Cynthia Jay Brennan

A California man named Rodolfo T. has won a Megabucks jackpot worth $11.8 million. And what’s interesting is that Rodolfo’s win came on a $3 bet.

Cynthia Jay Brennan grew up in Sacramento with two loving parents and eight siblings (five brothers and three sisters). At a young age she moved away from her family to Las Vegas Nevada and become a cocktail waitress at a local casino, Monte Carlo. This is where she fell in love with Terry Brenna, her now husband. Just weeks before the March 11, 2000, crash, Cynthia Jay-Brennan won a record $35-million Megabucks jackpot. “On one hand we’re happy that he was found guilty on all counts,” Jay-Brennan’s.

  • Cynthia Jay-Brennan – $34.95 Million. As a way to pass some time, Cynthia had a go at a Megabucks slot machine while attending her mother in law’s birthday party. She never realized that by her 9th attempt, she’d manage to win $34.95 million, one of the biggest jackpots for this game at the time.
  • Patricia Demauro. Patricia Demauro holds the record for the most craps rolls without sevening out.
  • Cynthia Jay Brennan She usually was taking on extra shifts in order to get some bonus money because she was planning on marrying her boyfriend. But, the luck was on her side that night when she spun the Megabucks jackpot and won a total of $34,959,458 when all she bet on was a small amount of money.

He was playing the Megabucks slot machine at Vegas’ Fremont Hotel and Casino when his win occurred. He made the maximum $3 wager to ensure that he qualified for the jackpot on IGT’s Megabucks Double 3X4X5X Pay.

Fremont Casino Excited about the Win

Rodolfo T. didn’t offer any statements after winning the massive jackpot. But Fremont Hotel and Casino manager Jim Sullivan spoke with the Daily Mail about his win.

“The Fremont has awarded many thousands of jackpots throughout its 60-year history in Las Vegas. But none quite like this,” said Sullivan.

“We’re incredibly excited to be a part of this amazing jackpot. This furthers Fremont’s longstanding reputation as a place where players win.”

Rodolfo’s Jackpot is a Far Cry from the Megabucks Record

$11.8 million is a lot of money. But it’s still quite a ways off the all-time Megabucks record.

The largest Megabucks win ever is worth $39.7 million. An anonymous software engineer from LA hit this massive prize in 2003.

This is also the biggest slots win in the history of online and land-based casinos. Their win eclipsed the previous Megabucks jackpot record, which was a $35 million win by Cynthia Jay-Brennan in January 2000.

This was quite a story because Jay-Brennan was previously a Las Vegas cocktail waitress.

Unfortunately, Jay-Brennan and her sister were hit by a drunk driver in Vegas just weeks later. She would be left paralyzed for life while her sister would pass away.

This started a rumor that Megabucks winners are cursed, which involved everything from gang murders to suicides.

But none of these other Megabucks tragedies have been proven. Moreover, it’s believed that any Megabucks curse stories beyond Jay-Brennan’s are merely urban legends.

Gambling has a long and interesting history. It’s been a popular activity for almost as long as the human race has existed, and its popularity shows absolutely no signs of slowing down. It continues to be on the up rise: partly because of the consistent improvements in the world of online gambling, and partly because it’s starting to become more socially acceptable.

Throughout its rich history, and right up until today, gambling has attracted an incredible variety of different characters. Some of these individuals are famous (or infamous) for their gambling related exploits. Trust us when we say that their stories make for extremely interesting reading. Actually, that’s why we’ve put together this section of our website, featuring biographies of some of the biggest names in gambling.

When we first started this section we focused on the pioneers and innovators who were instrumental in developing the gambling industry in one way or another. We wanted to include individuals that helped turn Las Vegas into the gambling capital of the world, and those who contributed to the evolution of online gambling. We quickly realized that there were far more stories to tell though, so we decided to expand our scope.

We now have detailed biographies on people involved in all aspects of gambling. We address those who have won big, and those who have lost it all. We’ve written about those who have found legitimate ways to win, those who have cheated and those who have engaged in outright criminal behavior. In short, we’ve covered the good, the bad and everything in between. If there’s a story to tell, we’ve told it.

You can find all our biographies listed on this page. Because there are so many, we’ve divided them into the following categories.

