Famous Sports Bettors – The Best Minds In The Business

One of the most alluring aspects of legal sports betting is the potential to make a career out of it. Anyone who’s ever had any luck on the ponies or in the sportsbooks or at the card table can attest to the desire to go pro. Of course, it sounds a lot easier than it actually is. Generally speaking, the world’s most famous bettors haven’t always lived glamorously, nor have their professions been altogether stress- and drama-free. Just look at (cough, cough) Doc Holliday.

For a long time, it was Doc Holliday’s downward-spiraling, degenerate persona that most aligned itself with the idea of professional gambling – a seedy calling in shady places, the office a smoke-filled den of booze, drugs, and dirty double-dealings. Anyone who became a professional gambler ran the risk of drawing Eights and Aces at any time. It just wasn’t a respectable, gentlemanly job. You only turned to the parlor when you had nothing left to lose.

Of course, that’s the myth aspect, and it really is just a fun, not so pretty fairy tale. The reality is that the world’s most famous bettors – the people who have set the standard in the modern public psyche – are basically just giant math nerds. If these guys weren’t betting, they’d be crunching crazy numbers and running advanced models at some Wall Street firm or yammering endlessly about sabermetrics and comic books on ESPN. Sure, they’ve got ice in their veins, but for the most part, they’re just numbers-obsessed adrenaline junkies and sports fans chasing a thrill.

As you read through the list of some of the world’s most famous sports bettors and peruse their biographies, you’ll find that they all have three things in common. A love of math and numbers, a passion for gaming, and their own personal algorithms or strategies for winning. These three things combined have created some of the best gamblers out there. Understanding the game along with the way the numbers work makes for some of the sharpest, most successful bettors in the sports betting scene, and the gambling scene in general.

William T. “Billy” Walters

If you want to know about famous bettors, you’ll want to know about Billy Walters. He 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. Yes, this was primarily driven by various Las Vegas sportsbooks refusing to do business with the guy, but on some level, the isolation made his analysis and computer modeling even better. But nobody will ever know exactly how some alcoholic used car salesman from Kentucky ever broke his underdog mold to own the sports betting world; in the few interviews he’s given over his 40-year professional life, he’s never been particularly explicit about his methodologies. Walters is estimated to have earned roughly $300 million by taking on the stock market, real estate risks, and epic sportsbook gambles. Statistically speaking, there’s no explanation for Walter’s success. Everyone just assumes he broke science. And everyone knows he broke a heck of a lot better than even. Until recently, at least. Unfortunately, Walters’ fortunes ran out – at least temporarily – in 2017, when he was convicted of insider trading on Dean Foods stock, fined $10 million, and sentenced to 5 years in the clink. Walters is scheduled for release on February 14, 2022, when he will be 75 years old. Read Billy Walters’ sports betting history here.

Haralabos “Bob” Voulgaris

Bob Voulgaris is, by all modern accounts, 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 and profitable “edge” was in taking advantage of the unsophisticated way NBA bookmakers of the time predicted halftime scores. Since they rarely accounted for the aberrant burst of scoring in the fourth quarters of games, the industry standard was to take the presumed final score and merely cut it in half. That made it easy for Voulgaris to pounce on predictions that were far too high at the half, and it is thought that he made tens of millions of dollars during his peak. (Once the bookies wised up, the cash cow dried up, unfortunately.) Though he also relied on the broader statistical sciences of the times, he was also well-known for seeking out the “tells” and tendencies of head coaches Eddie Jordan, Jerry Sloan, and Byron Scott. Unsurprisingly, this style of play lends itself well to poker, where Voulgaris has accumulated almost $2 million in earnings to date. See the Bob Voulgaris sports betting bio here.

John Price

Unlike the legendary Billy Walters above, Jon Price has a firm background in statistics and a mathematics degree from NYU. While he is noteworthy for a placing (and then winning – I still can’t believe they didn’t hand Beast Mode the ball!) a million bucks on Super Bowl XLIX and picking the Royals to win the World Series before the 2015 season started, Price operates more on the sports handicapping side of the business. He is also a frequent radio guest on sports betting shows throughout the entire country giving free picks and analysis on the week’s games. See John’s full bio here.

Marco D’Angelo

Jon Price isn’t the only bettor-turned-handicapper on this list. One of the most noteworthy contemporary practitioners of both sides of the coin is one Marco D’Angelo, a Las Vegas resident who regularly posts 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.

View more about Marco D’Angelo.

