Famous Sports Bettors – The Best Minds In The Business

There are several individuals who managed to make a full career off of betting on sports. Additionally, there are famous well-known names who are in the sports betting world. Famous sports bettors can be viewed as prime examples of just how high players can get betting on sports. From those who have made a living off of sports betting like Haralabos “Bob” Voulgaris to famous superstars like Floyd Mayweather who are big sports betting advocates, the sports betting arena is filled with well-known names helping to push the market even further. Here bettors will learn about some of the biggest names in legal sports betting.

This page will introduce you to some of the biggest and most successful famous sports bettors out there. These sports bettors have made a name for themselves by betting on their favorite sports. They place action on the same odds that anyone has access to, which makes sports betting all the more engaging. It’s always fun to watch someone succeed where so many have failed.

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What Do All Famous Sports Bettors Have In Common?

Trial and error is a major part of sports betting and something that all famous sports bettors have in common when betting on sports. No one is just born with the right strategy that works for them. It takes plenty of knowledge to play this game and be a success at it which is what makes gambling on sports a continuous learning experience.

Research, familiarity of the sport, betting splits, money management, and an understanding of the odds are each factors that play into how famous sports bettors have made their winnings. It all comes down to numbers, be it the odds or the money at stake and all bettors need to know these things. They also learn early on or not so early on to gamble conservatively until they find that strategic sweet spot that each one of them stumbles on at one point or another during their careers.

Having the discipline and self-control to bet only on the wagers that make sense for a payout is key. Shopping lines for the best wagers is a common practice among this crowd as well. And knowing that even the best gamblers will lose helps to ease the blow when it happens because each of these famous sports bettors has lost about as many times as they’ve won, they’ve just managed their money well enough that they’re in the green rather than the red and that’s a place every gambler of the games wants to be.

Ben “Parlay Patz” Patz

Benjamin Tucker Patz was a rising star on the sports betting scene in 2019 at just the young age of 22. He was always interested in wagering on sporting events, becoming a member of an online sportsbook as soon as he was 18. Patz made his fame on a handful of parlay bets, which he converted into almost $1M in payouts. He was a phenom in the sports betting world and rose to stardom due to his success and money. However, 2020 saw Ben was charged for threatening the lives of athletes and their family members after an FBI subpoena and warrant found that Patz had made over 300 death threats to professional and collegiate athletes. Patz would message young college athletes on social media with death threats following a big loss that hurt Patz’s bankroll.

Click here to learn more about the sports betting history of Parlay Patz.

William T. “Billy” Walters

Billy Walters holds the distinction of having “bet more money more successfully than anyone in history,” and he holds it closer to the vest than you might imagine. The glitz-and-glamor world of high stakes betting never seemed to attract Walters – he often had employees, called “runners,” post his bets remotely – partly because he was so good sportsbooks stopped taking his action. Walters has never been particularly explicit about his methodologies, but is estimated to have earned roughly $300 million by taking on the stock market, real estate risks, and epic sportsbook gambles. Walters was convicted of insider trading on Dean Foods stock, fined $10 million, and sentenced to 5 years in the clink. Walters received a pardon from Donald Trump and was released in 2020.

Click here for the full sports betting history of Billy Walters.

Marco D’Angelo

One of the most noteworthy contemporary practitioners of playing both sides of Las Vegas is one Marco D’Angelo, a Las Vegas resident who regularly posted between a 57- and 58-percent success rate on his sports picks. He once had a run of correctly choosing 25 MLB games in a row, a feat not often replicated in betting circles, and he has a reputation of going with his gut as much or more than he goes with the science and the metrics. D’Angelo is currently the president of WagerTalk.com, and still offers picks as one of the most successful touts in the industry, with over 45,000 followers on his twitter account.

More on Marco D’Angelo’s sports betting history can be found here.

John Price

Unlike the legendary Billy Walters above, Jon Price has a firm background in statistics and a mathematics degree from NYU. Price is most famous for two bets. First, he put placing a million bucks on Super Bowl XLIX between the Patriots and the Seahawks, and claims to have cashed out thanks to that last minute Malcolm Butler interception. Second, Price picked the Royals to win the World Series before the 2015 season started, putting $22,000 on it, and he won $264,000 on that pick. Price operates more on the sports handicapping and tout side of the business now. He is a frequent radio guest on sports betting shows throughout the entire country, giving free picks and analysis on the week’s games.

See John Price’s full sports betting history here.

