Big Wins
The jackpots and the improbable runs that made headlines, told with the numbers intact.
26 entries. Latest shelved 24 Aug 2026.
- BW·J649
Johanna Huendl's $22 Million Bally's Megabucks Jackpot
On March 21, 1997, Johanna Huendl won $22.6 million on a Bally's Megabucks machine in Las Vegas, setting a record. The mathematics behind progressive slots reveals why jackpots hit so rarely.
By Play Trump Casino Reading Room
- BC·P445
Phil Ivey vs Crockfords: The 7.7M Pound Baccarat Case
September 2012. A world-class poker player walked into a high-limit baccarat room in London with a specific advantage. What followed was the most contentious legal battle in modern casino history.
By Play Trump Casino Reading Room
- BW·B439
The Biggest Sports Betting Wins in Recorded History
From the $600M Mega Millions of parlay cards to the Serbian bettor who turned $100 into $440K on a single Premier League weekend: the people who beat impossible odds and what they bought with the money.
By Play Trump Casino Reading Room
- BW·F462
The Finnish Player Who Won 24M Euros on Mega Fortune
June 2013. A Finnish player won 24 million euros on a Mega Fortune progressive slot. It was the largest slot jackpot in history at that time. The win was legitimate. What made it interesting was what happened after.
By Play Trump Casino Reading Room
- BW·R876
Russ Hamilton and the Biggest Online Poker Cheating Scandal
Russ Hamilton was a founding player of the World Series of Poker. In 2001, he was caught running a bot ring and stealing accounts from PartyPoker. It was the biggest cheating scandal in online poker history.
By Play Trump Casino Reading Room
- BW·S669
What to Do When a Sportsbook Limits Your Account
A sportsbook just cut your maximum bet from $500 to $50. This happens to winners. Here's what it means and what you can do.
By Play Trump Casino Reading Room
- BW·B793
Bryn Kenney: Inside the All-Time Poker Money Leader
Bryn Kenney. The name carries weight in rooms where real money sits on felt. A kid from New York with an instinct for blood in the water. By 2024, he had moved more chips than anyone alive.
By Play Trump Casino Reading Room
- BW·C961A
Cynthia Jay-Brennan: The Tragic Story Behind a $35M Slot Win
On January 26, 2000, Cynthia Jay, a 37-year-old cocktail waitress at Monte Carlo Casino in Las Vegas, hit the Megabucks progressive jackpot for $34,959,458. Six weeks later, a drunk driver struck the car she and her sister were riding in. Her sister died. Jay was left a paraplegic.
By Play Trump Casino Reading Room
- BW·I749
Isildur1 vs the Online Poker Elite: Viktor Blom's Rise
Viktor Blom played online poker under the handle Isildur1. He was young, aggressive, and fearless. In 2009-2010, he won and lost tens of millions of dollars in high-stakes games. His story is a case study in youth, talent, and the limits of both.
By Play Trump Casino Reading Room
- BW·P652
What Is a Poker Rakeback?
Rakeback is money the sportsbook gives back to players. The first time most poker players hear about it, they've already lost thousands without it.
By Play Trump Casino Reading Room
- BW·C961
Cynthia Jay-Brennan: The Tragic Story Behind a $35M Slot Win
In 2000, Cynthia Jay-Brennan won $34.9 million at a Las Vegas slot machine. Four years later, she was dead.
By Play Trump Casino Reading Room