three times during that stretch. The Padres were the biggest winner of the MLB trade deadline in the eyes of oddsmakers. Out of more than 20 million brackets in the Tournament Challenge, none remain perfect.

For this article, though, we’re focusing on the largest reported winning wagers in U.S. sports betting history — all of which have happened since 2018. And wouldn’t you know it, the largest of all comes from just a few months ago from a BetMGM bettor in Ohio who wagered $8 million on the Oklahoma City Thunder to win the 2025 NBA Finals over the Indiana Pacers at -700 odds. Last but certainly not least, among the biggest betting wins in history is Gloria McKenzie and her Powerball pay-off. In 2013, 84-year-old Gloria achieved the highest single winning record in Powerball history and took home $590.5 million, beating the odds of 175 million/1.

Back in 1891, Wells broke the bank at Monte Carlo and collected a million Francs (over $500,000 in today’s market) after an 11-hour marathon of roulette. Gerry ended up winning £100,000, and his friends who had the same faith in Rory won £80,000. With millions of people around the world testing their luck daily, someone’s always bound to hit it big. “Certainly, prop bets, depending on how precise they are, lend themselves to more shenanigans than other kinds of bets,” NBA Commissioner Adam Silver said in May.

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• Another item working against the Eagles was the team being the favorite in the game despite being the fifth seed.
• St. John’s buzzer-beating layup gave christienter the win and the ESPN record at 43-0 to start the tournament.
• New customers can benefit from our welcome offer while existing players can enjoy loyalty rewards on Bundesliga fixtures throughout the season.
• Previously, those wagers could (legally) be made only in Nevada, and speaking with many veteran Vegas bookmakers for this story, there certainly were plenty of seven-figure wagers made before legalization.
• The Texas Legislature meets every two years and will be back in session in 2025, but so far it hasn’t seemed to have an appetite for getting into sports gambling.
• During the football season he’s showcased massive profits at The Post in the player prop market the last two seasons.
• Cynthia Jay-Brennan sat down at the Megabucks Slot Machine during her mother-in-law’s birthday party in 2000.
• In 2024, Byron took the lead for the first time on a late restart and led the final four laps.
• The opportunities for action are, literally, limitless… live in-game microbetting–allows users to wager on every pitch, serve, and snap.
• Along those lines, the first-round spreads have been benefiting the top seeds in a noticeable way.
• Everything that happens in sports has additional context when viewed from a betting perspective.

The following examples show just how well taking risks can pay off. The Texas Legislature meets every two years and will be back in session in 2025, but so far it hasn’t seemed to have an appetite for getting into sports gambling. While Texas has been a state generally opposed to all forms of gambling, the biggest barrier currently is Republican Lt. Gov. Dan Patrick, who has great influence over what bills are put up for a vote. He isn’t sold that the tax benefits, that he’s previously said would pay for about half a day of Texas’ yearly budget, are worth it.

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Despite the opening upset, expectations for the Patriots remain low. Patrick Mahomes and the Kansas City Chiefs are headed to the big game once again and will aim to become the first team to capture three straight Super Bowl titles. Standing in the way of history will be Saquon Barkley and the Philadelphia Eagles, making their fifth Super Bowl appearance overall and second in three years.

• The two largest sportsbooks in the U.S., —DraftKings and FanDuel—said the same… though declined to provide specific instances when they’ve done so.
• John opened his betway account in 2015, joined the Mega Moolah, and won the record-breaking €17.8 million (about $21.2 million) in less than half an hour.
• However, there’s no evidence to say a point spread bet is riskier than any other sports bet.
• On June 4, 2024, MLB announced a lifetime ban against then-injured San Diego Padres player Tucupita Marcano after the league found he had placed 25 bets the season prior on the Pittsburgh Pirates as a member of that team.
• The punters placed a high-risk bet on horse racing known as a superfecta.
• The Eagles eventually turned the Panthers over on downs and won 22-16, but this bettor probably sweated profusely through the game.
• Tomlin turned to Justin Fields for the start, which shifted the line on the Steelers from +3.5 to +4 or +4.5, depending on the sportsbook.