Key Individuals in Online Gambling
Historical Gambling Figures
Gambling Criminals
Blackjack Legends
Professional Gamblers
Land Based Gambling Tycoons
Notorious Gambling Cheats
Poker Players Past & Present
High Stakes Gamblers
Big Gambling Winners

There have been many entrepreneurs and executives who have helped to shape the online gambling industry into a multi-billion dollar enterprise. Many of the big names and important people from the industry could be considered genuine pioneers, and yet they often don’t get the credit they deserve. While many of them have become household names, even more of them are virtual unknowns.

The biographies in this category tell the stories of the people who have turned modern betting and gaming into what it is today. Without them, the evolution of this industry might have been very different. It’s possible that other pioneers would have stepped in to take their place, but realistically gambling sites probably wouldn’t be anywhere near as advanced as they are today.

It wouldn’t be very fun if we focused solely on those who have had a positive impact on the industry though, as the “bad guys” have far more intriguing stories to tell. This small percentage of people are responsible for damaging the industry in one way or another, but their influence is still important to learn about regardless.

Featured Biographies


DENISE COATES

The mastermind behind online gambling giant Bet365


CALVIN AYRE

The charismatic billionaire who founded Bodog


ISAI SCHEINBERG

Innovative but private, he created PokerStars


RUTH PARASOL

The driving force of PartyGaming’s success


THE SHAKED BROTHERS

Founders of 888, one of the best-known gambling sites


ANDREW BLACK

Created Betfair, the most successful betting exchange


RAY BITAR

The main man behind Full Tilt Poker


TEDDY SAGI

Creator of Playtech sports betting software

Additional Biographies

MARK BLANDFORD Founder of SportingBet
SCOTT TOM Absolute Poker Co-Founder
THE BEN-YITZHAK BROTHERS Founder of 888
LEE JONES PokerStars Executive
ROBERT RAATGEVER Microgaming CEO
MICHAEL SHACKLEFORD The Wizard of Odds
VICTOR CHANDLER Founder of BetVictor
JON KARL UltimateBet Co-Founder
VIKRANT BHARGAVA PartyGaming Executive
ANURAG DIKSHIT PartyGaming Executive
GREG PIERSON UltimateBet Co-Founder

Before the online gambling pioneers, the biggest names in the gambling industry mostly consisted of people who built, owned or developed land based casinos. Those names are the inspiration for this category of bios.

Many of the people listed below started small but went on to build huge empires. Some of them had a very significant influence on the way the land-based gambling industry evolved as a whole. Their stories will grab your attention early on and keep you hooked until the very end.

Featured Biographies


BOBBY BALDWIN

President/CEO of Mirage Resorts


JOHN ASPINALL

Bookmaker & founder of the Clermont Club in London


SHELDON ADELSON

Billionaire founder of the Las Vegas Sands Corp.

Cynthia Jay Brennan Nevada


PHIL RUFFIN

Owner of Treasure Island & numerous other casinos


KIRK KERKORIAN

Las Vegas tycoon, the father of the megaresort


STEVE WYNN

Owner of the Bellagio, Wynn Las Vegas, and other venues

Additional Biographies

HOWARD HUGHES Serial Entrepreneur
LIM GOH TUNG Creator of the Genting Highlands
DONALD TRUMP Billionaire casino owner
STANLEY HO Helped develop Macau

In this category we’ve provided bios of some famous historical figures. Although most of these individuals have earned their fame from something other than gambling, gambling has still played a significant role in their lives in one way or another. The diversity of names found here highlights just how widespread the popularity of gambling has always been.

WILD BILL HICKOK
KING HENRY VIII
FYODOR DOSTOYEVSKY
JOHN MONTAGU
CASANOVA
DOC HOLLIDAY
GEORGE E. SMITH

Making money from gambling can be accomplished in one of three ways. The most popular way is to hope that luck is on your side. Another way would be to dedicate a huge chunk of time to learning the various skills and strategies in order to gain an edge over the bookmakers. Either of these approaches would perfectly respectable, although the second is far more likely to yield results.

The third approach is in no way respectable. It’s to cheat, and no one likes a cheater. Actually, when it comes to gambling, that’s not entirely true. Gambling cheats are usually admired by their fellow gamblers: especially when they a share a common enemy (the house). However, no one appreciates a gambler who cheats other gamblers. That’s wrong on so many levels.

The gamblers found on the list below are well known for their cheating exploits. We don’t doubt that this list would be bigger if it weren’t for the gambling cheats who were successful and gotten away with it. As much as we’d love to know THOSE stories, we probably never will.

