Biggest Sports Betting Wins

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Picks betting, celebrities, Gamblers anonymous, Gambling, las vegas, Sporting Events, Sports Betting, sports gambling Updated November 17, 2019 — With the Houston Astros in the 2019 World Series versus the Washington Nationals we got to see the newest big wager on a Jon Price scale of $3.5 million dollars. Here’s a list of some of the largest sports betting wins of all time: 25. Adrian Hayward – £25,000 on a £200 bet In 2005, Liverpool fan Adrian Hayward bet £200 on midfielder Xabi Alonso that he would score from his own half at odds of 125-1. Leicester City winning the Premier League in 2015 was one of the biggest upset wins in this history of sports. Before the season had started they were 5000/1 underdogs but someone was willing to take a shot on them to win it all. A bettor placed a wager of £ 100 and walked away with £200,000. 13 hours ago  First State wins big with sports betting during NFL season Feb 6th, 2021 by Craig Anderson Comments: 0 Patrons place their wagers in the sports betting room at Dover Downs. But if you raise and lower your bets correctly and win a lot of money, the dealer may notice, and the casino may ask you to leave. The MIT gamblers got around this problem by working as a team. A few members would count cards and signal the counts to a third member, who’d bet big exclusively at high count tables. Then other members would.

  1. Sports Betting Winners
  2. Sports Betting Odds


One of the most exciting aspects of sports betting is that anybody can win big, amateur or pro.

The catch, though, is that you either have to bet long odds or risk lots of money. But some bettors have proven that the risk is worth the reward in either case.

Several sports bettors have gotten rich off one or more successful wagers. Even Drake’s dad recently netted six figures with a huge betting win.

Below, you can see more on Dennis Graham’s story, along with other gamblers who’ve won big with sports gambling.

Dennis Graham

Dennis Graham is known first and foremost as the father of Aubrey Graham (a.k.a. Drake). While his son may be one of the world’s biggest hip-hop icons today, Dennis was the first musician in the family.

Graham started playing drums in 1962. He used a makeshift setup that included round tin tubs that people used to bathe in.

James Brown’s drummer gave Dennis his first reel set of drums. This gift helped pave the way for his eventual career, which included drumming for Jerry Lee Lewis.

In more recent years, Graham has started a hip-hop career of his own. He released his first single in 2017, “Kinda Crazy”. Dennis was also featured on the cover of Drake’s 2017 album, “More Life”.

What does any of this have to do with sports betting?

Well, Graham recently wagered $100,000 on the Toronto Raptors winning the 2019 NBA championship. The Raptors were underdogs to the two-time defending champs, the Golden State Warriors.

However, Dennis wasn’t phased and decided to put a six-figure sum down on Toronto anyway. He was likely inspired to do so by Drake, who’s the global ambassador for his hometown Raptors.

Graham was rewarded handsomely when Toronto pulled off the upset, winning the series four games to two. Drake’s dad, meanwhile, pocketed $300,000 after taking the Raptors at 3-1 odds.

Sir Ride A Lot

The 2017 World Series was one of the best in recent memory. The LA Dodgers and Houston Astros went the full seven games, with the Astros pulling out the victory.

An interesting side story involving an Eastern European gambler developed on the side of the World Series. The anonymous gambler, who became known as “Sir Ride A Lot,” placed enormous wagers on the first six games.

Of course, betting big on baseball’s premiere event isn’t a story in itself. But the fact that this gambler let his winnings ride after every game is.

He accumulated $6 million in profits after five successful bets in five games. The logical thing to do in this situation would’ve been to pocket the multimillion-dollar win, or at least only bet a portion of it.

Sir Ride A Lot had other ideas, though. He wagered all $6 million on the Dodgers (-126) winning Game 6. His hot streak continued as LA won and his winnings soared up to $14 million.

He actually thought about risking the $14 million on Game 7. However, the temptation to keep the eight-figure fortune was too great and he stopped betting.

