The Biggest Casino Winners in History: Where Are They Now?

Las Vegas Slots. (Image:
Las Vegas Slots. (Image:

We are always hearing about lottery winners and how they spend their winnings. When someone wins the lottery, he or she is plastered all over the news right after it happens, and then again a year later or so as an update on how their lives are going.

The media gives lottery winners a lot of attention because we as a society are incredibly curious about them. What were their lives like before they won? Do they deserve the money? What are they doing with the money? Are they spending it wisely?

Many people do not really realize that casino winners sometimes win just as much money as lottery winners do. Gamblers have unexpectedly won millions and millions of dollars by playing slots, craps, blackjack, roulette, and other games at casinos, both online and offline.

Let’s talk about three lucky ducks who have hit it big and instantly became high rollers at casinos all over the world. What were their lives like before they won? What did they do with the money? Where are they now? Let’s find out!

1. Cynthia Jay Brennan / $34,959,458.56 / Las Vegas, NV / 2000

In 2000, Cynthia Jay Brennan, a cocktail waitress, became one of the luckiest people in the world when she won the largest Megabucks jackpot in history at the time. She was playing a state-wide lottery jackpot slot machine called Megabucks in Las Vegas when she struck it big and won $34,959,458.56. The next nine weeks were wonderful for her. She celebrated her good luck, married her boyfriend, and was planning on traveling the world with him.

Unfortunately, nine weeks after she won $35 million, Cynthia was driving her new Camaro with her sister, Lela Jay, when a drunk driver with 16 prior arrests slammed into her car at a red light. Lela was killed right away, and Cynthia’s spine was shattered. The driver walked away with just a few scratches.

Today, Cynthia is paralyzed from the waist down and uses a wheelchair. She can only move her arms and shoulders, and she requires assistance to do the simplest of tasks like brushing her hair and dressing herself. Her husband, Terry Brennan, is still working as a bartender at the Monte Carlo Casino in Las Vegas and is taking care of his paralyzed wife.

Cynthia says she’d give the $35 million back if it meant walking again and getting her sister back.

2. Ashley Revell / $270,000 / Las Vegas, NV / 2004

Ashley Revell’s story is pretty interesting. Ashley was hanging out with his friends at a pub when one of them commented on how great it would be if they could bet everything they had on one spin. So Ashley did just that… and won.

Ashley was a 32-year-old man from London, England with a Rolex watch, a BMW, golf clubs, and 10,000 pounds to his name. He sold all, and we mean all, of his possessions at car boot sales and auctions and then headed over to the Plaza Hotel & Casino in Las Vegas with only the clothes on his back and nearly 80,000 pounds to his name to place his one bet at a roulette table.

Ashley was originally supposed to place his bet at the Hard Rock Hotel, but negotiations with the hotel’s management fell through. Plaza Hotel & Casino stepped in and accepted the wager because they were looking for a lot of publicity. They offered Ashley a free suite room and a special roulette table where the bet could be videotaped and broadcast live through the Sky Network.

At first, Ashley couldn’t decide whether to bet on red or black. He came to decide on black, but a lot of his supporters preferred red, so Ashley switched over to red at the very last minute. It was the right choice, because the ball landed on number seven… red!

Everyone, including Ashley’s family and friends, cheered and popped open a bottle of champagne. His stack went from nearly 80,000 pounds to 153,680 pounds.

He celebrated his win by going on a trip around Europe on the back of a motorcycle. When he was in Holland, he met his future wife. When he came back home, he set up an online poker company named Poker UTD (which eventually went out of business in 2012) and later established iGaming Recruitment, a website that matches job applicants to online gambling companies.

So what does Ashley’s life look like now?

He does not gravitate towards the flashy lifestyle. He’s still an ordinary guy who drinks at the pub over the road, manages his business, and hangs out with his wife and two children.

Elmer Sherwin / $21,147,947 / Las Vegas, NV / 2005

Elmer Sherwin was probably the luckiest man in Las Vegas. He was a two-time Megabucks winner. In 1989, he won $4.6 million right after the Mirage opened on the Las Vegas Strip.

On an early Thursday evening in September 2005, 92-year-old Elmer Sherwin, a World War 2 vet, decided to plop down in front of a Megabucks machine at the Cannery Casino & Hotel in Las Vegas because he had a feeling that the machine was lucky. Well, he was right because he won the $21,147,947 jackpot.

With that money, Elmer donated a lot to the Hurricane Katrina relief fund and helped support his family, including his son and daughter-in-law.

Elmer passed away two years later, in March 2007.