Infamous Gamblers: 10 Notorious Betting Legends Who Broke the Law
Introduction: When Gambling Crosses the Line
Gambling has long attracted bold personalities, risk-takers, and sometimes, those willing to test the boundaries between luck and legality. While most gamblers simply seek entertainment or the thrill of the win, history has seen its share of notorious figures who landed on the wrong side of the law. From insider trading to elaborate heists and shocking scandals, the following ten gamblers didn’t just place bets—they crossed legal lines and paid the price. Discover their stories below.
1. Dan Bilzerian: Explosives and Outrage
Known as the “King of Instagram,” Dan Bilzerian carved a name for himself through high-stakes poker, a lavish lifestyle, and a massive social media following of over 32 million. Whether it’s showing off his collection of firearms, celebrity friends, or unusual pets (such as goats), Bilzerian is always in the spotlight.
Bilzerian has dodged legal repercussions for several alleged incidents, including reports of assault during a nightclub scuffle and a bizarre rooftop stunt that left a model injured. However, it was an arrest at LAX for possessing bomb-making materials that finally landed him in legal trouble. Authorities linked him to detonating an explosive-laden cooler, resulting in a massive blast. Despite the severity, Bilzerian spent less than a day in custody and resolved the matter with a fine.
2. Mike Matusow: Drug Dealing at the Poker Table
Mike Matusow, nicknamed “The Mouth” for his colorful trash talk, is a poker phenom with four World Series of Poker (WSOP) bracelets and a reputation for dramatic emotional outbursts. However, his problems expanded beyond the felt.
Caught in a police sting, Matusow supplied an undercover officer with prescription painkillers and ecstasy. The result was a six-month stint behind bars in 2004-2005—a sobering chapter in the career of one of poker’s most outspoken players.
3. Dragan Kostic: Tax Evasion on Tournament Winnings
Dragan Kostic, a native of Macedonia based in Spain, gained recognition with a runner-up finish at the EPT Barcelona Main Event, bagging €532,000. However, his windfall brought major trouble with Spanish authorities.
Kostic failed to declare his considerable winnings on his tax returns. Inevitably, the authorities responded with an 18-month jail sentence and hefty fines. Despite repeated appeals, the punishment remained in place—a costly oversight for the poker pro.
4. Billy Walters: Sports Betting King and Insider Trading
Billy Walters is revered on the Vegas Strip for his legendary sports betting prowess. Once rumored to own seven homes and command a fortune exceeding $100 million, Walters didn’t confine his risk-taking to the casino.
In 2017, Walters was convicted of orchestrating an insider trading operation estimated to have netted him $32 million. The penalty was severe: five years imprisonment and a $10 million fine. Walters also faced previous indictments for illegal bookmaking but managed acquittals in earlier trials. Due to the Covid-19 pandemic, his sentence shifted to home confinement, set to last until 2022.
5. Tony O’Reilly: Stolen Millions from the Post Office
Irish post office manager Tony O’Reilly is a stark reminder that gambling addiction knows no boundaries. Battling overwhelming debts, O’Reilly embezzled €1.75 million from his rural post office, starting with coin bags and eventually pilfering bundles of cash.
The authorities caught up with him in 2011. Sentenced to three years in prison, he served 18 months before release. O’Reilly publicly documented his journey to recovery in a book, with proceeds supporting charitable causes.
6. Ted Forrest: Felony Charges Over Bounced Casino Checks
Ted Forrest, a six-time WSOP champion with a World Poker Tour title to his name, ran afoul of the law in 2016. Forrest was charged with felony theft after writing two bad checks to Wynn Las Vegas, totaling $215,000—a serious offense in the casino world.
The bounced checks led to both criminal and financial consequences, marking a dramatic turn in Forrest’s accomplished poker career.
7. Dan Tan: Global Match-Fixing Mastermind
Singaporean high-roller Dan Tan (Tan Seet Eng) is notorious for his role in the massive “Calcio Scommesse” soccer match-fixing scandal of 2011. Dubbed the “Kelong King,” Tan was considered the ringleader in a criminal enterprise that fixed over 150 matches across Europe and Nigeria.
Tan was convicted and spent nearly six years behind bars, following previous incarceration for illegal betting in the 1990s. His criminal activity shook the sports world—and highlighted the vast networks behind illegal gambling.
8. Ernie Scherer III: Poker Pro Turned Murderer
Ernie Scherer III was already a successful US poker pro, earning over $300,000 in tournaments. But in a chilling twist, Scherer was convicted in 2011 for the brutal murder of his parents in 2008, orchestrating the scene to look like a home invasion.
Investigators determined that financial motive drove the crime; Scherer—deep in debt and facing losses—was eager to claim his looming $2 million inheritance. He ultimately received two life terms for the shocking murders.
9. Bryan Micon: Operating an Unlicensed Bitcoin Poker Site
Bryan Micon was a pioneering poker player and operator of ‘SealsWithClubs’, one of the first bitcoin-based poker sites. However, his platform operated as an unregulated casino in the tightly controlled gaming state of Nevada.
Facing prosecution for illegally running a gaming business, Micon fled to Antigua. He returned in 2015 to accept a plea deal: probation, a $25,000 fine, and additional penalties, narrowly escaping a decade-long prison sentence.
10. Peter Jepsen: High-Tech Cheating at the Poker Table
Danish poker professional and ex-military police officer Peter Jepsen made headlines with record-breaking online poker winnings. Yet, his later exploits veered far from fair play.
In 2019, Jepsen received a three-to-four-year prison sentence for an elaborate cheating scheme which involved hacking fellow players’ laptops during international poker tournaments. Authorities believe the scam netted at least €3.5 million between 2008 and 2014. Jepsen is currently appealing his decision—but the magnitude of the crime stunned the poker world.
Conclusion: The Dark Side of High-Stakes Gambling
From insider trading and match-fixing to high-tech scams and even murder, these cases reveal the extremes to which some gamblers will go. While casinos and card rooms can offer excitement and opportunity, they can also become the backdrop for scandalous falls from grace when risk-taking replaces all sense of legality and morality.
Fascinated by crime and punishment? Explore our interactive feature on the odds of escaping prison in your state for more tales of high-stakes risk and consequence.