All Biographies

RON HARRIS Rogue Employee
TOMMY GLENN CARMICHAEL Slot Machine Cheat
RICHARD MARCUS Inventor of “The Savannah”
LOUIS COLAVECCHIO Largest Lottery Token Cheat Ever
IDA SUMMERS The “Vegas Vixen”
DENNIS NICKRASCH Slot Machine Cheat
MONIQUE LAURENT Famous Roulette Cheat
TRAN ORGANIZATION Bribed Casino Dealers

Gambling and criminals basically went hand in hand at various points in history. At times, gambling was considered an “underground” activity run by criminals. Nowadays, in general, things have changed for the better. With so much money involved in gambling, however, one might suspect that some gambling-related crimes still go on today.

In this category we’ve provided bios on some of the most interesting criminals involved in some sort of gambling scandal.

Featured Biographies


JESSE JAMES

Infamous American Outlaw and gambler


BUGSY SIEGEL

Feared mobster and casino owner

Additional Biographies

BUMPY JOHNSON Mob Boss and Bookmaker
BRIAN MOLONY Embezzled millions
DANIEL TZVETKOFF Violated the UIGEA
ARNOLD ROTHSTEIN Kingpin of the Jewish Mob
HERBERT BLITZSTEIN Loanshark & bookmaker
GEORGE FREEMAN Links to Illegal Bookmaking
Cynthia Jay Brennan

Poker could easily be considered one of most popular forms of gambling in the world. It has many appealing characteristics, and it strikes a good balance between luck and skill. Players with no skill at all can get lucky and beat much better players on occasion, but the truly skilled players almost always make money in the long run.

The general interest in poker is so widespread these days that successful poker players are genuine celebrities. Televised tournaments and cash games attract huge audiences, and it’s not just because people enjoy watching other people play cards. They enjoy watching how the characters at the table interact too, especially the big name players.

It’s the big name players that you’ll find here. We’ve compiled biographies on the best-known players: past and present. If you have aspirations of becoming a successful player yourself, then it wouldn’t hurt to thoroughly read these biographies in order to see what it takes to make it to the top.

Featured Biographies


PHIL IVEY

One of the best poker players of all time


PHIL HELLMUTH

Extremely successful player known as “The Poker Brat”


DAN BILZERIAN

Poker playing playboy known as “The Blitz”


CHRIS MONEYMAKER

Won the WSOP main event after qualifying online


DANIEL NEGREANU

Charismatic and popular professional poker player


VANESSA ROUSSO

One of the most successful female poker players

Additional Biographies

Tom Dwan
Chris Ferguson
Gus Hansen
Jennifer Harman
Phil Laak
Erick Lindgren
Doyle Brunson
Brian Townsend
John Juanda
Annie Duke
Andy Bloch
Barry Greenstein
Danial Cates
Alan Schoonmaker
Jamie Gold
Barny Boatman

No casino game has ever captured the attention of so many quite like blackjack has. This relatively simple card game is intriguing on many levels, and it also happens to be the only casino game that can be genuinely beaten without resorting to cheating. A skilled blackjack player can actually gain an edge over the house by counting cards.

Advantage players have shown a strong interest in card counting for several decades now. Some skilled card counters are considered true legends for their contributions to the subject, while others have earned that title thanks to their exploits in the casino. Learn more about all these interesting characters by reading the following biographies.


KEITH TAFT

Bona-fide genius and successful counter


Las Vegas Megabucks

EDWARD THORP

Established Author and “the godfather of card counting”


KEN USTON

Successfully sued a casino for banning him


TOMMY HYLAND

Manager of the longest running counting team

Additional Biographies

MIT BLACKJACK TEAM
STANFORD WONG
JAMES GROSJEAN
THE FOUR HORSEMAN
AL FRANCESCO
IAN ANDERSEN
DARRYL PURPOSE
JULIAN BRAUN
ROBERT NERSESIAN
JOHN CHANG
DON SCHLESINGER

For some, the thrill of gambling is simply not enough. These people only want to gamble if they have the opportunity to win big. It’s easy to relate, as gambling obviously becomes more exciting when there’s more at stake. For the majority of us, though, our idea of big stakes may just be a few more dollars than we usually bet.

The guys listed below are on a whole different level. They are (or were) REAL high-rollers. They have gambled millions upon millions of dollars, often risking sums that most people would consider to be a fortune on single wagers.