But tax revenues have varied vastly because only 15 states collect at least 10% of every dollar wagered. Argentina captain Lionel Messi — considered by many the greatest player in the history of the game — hasn’t said with absolute certainty that he’ll play in the World Cup. Then-New York Jets wide receivers coach Miles Austin was suspended for violating the NFL’s Gambling Policy, a league source confirmed on Dec. 23, 2022. There was no indication that Austin bet on NFL games as a coach, but bet on other sports in violation of the league’s policy. In light of the recent news, let’s revisit the famous sports betting scandals since that landmark case. Caesars also said it was the first Super Bowl in which more game parlays were bet than the more traditional straight wagers.

He chose his horses very carefully but didn’t believe much would come out of it. Phil Mickelson, a professional golfer, became quite a fan of the Baltimore Ravens even before they made it big in 2000. Seeing the team’s strength and talent after a good season, Phil made a betting syndicate and placed a $20,000 bet against the odds.

His lawyer later said the ex-Detroit Pistons guard, now a free agent, was not a target of the Department of Justice’s investigation into sports gambling by players. The NBA opened its own investigation into Beasley over the summer. New England Patriots wide receiver and former LSU player Kayshon Boutte was arrested in January 2024 and charged with computer fraud and gaming prohibited for persons under 21, Louisiana State Police previously announced. Boutte participated in sports gambling from April 6, 2022, until May 7, 2023, when he was 20 years old, police said.

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This was an unorthodox win for Erick Lindgren, a professional poker player. Instead of winning in a game of poker, as would be expected, he won $340,000 (approximately £259,000) in a game of golf. Hitting five legs on a parlay isn’t a common occurrence, but one bettor made it happen. The anonymous bettor at MGM Resorts placed an $8,500 parlay, betting on the Detroit Lions to beat the New York Giants in the fifth leg.

• In the hours before kickoff, Hill was ESPN BET’s most bet player to score a touchdown and the second-most bet for all other props at over 80 receiving yards, trailing only Trevor Lawrence’s over 200 passing yards.
• Sportsbooks told ESPN that they actually had a winning day Friday, despite the run of favorites.
• In college football betting, top teams will typically schedule opponents they perceive as easy wins in their non-conference schedule early in the season.
• He chose his horses very carefully but didn’t believe much would come out of it.
• Her luck ran out, however, when a drunk driver rear-ended her a few weeks after her life-changing win.
• Michael Leboff is a long-suffering Islanders fan, but a long-profiting sports bettor with 10 years of experience in the gambling industry.
• Richard was so impressed with Hamilton’s skills that he went on to spend several hundred pounds betting on him.
• Her sister died in the car accident while Cynthia was left paralyzed from the chest down.
• The league is investigating whether Ortiz pre-determined the outcome of certain pitches, which were flagged due to unusual betting patterns.
• There’s risk involved in all sports betting, and it’s important for bettors to understand these risks and bet responsibly.
• “Certainly, prop bets, depending on how precise they are, lend themselves to more shenanigans than other kinds of bets,” NBA Commissioner Adam Silver said in May.
• Approaching a slot machine that “spoke” to her, she explained her dire situation to the machine and asked for good luck.
• Supreme Court cleared the way for states to offer sports betting, each successive year has set a record for the amount of money wagered legally.
• No. 12 seed High Point earned the largest upset, stunning 5-seed Wisconsin as a 10.5-point underdog.

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Not satisfied just yet, Sean Connery left all his winnings on 17 once more, and 17 rolled up for the third time in a row, beating the incredible odds of 50,000/1. He collected 17 million lire (approximately £10,000) which would be about  £163,000 in today’s market. While the odds are rarely ever in your favour when you’re placing bets, the stars can align at times and help you take home massive winnings.

Take a look at what sports we are ready to suggest to you and think about what you are interested in most of all. Football, basketball, ice hockey, and tennis are the options picked most frequently. The phrase “good teams win but great teams cover” applies to the Huskies more than most.

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Unfortunately, not all of the biggest betting wins in history have a happy ending. Cynthia Jay-Brennan sat down at the Megabucks Slot Machine during her mother-in-law’s birthday party in 2000. Within just a few minutes, Cynthia won the jackpot, receiving $34.95 million, the biggest-ever Megabucks win at the time.

Philadelphia is still the favorite (denoted by the minus sign) and New York is still the underdog (denoted by the plus sign), but number-shifting could push more bettors towards New England. Not everyone can go home with the biggest sports betting win in history or earn millions of dollars after a single night at a casino. The odds of that happening are incredibly slim, but there’s always a chance! You never know when lady luck might cast her glance on you, and that’s precisely why so many people are drawn to gambling.

