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From TV Games to Vegas Jackpots – These are America’s Biggest Winners in History

Legendary Yankees pitcher Lefty Gomez coined the phrase that it’s better to be lucky than good. It’s a great soundbite, although it doesn’t stand up to close scrutiny under every circumstance. One thing is certain, however, America’s biggest prize winners could certainly identify with Lefty’s words. From the Game Show Network studios at Culver City to the casinos of Las Vegas, let’s meet some of the luckiest winners in American history.

Edwin Castro lucked his way onto Billionaire’s Row

We will start with someone who has a reasonable claim to the “luckiest man in the world” label. In February 2023, the California Lottery confirmed that Edwin Castro had defied odds of almost one in 300 million to claim a record Powerball jackpot of just over $2 billion.

Mr Castro bought his lucky ticket for $2.00 at his local gas station, Joe’s Service Center, in Altadena, to the north east of Los Angeles. Proprietor Joe Chahayed was also counting his luck – he won $1 million just for selling the winning ticket!

California Lottery tickets are sold on the understanding that the organizers will disclose the names of winners. However, Mr Castro has done his best to keep a low profile since the win, declining to attend the press announcement and issuing only a brief statement.

He has, however, already spent $25 million of his winnings on a mansion in the Hollywood Hills. The five-bedroom property includes a wine cellar, movie theater, bar, games room, fitness studio and dry sauna, as well as a showroom with space for five cars.

Megabucks – the most appropriately named casino slot

Jackpot slot games provide the opportunity to win sums that are right up there in lotto territory – and at similarly long odds. The way it works is that multiple interconnected machines contribute a little more to a progressive bonus with every bet that’s placed. It keeps going up and up until – someone gets lucky. Progressive bonuses can easily run into the millions, and in these days of online slots, there are more games like this than ever. The Legit Gambling Sites page at will tell you more about the different jackpot slots games that US players can try online.

The best-known jackpot slot is Megabucks, and it is also responsible for the two biggest slot wins in US history. Back in 2000, a cocktail waitress called Cynthia Jay-Brennan won just under $35 million on a Megabucks machine at the legendary Desert Inn, just months before it closed for good. Hers was a tragic story, as just a few weeks later, she was involved in a car accident that claimed her sister’s life and left Cynthia paralyzed.

Three years later, Cynthia’s record was broken by a 24 year old software engineer. He chose to remain anonymous, but we know he won $39.7 million on the back of a $100 spin of the reels.

Megabucks might sound like a great way to get rich, but the odds are actually even longer than Edwin Castro’s lottery win. Keep in mind that hundreds, perhaps thousands of people play Megabucks every day – but that $39.7 million jackpot record has remained in place for 20 years and counting.

Skill plus luck can be the ideal formula

TV gameshows rely on a mixture of skill and luck in varying degrees. Ken Jennings has won more than $5 million on TV. He’s shown some solid skill in answering questions over the years, but has had some moments of good fortune, too.

Ken is, of course, most famous for his 70-game winning streak on Jeopardy, a show he later went on to host. His winning streak spanned the 20th and 21st seasons of the show, but good fortune prevented him from crashing and burning in the first episode of the new season. Asked to name the first female track & field athlete to win medals in five different events at a single Olympics, Ken’s answer of Jones would usually be insufficient, as forename and surname are usually required. However, Alex Trebek accepted the “half answer” and Ken’s run continued. The full answer, in case you were wondering, was US athlete Marion Jones.

That was one of very few narrow squeaks for Ken, and it would sound like sour grapes to say his success was all down to luck after that one potential banana skin was successfully negotiated. His record run won him a total of $2.7 million. However, with return visits, including a $1 million face-off against long term rival Brad Rutter, his total winnings are well over $5 million.

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