Featured Biographies


KERRY PACKER

Media tycoon who loved to gamble for big money


WILLIAM LEE BERGSTROM

Placed some of the largest ever bets in casinos


ARCHIE KARAS

A famous gambler who went from rags to riches


NICK DANDOLOS

Won and lost huge sums of money while gambling

Professional Gamblers

For most people, gambling is nothing more than a fun activity to enjoy with friends. For a small percentage of gamblers, however, it’s a lot more than that. Professional gamblers, or those who have decided to make gambling their career, are obviously very good at what they do. Many of them also live very interesting lives.

As you might imagine, a lot of professional gamblers are very secretive. They don’t want everyone knowing how they do what they do. Nonetheless, we’ve managed to compile a few bios on some of the more colorful characters that gamble for a living.

Additional Biographies

Barney Curley
Clive Holt
Sidney Harris
Jack Ramsden
Phil Bull
Bill Benter
Barry Meadow
Alan Woods

Most gamblers appreciate a win of any kind. We all hope to win big, of course, but even just a small win is better than no win at all. And there’s always next time, when maybe we’ll finally get that elusive win that will really change our lives. This might be based more on hope than expectation, but that’s partially what makes gambling so much fun.

The people below help reassure us that our dreams can indeed come true. These are among some of the biggest gambling winners of all times. If it can happen to them, it can happen to any one of us. Right?

Gonzalo Garcia-Pelayo

Gonzalo Garcia-Pelayo is one of the most successful roulette players of all time. He’s considered by many to be the first person to truly exploit the bias that mechanical roulette wheels can show. He invested months of his life to studying and analyzing the behavior of wheels in Spain, before winning hundreds of thousands of dollars based on his findings.

Elmer Sherwin

Slots players all over the world share the dream of one day hitting a big jackpot. A select few of them will get lucky and realize their dreams, but we doubt than anyone will ever be as lucky as Elmer Sherwin. Why would we make such an assumption? Well, it’s because he won the Megabucks Jackpot not once, but twice. He won $4.6 million in 1989, before following that up with another $21 million win 16 years later. This is a truly unbelievable story.

Conor Murphy

Conor Murphy is an inspiration to horse racing bettors. He proved that it IS possible to win big, providing you bid your time and wait for the right opportunities. His opportunity came in 2011, while working as a horse racing trainer. He identified five horses that he felt would do well in the following year’s Cheltenham Festival, and placed an accumulator accordingly. All five won, bringing him in over $1 million.

Charlie Wells

There is a great deal of uncertainty over exactly how Charlie Wells landed his big win, but some facts are known for sure. In the late 19th century, he made two trips to the Monte Carlo Casino and won the equivalent of $10 million in today’s money. This was all from roulette. He claimed to have a system, but it’s been speculated that he cheated. Maybe he just got lucky. Whatever the truth may be, he’ll always be known as the man who broke the bank at Monte Carlo.

Colin & Chris Weir

This married couple from Scotland made the headlines back in 2011 when they won the lottery. Although simply winning the lottery isn’t extraordinary, how much they won was. They won £161 million (around $240 million) to be precise. This was the highest amount ever won in the United Kingdom: an astonishing amount of money from a ticket that cost only £2.

Ashley Revell

They say you have to be prepared to take big risks to win big. It’s hard to imagine anyone has ever taken this more literally than Ashley Revell did. In 2004 he sold all his possessions, and travelled from England to Las Vegas. He put everything he had ($135,300) on a single spin of the roulette wheel. He bet red, and got extremely lucky.

Cynthia Jay-Brennan

Cynthia Jay-Brennan is another Megabucks Jackpot winner. She won $35 million in 2000, which was a record at the time. This is a story in its own right, but what happened subsequently highlights just how cruel life can be. Just a few weeks after her record win, she was involved in a car accident and paralyzed from the chest down.

Gloria MacKenzie

Gloria MacKenzie won the Powerball lottery in 2013. This wasn’t just any Powerball lottery. She won the largest undivided prize in its history, a cool $590 million. She could have had the full amount paid over 30 years, but she opted from the lump payment of $370 million. At 84 years old, we don’t think anyone could blame her for this decision!

Don Johnson

No, not the actor. This Don Johnson is a professional gambler who went on one of the most astonishing winning streaks ever known. During a six-month period in 2011, he took Atlantic City casinos for over $15 million. He played only blackjack, and managed to convince the casinos to change some of the game rules to his favor. This obviously helped, but he still needed a great deal of luck to win that big.