Teddy “Covers” Servansky

While it was Jimmy The Greek who brought the betting line into the average American household, it is Teddy Covers who’s working overtime to make sure it stays there. Since the 1990s, Covers has been making and selling picks on a variety of sports matchups through a variety of media, appearing in magazines, newspapers, radio, and television shows. He has the cachet to cash out on his choices because of his acumen in finishing at or near the top in over half a dozen major sportsbook tournaments throughout the 1990s and 2000s, including the Las Vegas Hilton SuperContest, an event that the next guy on the list actually won twice. Currently, Teddy Covers works for WagerTalk, the company that Marco D’angelo is the president of, hosting longform video and audio content.

Read more about Teddy Covers sports betting info.

Haralabos “Bob” Voulgaris

Bob Voulgaris was perhaps the most prolific and successful NBA bettor on Earth. In the late 1990s at the age of just 25, Voulgaris was reportedly flipping a million dollars a day on basketball games. His most famous “edge” was in taking advantage of the unsophisticated way NBA bookmakers of the time predicted halftime scores, which arely accounted for the aberrant burst of scoring in the fourth quarters of games. Thus, Voulgaris pounce on predictions that were far too low at the half. He was also well-known for seeking out the “tells” and tendencies of head coaches Eddie Jordan, Jerry Sloan, and Byron Scott. His analytical mind led to a tenure as a consultant for the Dallas Mavericks of the NBA.

See the Bob Voulgaris sports betting bio here.

Jimmy Snyder

Jimmy Snyder, a.k.a. Jimmy The Greek, was a celebrity bettor, Vegas bookmaker, and television sports commentator. Jimmy was one of the first people to bring betting tips to live TV, discussing predicted final scores of games as a method of discussing spreads. He was ultimately canned by CBS for racially biased comments.. Saying what he said was probably the worst bet of his career, and he wagered – and lost – his longtime gig on CBS’ Sunday morning show “The NFL Today”. Still, whenever you hear guys on the TV tell you what the specific final score of a given football game will be, remember Jimmy The Greek.

Read Jimmy The Greek’s Sports Betting History Here.

Steve Fezzik

A math whiz and champion-level chess player, Steve Fezzik made his start as a sports bettor in the 1990s, mainly playing the college football books in Las Vegas. He moved there permanently in 2001, and during the aughts, he won half a dozen high-profile tournaments and pocketed nearly a million dollars. In 2008, Fezzik won the Las Vegas Hilton SuperContest, considered by many to be the “World Series of sports betting.” He won it again in 2009, and he remains the only two-time winner of the prestigious event. Currently, Fezzik makes his money as a tout, selling picks on SteveFezzik.com, and famously stays away from pregame plays.

Learn more about the sports betting history of Steve Fezzik.

Anthony Grant “Tony” “The Lizard” Bloom

Englander Tony Bloom is described as “the cleverest man to ever place a bet”, and his success bears it out by miles. He started as a poker player, winning tournaments for fun, and acquiring the nickname “The Lizard” for his cold-blooded calculating nature. Then, he moved towards soccer. His company, StarLizard, is a betting consultancy firm that effectively operates as an investment vehicle for big money players, accepting only those who can invest more than $2 million. His success has been such that he’s pumped hundreds of millions of pounds into his favorite childhood soccer team, Brighton and Hove Albion FC, after purchasing it outright. Tony Bloom could very well be the most successful sports bettor of all time.

View the sports betting history of Tony “The Lizard” Bloom.

Floyd Money Mayweather

One of the biggest names in all of sports is Floyd Mayweather, and he also happens to be a huge sports bettor. Being a resident of Las Vegas within one of the most friendly legal sports betting states, Floyd has made the news on multiple occasions for his big bets that he has made over the years. Mayweather’s sports wagering strategy is largely based on picking a favorite and then dumping a huge amount of money on that favorite. It’s a bit of a fish move, but Mayweather has the money to burn – and a decent success rate. He once famously bet a million dollars on the Oregon Ducks in a random regular season game, and won. This is an illustration of his strategy to throw money around on spread favorites.

Floyd Money Mayweather’s sports betting history can be found here.

Zeljko Ranogajec

The Australian child of Croatian immigrant parents, Zeljko Ranogajec is, by some accounts, the wealthiest gambler in history. His annual turnover is estimated at more than a billion dollars. Zelj was described by contemporaries as one of the single best advantage gamblers of all time. Zelj made his move into the sports betting world via horse racing. Zelj is allegedly responsible for anywhere between 6% and 30% of several Australian racebook’s total handle. Zelj left Australia in 2019, and founded Colossus Bets in the UK. He claims his wealth is exaggerated, but it has been claimed to be around $600 million.

Learn more about Zeljko Ranogajec’s sports betting history.