Haralabos Voulgaris

The first couple of gamblers covered in this post were the beneficiaries of incredible luck. But Haralabos Voulgaris (a.k.a. H-Bob) is a professional bettor who’s earned millions of dollars through skill alone.

Sports Betting Winners

Voulgaris’ journey towards success began in the early 2000s, when he discovered that bookmakers were setting inefficient NBA halftime totals.

Sportsbooks weren’t accounting for how fourth quarters normally feature more scoring due to foul-clogged endings. Instead, they priced each half at roughly the same amount each time.

H-Bob began taking the “over” with second-half totals and making a fortune. He’d collect millions of dollars before bookmakers realized and adjusted their strategies.

Voulgaris wasn’t done yet, though, because he developed a betting algorithm in the mid-2000s. He used this program to continue building on his fortune.

He’s since parlayed his immense knowledge of the NBA into a front-office job with the Dallas Mavericks. He also still has much of the fortune that he made by gambling on basketball.

Billy Walters

Billy Walters is another professional bettor who used his wits to win big. Walters started his professional life as a car salesman in Kentucky.

He quickly proved a success at this job, before deciding to bolt to Las Vegas. Here, Walters partnered with the “Computer Team” to dominate the sports betting world.

They were named the Computer Team because they were among the rare gamblers using PCs in the 1980s. Their early knowledge of computers paid off, as they were able to calculate advanced metrics.

Walters continued winning big bets long after bookmakers caught up to the Computer Team’s ways. His crowning achievement is when he won $3.5 million on Super Bowl 44.

He had a good feeling about the New Orleans Saints toppling the favored Indianapolis Colts. His intuition paid off when the Saints won 31-17.

Walters admits that he used bad bankroll management in this case. But few can argue with the result. Unfortunately, Billy was convicted in an insider-trading scandal involving Dean Foods. He’s now serving a stint in federal prison.

Gerry McIlroy

Rory McIlroy is one of the most successful golfers of all time. He has four Major titles and 14 overall PGA tournament wins.

It appears that McIlroy was always destined to be a success. However, this wasn’t entirely the case when he was growing up in Northern Ireland.

Nevertheless, his father, Gerry, placed a bet on his teenage son winning the British Open within 10 years. The proud dad bet £200 at 500 to 1 odds that Rory would soon be a British Open champ.

Rory was 15 when the bet was made and went on to win the Open at age 24. His father pocketed £100,000 as a result.

50 Cent

Curtis Jackson (a.k.a. 50 Cent) is a New York native who loves the Giants. That said, he was looking to bet big when the G-Men made Super Bowl 46.

Sports

50 first caught betting hysteria when New York played the San Francisco 49ers in the 2011 NFC Championship. He won a $500,000 wager when the Giants pulled out a 20-17 overtime victory.

Next up was an even tougher task, the undefeated New England Patriots. Jackson bet $1 million on the underdog Giants and was successful again when they won 21-17.

An interesting side story here is that fellow rapper Birdman wanted to bet $5 million against Jackson. 50 declined the $5 million amount, but was willing to wager $1 million against Birdman.

The latter thought the stakes were too low and turned Jackson down. However, 50 did find a sportsbook that took the bet.

Mick Gibbs

Mick Gibbs was just a simple roofer from Staffordshire, UK, when he decided to make a life-changing bet. He wagered 30 pence on a 15-team soccer accumulator.

The odds of him winning were just 1.67 million to 1. He was on his way to defying the odds, though, when the first 14 teams won.

The final game involved Bayern Munich and Valencia. Gibbs had Bayern winning this Champions League final.

The match provided extra suspense by going to penalty kicks. Bayern Munich emerged victorious, giving Gibbs a £500,000 payout on his tiny original bet.

Fred Craggs

Fred Craggs is similar to Mick Gibbs in that he was just a simple man before sports betting changed his life. The fertilizer salesman decided to make an eight-horse parlay wager on his 60th birthday.

