Lottery Winners: The Top 5 All-Time List

Jacob Rebb

Lottery Winners List

When thinking about playing and winning the lottery, most people look at their chances of winning as likely as getting struck by lightning. However, there are a lucky chosen few lottery winners who have hit it big more than once (one person even 14 times). Let’s dive into some of the most memorable multiple-time lottery winners. 

5. Lightning can strike twice 

Imagine this. You walk into your local corner store with a few crumbled dollars in your pocket and decide to try your luck at a scratch-off ticket. You walk out the door, start scratching, then boom, you are $10 million richer. That’s what happened to Juan Hernandez of New York. In 2019, Hernandez won $10 million on the popular scratch-off game, the $350 million Cash Spectacular. His life was changed forever. 

That’s not the end of Hernandez’s story, though. Hernandez did the (nearly) impossible and hit it big on yet another scratch-off. I guess when you have $10 million, you might be able to buy a few extra scratch-off tickets than usual. So, when Hernandez scratched off this ticket, you can imagine his surprise when he won the top prize, another $10 million. For his prize, he took the lump sum offer of $6,510,000. He said he was still trying to spend his first prize. 

4. The best mistake ever made 

Virginia resident William Newell had played the lottery for most of his life. He was known to his local convenience store as the guy who always played Pick 4, but something different happened this time for the old-school lotto player. 

On this day, Newell decided to stay home and try out the new online lottery available through the Virginia State Lottery. It was early in 2021, and with gambling becoming more widely accepted across the country, states were upgrading their antiquated lotto systems, Virginia being one of them.

So, Newell went onto the new lottery app, and instead of purchasing just one Pick 4, he purchased 20, all of the same numbers (5-4-1-1). Buying the same ticket more than once does not improve your chances of winning, but if you do hit, each ticket pays out the full prize amount. 

So, the Pick 4 drawing happened, and Newell hit all four numbers. Each ticket won the full prize amount, $5,000 each, totaling a grand prize total of $100,000. The retired Virginia resident said he doesn’t have plans for his winnings, but “It feels good, no doubt about it!”

3. An oldie but a goodie 

This story comes from more than 40 years ago. In the mid-1980s, a trailer park resident, Evelyn Adams, wasn’t in the greatest financial situation. She was worried her spending habits on the lottery were getting out of control as she would spend upwards of $100 per week on lottery tickets, which was a lot of money in the ‘80s. She was a convenience store worker, so it was difficult for her to avoid. 

Luckily for Adams, her dedication to playing paid off when she finally hit the big one and nailed a multiple-million-dollar winner. Of course, now that she won, why would she stop playing? So, four months later, as Adams went to check her tickets, she struck it big again. Her total winnings in that four-month span were $5.2 million. 

Unfortunately for Adams, she said years later that she had lost most of the $5.2 million in winnings on slot machines in Atlantic City. 

2. Re-enactment leads to second big win 

It’s June 1998, and Australian truck driver Bill Morgan almost died from a major heart attack that left him in a coma for more than two weeks in a Melbourne hospital. When Morgan woke up, he felt like he was the luckiest man alive since he survived his heart attack and coma. When he left the hospital, Morgan tried his luck at a local store and won a brand-new car. He couldn’t believe it.

The local news station heard about Morgan’s survival story and winning the lottery. The news decided to do a story on his luck, and they asked him to return to the store where he won the car. To re-enact his original win, he bought another lotto ticket. While filming this re-enactment, Morgan realized he had actually won an additional $250,000 on the ticket he bought to do the re-enactment. 

From heart attack and comatose to cruising in a new car with a big bag of cash. It seems like life got better for Bill Morgan. 

1. Jerry and Marge Go Large 

One of the best-known stories to hit the lottery was that of Jerry and Marge Selbee. In 2003, Jerry Selbee, a recent retiree in Michigan, saw something interesting in a game called Winfall. A math whiz his whole life, Selbee quickly saw a loophole in the Winfall game after reading the game brochure in his local convenience store. 

By exploiting this loophole, Jerry and his wife, Marge, started to win a lot. They even created a business in which they sold shares to family and friends, now that they were betting hundreds of thousands per game. At its peak, their “investment” company, G.S. Investment Strategies, had 25 members.

The same game then opened in Massachussets, where they continued their operation. G.S. Investment Strategies played Winfall in Michigan 12 times, winning over $2.6 million. They played the Winfall game in Massachusetts 43 times, winning more than $24 million in prizes. 

This incredible story was later made into a movie starring Bryan Cranston and Annette Bening called Jerry and Marge Go Large. The couple only lost money on three out of the 55 drawings where they participated.

You Can’t Win If You Don’t Play 

There we have it — the top five most memorable multiple-time lotto winners. From trailer park winners to heart attack survivors, we see the lotto has no favorites. It strikes at random, changing lives one win at a time.