Ashton Kutcher

Actor Ashton Kutcher does not at all mirror the character that made him famous, Michael Kelso, from “That 70’s Show.” In his earlier days, he made money betting on college football between acting gigs. Kutcher claims to have been a runner for what he described as the largest sports betting syndicate in America, sparking rumors that he worked with Billy Walters. After his fame, Kutcher was still aware of the potential sports betting held. Kutcher became a venture capital funder of Unikrn, an esports sportsbook, in 2015. In 2017, Unikrn partnered with MGM Resorts International to be able to host events in the Vegas area. Unikrn was sold to Entain in 2021, likely netting Kutcher his biggest betting payoff.

Read Ashton Kutcher’s sports betting bio here.

James “Jeopardy” Holzhauer

At 34 years old, James Holzhauer was made famous by stringing together an epic, record-shattering series of Jeopardy wins. Holzhauer used a value-based strategy to dominate the game, and his experience as a sports bettor helped him develop it. Holzhauer has been betting on sports since 2006, and during the infamous Jeopardy Q&A sessions, he’s given US viewers little tidbits of insight about how the sports wagering world works. Holzhauer has also served as an advocate for the regulation of sports betting nationwide. Holzhauer is not famous for sports betting per se, but he’s a great example of how the skills developed betting on sports apply to other intellectual pursuits.

Learn the full sports betting history of James Holzhauer.

Michael Jordan

Michael Jordan, the greatest NBA player of all time, has always been a bit of a degenerate gambler. It should stand to reason that he would enjoy the hobby of sports betting as Jordan cannot get enough of the spirit of competition. Jordan has no set way of going about his hobby, no specific algorithm to win it. Instead, he places wagers simply because he loves the idea of winning. He has bet on games of Rock, Paper, Scissors with the same zest that he would on the NBA Finals. Some even speculate that his retirement in the mid-1990s was due to a hidden gambling scandal, although this is regarded as unlikely.

Read Michael Jordan’s sports betting history

Bill “KrackMan” Krackomberger

Bill “KrackMan” Krackomberger is a major name in the sports betting world with over 25 years as a famous bettor. Nowadays KrackMan Is selling pciks on his KrackWins app to members for a variety of sporting events. He also spends a lot of time educated sports bettors on the dangers of gambling addiction, playing smart, and keeping family first. Krackonberger is one of the biggest sports bettors in the country with roots in the Las Vegas betting scene alongside the likes of Floyd Mayweather.

Learn more about the KrackMan with our Bill Krackomberger sports betting bio!

Pete Rose

Pete Rose played in Major League Baseball for 23 years. He gained the nickname “Charlie Hustle” playing five separate positions on his team. He then became a manager for the Cincinnati Reds for five years. He was arguably one of the greatest players of all time, but he is not in the MLB Hall Of Fame due to his rampant sports gambling. Rose maintained for years that he never bet on his own team, but then admitted that he had, in fact, wagered on the Reds. He now claims he only bet on them to win, but that’s still a tough thing to do, because it means that there were games that he did not bet on them to win as well – which disrupted the integrity of the game.

What is Charlie Hustle up to now? Find out by reading the full Pete Rose sports betting bio.

Jim ‘Mattress Mack’ McIngvale

Jim McIngvale is a Houston-based furniture mogul known colloquially to Houstonites as “Mattress Mack”. Mack is famous for making outlandish sports bets. His most famous wager was when he bet $13 million on the Houston Astros to win the 2019 World Series, which they did not. Mack famously has to travel to other states to place his wagers, as Texas doesn’t have state-regulated books. He isn’t entirely insane, as he ties in his massive wagers to his Gallery Furniture store promotions. In other words, he basically hedges his big sales with big wagers – either he doesn’t offer the sale, and gets the promotional benefits of positive coverage from sports betting media, or he wins the wager, which he then uses to cover the costs of the sale.

See more at Mattress Mack’s bio page.

Charles Barkley

Charles Barkley made a name for himself in the ’80s and 90’s as an NBA star. He was one of the elite back in his playing days. Even back then, he enjoyed placing wagers on sporting events. Back in his early sports gambling days, Barkley was still new to the scene so he had not yet set limits for himself. As a famously bad gambler, he racked up significant debts, although he is currently financially stable. Barkley has since set limits to the amounts he allows himself to wager and has gained himself a partnership with DraftKings. Being the face of DraftKings has given him the chance to speak about the greatness of sports betting to the public, and he’s a common feature in DK commercials.

Read Charles Barkley’s sports betting history bio.