He risked 50 pence on the bet and didn’t take much time looking over the selections. His odds of winning were 2 million to 1.

Craggs walked into a William Hill betting shop later on to make more bets. He didn’t realize, though, that his parlay had been successful.

He should’ve actually won £1.4 million on the wager. But William Hill’s terms capped his parlay win at £1 million.

Regardless, he was still extremely happy about the win. Craggs was able to retire earlier than expected afterward.

Odds

Conclusion

You can see that people from all walks of life are capable of winning big in sports gambling. Some are skilled pros who develop a great strategy, while others are amateurs who’ve defied the odds.

Sports Betting Odds

Drake’s dad is the latest remarkable story from the sports betting world. He risked quite a bit ($100k) on the Raptors winning, but was well rewarded with a $300,000 payout.

Sir Ride A Lot brings another impressive tale. He let his winnings ride on six straight World Series games, earning a combined $14 million as a result.

Haralabos Voulgaris and Billy Walters both relied on strategy rather than luck to win big. Both have made millions from sports gambling over their careers.

50 Cent, Gerry McIlroy, Fred Craggs, and Mick Gibbs are a few more cases of being lucky, rather than great bettors. Nevertheless, they all profited big from sports wagering as well.

DOVER — Are you ready for some football, Delaware?

If the Chiefs hoist the Vince Lombardi Trophy again tonight, that’s good news for the First State’s coffers.

The state of Delaware gains $104,000 for its General Fund with a Kansas City Super Bowl LV win and loses $15,100 with a Tampa Bay upset.

That’s based on futures bets — wagering on a team to win the Super Bowl at ever-changing odds throughout the year.

In the futures wagering, favorite Kansas City’s odds began at 4-1 in September and dropped to 9-5 in December, meaning there was less risk to the state if bettors cashed in.

The Buccaneers were a longer shot to win (12-1 at the season’s opening kickoff and throughout the year), meaning the payoff would be higher for bettors.

Whether Tampa’s Tom Brady is a champion again or the Chiefs’ Patrick Mahomes repeats as No. 1, the First State will add millions of dollars to its coffers overall.

Heading into the final week, the Delaware Sports Lottery held on to $22.4 million of $61.1 million wagered on NFL and NCAA games.

The ultimate overall outcome wasn’t certain, due to ongoing bets right up to the big game today.

Basketball

Kickoff is scheduled for 6:30 p.m. at Raymond James Stadium in Tampa, Florida.

The state figures to make out pretty well this year on professional and college sports bets placed at Delaware’s three casinos and at retailers throughout the state.

After paying off the state’s three casino sportsbooks in Dover, Harrington and Wilmington, along with vendors and retailers, the Delaware Sports Lottery will deposit the remaining profits into the General Fund, state Lottery Director Vernon Kirk said. That amounted to $9 million as the Super Bowl approached, with several days of wagering remaining.

Mr. Kirk called the football numbers “outstanding” and attributed much of the state’s success to the uncertainty that COVID-19 brought to the season.

Gauging team’s potential performances was perhaps more challenging due to uncertain player availability and scheduling upheavals that marked many games played in the 2020-21 season, according to Mr. Kirk.

“We were very lucky in that regard,” he said.

Delawareans’ ongoing preference to parlay cards continued to pay off, as well, Mr. Kirk said. Where single-game bets require just one team to come through, the only way to win a parlay is to correctly pick at least three outcomes, albeit at higher payoffs if successful.

Since their inception in 2009, the state has always marketed parlay cards as a more recreational experience, Mr. Kirk said, “and people got used to it.

“It was promoted more of a fun, casual venture to have fun with, not something that’s seen as making an investment (in an attempt to make serious money).”

The final parlay card to this season includes propositions such as:

• Coin toss heads or tails.

• Team with the shortest made field goal in the game.

• First team to commit an accepted penalty.

• Team with last possession of the game.

• Passing yards by Mr. Mahomes, even or odd number.