How come the rich just keep getting richer, no matter what they do? Before the turn of the century, Australian billionaire Kerry Packer decided to try his luck at baccarat and blackjack, accumulating several astonishing wins in a single evening. It’s estimated that he took anywhere between $20 million and $40 million – the exact figure is unknown since he had quite a few wins over the course of the evening. In September 2018, an anonymous gambler joined the Mega Moolah at the Grand Mondial Online Casino and posted just a $0.75 deposit.

We can’t talk about the biggest betting wins in the UK without mentioning Mick Gibbs. Before the turn of the century, Gibbs placed a £2.50 football bet, forecasting the results of no less than nine football games around Europe. The accumulator bet made him £157,000 richer, and while these winnings were incredible by themselves, Gibbs’ good fortune hadn’t left him yet. His next win somehow topped that measly £157,000, and we’ll discuss that as well. It was the first time favorites won every game in a single day in the opening round since 1992, but it didn’t lead to a hot streak for the betting public.

Today’s top games, best bets, odds: NBA, MLB and more

DraftKings and FanDuel spent heavily on what turned out to be a Missouri ballot initiative record $43 million campaign. In light of Porter’s banishment, BetMGM Sportsbook said in October that it would not take NBA prop bets on players on two-way or 10-day contracts. It joined several others taking this action, including U.S. sportsbook giants DraftKings and FanDuel, as well as ESPN BET. Supreme Court cleared the way for states to offer sports betting, each successive year has set a record for the amount of money wagered legally.

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For 2026, this also figures heavily into the women’s side, where UConn has been a favorite all tournament and is getting 6.5 points against South Carolina in the Final Four. The lack of Connecticut bettors hasn’t stopped the Huskies from racking up substantial action, with 87% of the handle backing their spread for Friday night. The Huskies’ spread has garnered 57% of the wagers and 55% of the money at DraftKings, as well as a majority of the bets (64%) and handle (56%) on the moneyline of +110. BetMGM has seen some solid action backing the Illini, but characterized the spread movement as “a market move.” Everything that happens in sports has additional context when viewed from a betting perspective. From season-changing injuries to record-setting moments and so much more, the news cycle will constantly and significantly affect the sports betting industry.

Peter, a Norwegian online gambler, learned that first-hand when he won €11.7 million in a game of progressive jackpot slots at Betsson online casino. To celebrate her retirement, now a former teacher Beverly Whitten decided to treat herself by testing her luck at the slots. But, after two hours at the “Golden Chamber”, Beverly was shocked to see that she hit the jackpot of $3.7 million! Not knowing what to do with all of that cash, she made a deal with the casino to receive her prize in installments of $1,945 a month. He ended up losing all of his winnings right there in Monte Carlo.

His attorney previously said the vast majority of the $22 million he stole was to subsidize gambling losses. Some form of sports gambling is legal and regulated in 38 states, as well as Washington, D.C., and Puerto Rico. Barkley’s rushing total was set at 110.5 yards, and he finished with 57. He rushed for more than 100 yards in his five prior games and nine of 10. Winning and losing money… for millions of fans, like these guys, it’s one more reason to watch and enjoy sports. Holmes has pitched very well so far this season and bright spots for the Mets have been few and far between; he comes in with a 1.50 ERA in his three starts.

It might be considered easier to lose a spread bet due to the randomness of sports (garbage time touchdown, basketball heave at the buzzer, etc.), but that risk exists across all sports betting markets. One of the biggest long shots in betting history goes to Tayla Polia, who successfully beat 20,000 to 1 odds and won $100,005 in 2015. The 26-year-old placed an astonishing 15-leg NFL parlay with a $5 deposit and earned her winnings by choosing the right point spread in 14 games. Whether it’s hitting the jackpot, lucking out at the roulette table, or placing the perfect bet on betting sites, take a look at a few of the biggest betting wins in the UK and abroad in the past few decades. In April 2023, the NFL suspended four then-Detroit Lions players — Jameson Williams, Quintez Cephus, C.J. Moore and Stanley Berryhill — and then-Washington Commanders defensive end Shaka Toney for sports betting. Williams and Berryhill received six-game suspensions for betting on non-NFL games from an NFL facility, while Cephus, Moore and Toney were suspended indefinitely for betting on NFL games.