Jimmy Snyder

Jimmy Snyder, a.k.a. Jimmy The Greek, was a celebrity bettor, Vegas bookmaker, and television sports commentator. Though his career was mostly lauded due to his magnanimous demeanor and his comical claim that he bet against Thomas Dewey to win the US Presidency because he had a mustache (which, apparently and inexplicably, he decided ladies don’t like), he was ultimately panned and canned by CBS for saying some old-man-style-innocuous-but-decidedly-non-PR nonsense about different “types” of athletes. It 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. He started that to sidestep the “taboo” of positing sports spreads on national television. The guy was truly a pioneer that pushed sports betting into the American living room. Read Jimmy The Greeks 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.

Read more about Teddy Covers

Anthony Grant “Tony” “The Lizard” Bloom

Maybe Zerj is just staying low-profile in his claims of relative pauperhood, or maybe he’s actually not all that (many billions). Well, either way, this guy is. Englander Tony Bloom, like Zerj, cut his teeth playing cards, earning roughly $3.3 million in live tournaments to date. But word is this guy took it to the next level (or three) when he started betting on sports and selling his picks. Focusing primarily on soccer behind the walls of his secretive Starlizard company, which forces its employees to sign strict non-disclosure agreements while allowing them a place in the pool, a bona fide fortune has been amassed almost entirely in secret. If Tony wins, his employees do too, but nobody can know about it. Still, word gets out. And the word on the street is that Tony wins a lot. Like, billions-of-dollars a lot. In reality, the only concrete evidence of Bloom’s personal net worth is the fact that, since about 2009, he’s pumped close to $260 million into his favorite childhood soccer team, Brighton and Hove Albion FC. Which, of course, he now owns.

As for whether he also owns the title of World’s Richest Bettor? Well, I wouldn’t bet against him.

View our Tony “The Lizard” Bloom page for more info.

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. Floyd has made the news on multiple occasions for his big bets that he has made over the year. Of course, he only really tells people about the winners, but they are definitely worth talking about. During the super bowl he has been known to bet over a million dollars on the team he likes. And he usually likes the consensus favorite. Indeed, Mayweather’s sports wagering strategy is largely based on picking a favorite and then dumping a huge amount of money on that favorite. This is not necessarily an effective method for casual or small-money bettors, as the payouts are meager for most folks. But while you or I would be reticent to risk $100 to win $10 on a solid favorite, that ratio scales up nicely. At Mayweather’s price point, $1 million to win $100,000 adds up in a hurry. You gotta have money to make money, right? Check out Money Mayweather’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. Unlike Walters above, Fezzik stays in the limelight, using his name recognition to push his brand onto the covers of news stories and magazines. 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.

Learn all about how Steve Fezzik made his mark in sports betting.

Zeljko Ranogajec

The Australian child of Croatian immigrant parents, Zeljko Ranogajec (hereafter referred to as Zelj because that’s a weird last name to type) is, by some accounts, the wealthiest gambler in history. His annual turnover (that is, how much he spends betting each year) is estimated at more than a billion dollars. A banker by education, he soon cultivated a powerful skillset that would let him earn even faster than the bankers do, routinely turning a few hundred bucks into a couple million per blackjack session. Zelj made his move into the sports betting world when he basically took over the Australian ponies scene. He is alleged to be responsible for significant percentages of revenues from several of Australia’s foremost corporate bookmakers, accounting for between 10 and 30 percent of their yearly business. Notoriously secretive, Zerj was once tracked down by a reporter on holiday, who asked him point-blank about his wealth. Apparently, Zerj responded that reports of his girthy bank account are “all just a big exaggeration.”

Read the full bio.

James “Jeopardy” Holzhauer

At 34 years old, James Holzhauer came onto the scene (in the living rooms of millions of Americans, no less) by stringing together an epic, record-shattering series of Jeopardy wins. However, it’s Holzhauer’s day job that adds to his mystique: he’s a professional sports bettor. In 2004, Ken Jennings set the all-time record for Jeopardy wins with 74 straight victories, and while Holzhauer has a long way to go to top that, he’s currently on pace to shatter KenJen’s $2.5 million in winnings during that 2004 run. 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.

This synergy of time and place is not lost on Holzhauer, who – in 2019 – is directing much of the casual narrative around the legalization of sports wagering nationwide. Holzhauer hasn’t got the career winnings of other gamblers on this list, but as a dominant Jeopardy champion and daily water-cooler topic of discussion, he is helping drive the acceptance of sports wagering as a legitimate skill-based pursuit. Holzhauer is a proponent of in-game wagering (a relatively new phenomenon), and he characterizes his profession as “analyst, trader, fund manager, and day trader all [in] one.” A generation later, people still talk about Ken Jennings. Holzhauer is even better, and nobody is primed to be a long-term, mainstream legal sports betting ambassador quite like this guy.