• Passing yards by Mr. Brady, even or odd number.

• Total points by Chiefs, even or odd number.

• Total points by Buccaneers, even or odd number.

Going 3-for-3 on selections would earn $6.50 for every dollar bet. Payoffs increase from there, topped by 10-for-10 earning $800 per dollar. Minimum wagers are $2.

At Cheswold News & Tobacco, a steady stream of would-be bettors entered the doors last week for the final parlay card of the gridiron season.

“They’re taking cards, and I’m sure they’re going to make some interesting bets,” owner Dave Hollen said. “If it’s football season, (then) people are going to come in and play. We’re probably up in parlays compared to last year.

“It may have been a bit slower to start the season due to coronavirus, but once people got used to the hours, the distancing, the masks, it was pretty much the same it’s always been.”

At Mike’s Food Market in Milford, however, owner Mike Patel wasn’t feeling so fortunate.

“The parlays have been down during the coronavirus. Maybe people don’t have a lot of money,” he said. “(It’s not as exciting), but there’s nothing we can do about it.”

There are still single bets available today at Dover Downs Hotel & Casino, Harrington Casino & Raceway and Delaware Park sportsbooks, starting with the spread that listed the Chiefs as a three-point favorite.

Money to Delaware

The First State’s General Fund has received approximately $13 million from all sports wagering (football, baseball, basketball, etc.) from July 1, 2020, to Jan. 31, 2021.

Pro football futures wagering dropped from approximately $327,000 out of $67.7 million overall last year to $217,600 out of $66.1 million this year, Mr. Kirk said.

College football wagering also dropped, due to games canceled by the COVID-19 pandemic, Mr. Kirk said, but the NFL was less affected due to being able to play all scheduled games, even if delayed.

Biggest

The 2020 numbers through the start of last week included:

• College football (straight bets) — $7.9 million.

• Professional football (straight bets) — $22.3 million.

• College and professional football (parlay bets) — $35.9 million.

The overall 2019 numbers included:

• College football (straight bets) — $10.6 million.

• Professional football (straight bets) — $22 million.

• College and professional football (parlay bets) — $35.1 million.

The sportsbooks receive 40% of money not returned to bettors, while the state’s General Fund receives 50% (less administrative expenses). The other 10% goes to supplement purses through the Delaware Thoroughbred Horsemen’s Association and the Delaware Standardbred Owners Association.

Betting

Retailers receive a commission of 5% of parlay sales, while money also goes to winning players and vendors. Delaware takes 90% of the handle (minus administrative costs) for the General Fund, while 10% goes to supplement purses offered at DTHA and DSOA tracks.

Across the country

According to American Gaming Association research, 23.2 million Americans nationally plan to bet a total of $4.3 billion on this year’s Super Bowl. There’s been a huge uptick in online sportsbook wagering, where the AGA said a record 7.6 million persons will take part, a 63% increase from the year before.

“This year’s Super Bowl is expected to generate the largest single-event legal handle in American sports-betting history,” said AGA President and CEO Bill Miller. “With a robust legal market, Americans are abandoning illegal bookies and taking their action into the regulated marketplace in record numbers.”

Colorado, Illinois, Michigan, Montana, Tennessee, Virginia and Washington, D.C., have added legal sports-betting opportunities since last year’s Super Bowl. That means another 36 million adults can place wagers in their home state, the AGA said.

According to the AGA, key findings from its research (conducted by Morning Consult) indicate shifting betting patterns during the COVID-19 pandemic:

• 1.4 million Americans plan to bet in person at a sportsbook, down 61% from 2020.

• 1.8 million bettors plan to place a bet with a bookie, down 21%.

• 4.5 million Americans plan to place a pool, squares or similar bet, down 19%.

• 11.9 million Americans plan to bet casually with friends, down 18%.

• 56% of bettors plan to bet on the Chiefs, while 44% plan to bet on the Buccaneers.

Reach staff writer Craig Anderson at canderson@newszap.com