Powerball Winners Who Made Headlines for the Strangest Reasons

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  • Author:
    Shaun Greer
  • Published:
    29/04/2025

Powerball winner stories are thrilling and exciting. But for these winners, their circumstances put them back in the headlines for even more dramatic reasons.

For Powerball jackpot winners, there’s usually a little time in the limelight with local headlines about the life-changing win. And for massive jackpot prizes, winners garner national attention. But what happens next? For these few Powerball winner stories, we’ll share how some winners made the headlines again and for the strangest reasons.

The Philanthropist’s Downfall

When generous businessman Andrew Whittaker from West Virginia won $314.9 million in 2002, he pledged 10% of his winnings to Christian charities and established the Jack Whittaker Foundation to aid low-income families. But his cash-infused life soon took another, tumultuous turn. Whittaker made headlines again as his wife left him, he lost his Virginia home to a fire, he fell victim to theft, and faced countless lawsuits. He later admitted that he felt winning the Powerball jackpot had been a curse for him.

The Record-Breaking Winner’s Legal Battle

When Edwin Castro from California won a jaw-dropping $2.04 billion Powerball jackpot in November of 2022, he opted for a lump-sum payment of $997.6 million. But Castro’s newfound wealth soon led to a bitter legal dispute when a man claimed the winning ticket had been stolen from him. The court ultimately sided with Castro.

The Man Who Almost Lost His Win

Timothy Schultz, a gas station worker from Iowa, won a $29 million jackpot in 1999. But his celebration was cut short when he briefly lost the winning ticket! Adding to the chaos, a teenage coworker who had sold him the ticket tried to claim a portion of the winnings. Ultimately, Schultz was declared the rightful winner, and today, he helps other Powerball winners navigate sudden wealth on his YouTube channel.

The Winner Who Was Denied His Prize

In 2023, Washington, D.C. resident John Cheeks thought he won a $340 million Powerball jackpot. After all, his ticket matched the numbers online. But when he attempted to claim his prize, lottery officials repeatedly denied the win, stating the numbers posted online were a mistake. Determined to collect his winnings, Cheeks filed a lawsuit against the Powerball lottery. As of now, the case is still pending.

The Unemployed Ex-Con Who Won Millions

In 2001, ex-con David Lee Edwards was unemployed and living with his parents in Florida when he won a one-fourth share of a $280 million Powerball jackpot. He took a lump sum payment of $41 million and banked $27 million after taxes. After lavishly spending nearly half his fortune, his life began to spiral out of control due to escalating drug use. He eventually lost his mansion and died nearly penniless in hospice.

The Lottery Winner Turned Bank Robber

In November 2007, Timothy Elliott, a 55-year-old Massachusetts resident, won a $1 million lottery prize. This win was controversial because Elliott was on probation for (ironically) a 2006 unarmed bank robbery and was prohibited from gambling. Despite violating his probation by purchasing the lottery ticket, a judge ultimately allowed him to keep his winnings, with one caveat. He was required to pay a monthly probation supervisory fee.

The Family Feud Over Millions

North Carolina woman Marie Holmes won a $188 million Powerball jackpot in 2015, but her prize led to drama and legal troubles. She spent millions bailing out her boyfriend multiple times and faced lawsuits from family members and a pastor who claimed she had promised to donate winnings to his church. The chaos surrounding her spending habits and legal battles has made her one of the most controversial lottery winners in recent history.

From scandalous legal battles to reckless spending, these Powerball winners prove that hitting the jackpot doesn’t always mean a happily ever after. While dreaming big is part of the fun, it's just as important to plan wisely, make informed decisions, and seek professional guidance when managing a major windfall. Whether you're playing for fun or hoping for a life-changing prize, always remember to play responsibly—and if you do hit it big, spend responsibly, too!