Learn about James Holzhouer and see how he does it.

Michael Jordan

Michael Jordan has always been a sports fanatic, which is not such a stretch being that he made his bones as a professional athlete. It should stand to reason that he would enjoy the hobby of sports betting as Jordan cannot get enough of the spirit of competition. The ex-NBA star has had a checkered past when it comes to his love of wagering on sporting events. 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 a professional championship game. This love of gambling has given him his fair share of ups and downs in the game. However, he has never given up on seeking that thrill as sports betting remains one of his favorite hobbies. These days, he can be found betting on golf more than any other sport. Read Michael Jordan’s Sports Betting History.

Bill “KrackMan” Krackomberger

Bill “KrackMan” Krackomberger is a Las Vegas institution, one of the more visible sports bettors and sports betting handicappers in the global gambling mecca that is Sin City. While he’s been making and selling picks for a quarter century, since the overturn of PASPA, Krackomberger has been more able to publicly capitalize on his sports wagering prowess nationwide. His KrackWins app – available for iPhone and Android (and unfortunately not called KrackKills, which would have been both apt and really, really funny) – offers tiered memberships for daily and weekly sports picks. But behind all the high-rolling, big-spending swagger, Krackomberger is just as famous in the wagering world for telling gamblers how to temper their approaches, how to put personal and familial financial obligations first, and how to always attentively manage their bankrolls.

Bill Krackomberger is an extremely successful sports bettor with several half-million-dollar wins to his name, but his real message is to keep your expectations – and your outlooks – realistic. As a casual bettor or newcomer to the game, that’s about the best advice you can get.

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 as a player for the league. He then became a manager for the Cincinnati Reds for five years. Throughout his time in the MLB, Rose was a big sports bettor. In fact, his gambling led to his ineligibility to be part of the Major League Baseball Hall of Fame. It was said that Rose would bet on the Reds daily, at $10,000 a game. He’s made it clear that he always put his money on his team to win so that it’s known that there was no “fixing” of games for the Reds to take a dive on purpose. Rose only gambles on the MLB and continues to do so to this day.

With the legalization of sports betting and the MLB embracing it, people are now questioning whether or not this means Rose will no longer be banned from being allowed into the Hall of Fame. Pete Rose currently has a net worth of $3 million. His wife maintains that her husband continues his hobby of betting on the MLB, despite all he’s lost because of it, mainly his shot at a Hall of Fame induction. What is Charlie Hustle up to now? Find out by reading the full Pete Rose sports betting bio.

Ashton Kutcher

Actor Ashton Kutcher does not at all mirror the character that made him famous, Michael Kelso, from “That 70’s Show.” Kutcher has an IQ of 160 and a taste for the math behind the algorithms that go into wagering on sporting events. In his earlier days, he made money betting on college footballs between acting gigs. He worked in conjunction with a top sports betting operator that looked for numerical anomalies within the game in order to come up with the best wagers. Kutcher acted on their behalf by placing the bets at various locations, playing the part of a dumb actor with a lot of money to burn and a love for gambling. He and the company were able to make around $750,000 in four weeks’ time wagering on college football.

After realizing the potential in the sports betting market, Kutcher became an investor with the eSports company “Unikrn.” In 2017, the company partnered with MGM Resorts International to be able to host events in the Vegas area. When Kutcher bets on sports it’s not because he simply enjoys wagering; he looks at each bet he makes as a business deal and implements all the math and science behind it because that’s his favorite part of the game. Want to know more about the actor turned bettor? Read Ashton Kutcher’s full sports betting bio.

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. While seen as unethical by some, Barkley wagered on the NBA while playing in the league. This was much like Pete Rose, who would bet on the MLB while still being affiliated with the sport. Back in his early sports gambling days, Barkley was still new to the scene so he had not yet set limits for himself. This caused him to lose big and win big but he would often lose three times more than what he would win. He enjoys placing bets on every sport and really loves wagering on championship series’. Barkley has since set limits to the amount 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. He continues to be an avid sports bettor. 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 the better half of the last 20 years and ever since PASPA was repealed, he is more actively betting on sports. 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. He does so well with his sports bets that sportsbooks are kicking him out left and right because they don’t want to lose money to Spanky. Even people who are seen with him are often refused service due to how accurate his calculations are. Learn more about Gadoon Kyrollos and his views on sports betting.