Gadoon “Spanky” Kyrollos

Gadoon “Spanky” Kyrollos is practically the definition of old school sports betting. If you want to look for New Jersey charm, Spanky definitely has it. He has been betting on sports for 20 years, and is famous as an advocate for sharps, and against limiting winning players. He definitely lucked out because he can now bet on sports in his home state of New Jersey. Spanky has accumulated millions over his years of sports betting and has created a reputation for himself as one of the biggest sharps in the world. His experience being kicked out of sportsbooks for winning lead to him being a major advocate for traditional sportsbook models as opposed to those that just limit winning players.

Click here for the sports betting history of Gadoon Kyrollos.

Drake

Rapper and singer Drake has become one of the faces of sports betting in the post-regulation era, often posting huge sums of money wagered on sporting outcomes on online betting sites like Stake. It’s unclear whether or not Drake is wagering his own money, or serving in a paid sponsorship role, but he raked in about $700,000 betting on the Los Angeles Rams in the Super Bowl, and about $800,000 betting on the Golden State Warriors to win the Western Conference in 2022. He’s had some losses too, but like he says, “I’m here for a good time not a long time”.

See more at Drake’s sports betting bio page.

Trainwreck

Trainwreck, who streams on TrainwrecksTV, recently began sports betting in addition to his Twitch streaming career. In July, he posted a $2.7 million parlay that he won, parlaying an Everton FC win with a Chelsea vs. Leicester City draw and an Aston Villa Vs. Burnley draw. His stake was about $77,000, and he cashed out almost three million. Trainwreck has been at the center of controversies regarding Twitch and gambling streams before, and the streamer – whose real name is Tyler Niknam – has recently leaned fully into sports betting and gambling as a method of content creation.

Phil Mickelson

Phil Mickelson may not be famous for sports betting because of his winnings, but he has certainly made a name for himself over the years in the community. It was mentioned in a book by Billy Walters that Phil Mickelson has lost over $100 million in gambling in the past. In a 2023 tweet, he stated on Twitter that he would be taking a break from betting on football, as he crossed the line between fun and moderation.

Check out more about the sports betting history of Phil Mickelson and how he put his name with the greats.

Why Do So Many Famous Sports Bettors Use Crypto?

Tons of the names you’ll see on this page are heavy crypto investors. Haralabos Voulgaris was famously long on Bitcoin since before 2015. This is partly because of the large deposits that Bitcoin sportsbooks accept. Most famous sports bettors are putting down way more money than the average bettor, meaning they need sportsbooks that will take their wagers. Crypto also offers the biggest sportsbook bonuses, opening the door for even bigger bets.

Most Famous Super Bowl Wagers

With betting on the Super Bowl being the single biggest event for sportsbooks in the US every year, it is no surprise that many famous bettors wager heavily on the big game. Some lucky bettors even become famous because of their Super Bowl bets.

Super Bowl 53 – “Bettor X” placed $3.8 million on the Rams to win Super Bowl LIII in 2019. The Rams would go on to lose this, putting the infamous bettor in big losses. Bettor X famously won more than $20 million betting on the World Series and Super Bowl LII the year prior, so even with this massive loss, they wouldn’t be hurting too bad.
Super Bowl 55 – Jim “Mattress Mack” McIngvale famously wagered $3.46 million on the Tampa Buccaneers +3.5 spread during Super Bowl 55. When the Buccaneers finished with an upset over the Kansas City Chiefs, Mattress Mack collected $6.18 million in winnings.
Super Bowl 56 – Texas entrepreneur and legendary sports betting Mack also put $9.5 million across two bets on the Cincinnati Bengals to win Super Bowl 56.
Super Bowl 57 – Mattress Mack placed two separate wagers of $1 million each on the Dallas Cowboys to beat the San Francisco 49ers in the Divisional Round. The Cowboys were the underdog in both tickets and Mack received +165 and +170 odds on the two bet slips.
Super Bowl 57 – Drake dropped $1.1 million on the Kansas City Chiefs’ underdog odds against the Cincinnati Bengals in the AFC Championship game. A Chiefs win would cash over $2 million for this wager for Drake.

Most Famous College Sports Bets

Although the Super Bowl is one of if not the biggest sports betting events of the year, there are some college sporting events that are just as big and gain just as much betting interest from big players. One famous bettor in particular who loves making big bets on college sports is Mattress Mack. The Gallery Furniture owner has placed some notable bets on both college football and basketball over the years. Two of his most notable bets were unfortunately losers. He lost $2.7 million on the Alabama Crimson Tide to win the football National Championship and lost another $1 million on the Houston Cougars to win the 2021 March Madness Tournament. Floyd Mayweather is another big college sports bettor with one of his most famous bets coming back in 2013 when he bet $100,000 on the Miami Hurricanes football team to cover a first-half score against Texas A&M. The Canes were behind Mayweather and cashed him north of $86k.