Check out this list of strange and whacky ways Powerball winners have spent their prizes, from waterparks to theaters.
You won the Powerball jackpot. What would you do? Many would fantasize about mega mansions, Lamborghinis, and world-jetting vacations. But some other winners take stranger paths with their spending. These are actual (and a few whacky) Powerball stories about things that people actually purchased with their winnings. It’s weirder than you would think.
When Edwin Castro claimed the record-setting $2.04 billion Powerball jackpot in 2022, headlines focused on his Hollywood Hills mansion. (Ok, so he did buy the mansion.) But what he did next was far more unusual.
Instead of chasing more luxury, Castro quietly began buying fire-ravaged plots of land in his hometown of Altadena, California, properties damaged during the 2025 Eaton Fire. Reports suggest he’s spending around $10 million to rebuild the neighborhood, saying his goal isn’t to flip homes for profit but to help families return to their community.
It’s part philanthropy, part long-term investment, and completely opposite of the typical “new toys” spree. For someone who could have gone full billionaire mode, Castro’s decision feels almost radical in its restraint.
At just 19, South Carolina’s Jonathan Vargas won $35.3 million and decided to chase a teenage dream instead of a Ferrari.
He created Wrestlicious, a women’s professional wrestling TV show blending athleticism, sketch comedy, and campy storylines. It aired briefly in 2010 before folding, but Vargas had already done what most only talk about: turned fantasy into reality.
Critics called it bizarre. Fans called it fun. Either way, it was funded entirely by his Powerball win. Not bad for a kid who went from gas station regular to TV producer before his 20s.
When Jack Whittaker, a West Virginia contractor, hit $314.9 million in 2002, he became a national sensation, then a cautionary tale.
Whittaker took a lump sum of $113 million after taxes and immediately started handing it out. He gave away houses, cars, and wads of cash to strangers, waitresses, churches, and anyone who asked.
He famously drove around with suitcases of cash in his car and dropped thousands into donation plates. But generosity came with chaos. He was robbed multiple times, his personal life unraveled, and tragedy followed.
His story is as fascinating as it is haunting, proof that sudden fortune can magnify both kindness and vulnerability.
In 2014, former monk Roy Cockrum of Tennessee won $259.8 million and made one of the most quietly remarkable moves on this list.
Instead of living lavishly, he founded a charitable foundation to support nonprofit theatre productions across America. A one-time actor and spiritual devotee, Cockrum turned his win into a mission for the arts, underwriting plays and giving grants to creative projects that might never have seen a stage.
No islands. No sports teams. Just art, faith, and a belief that storytelling changes lives.
In 1999, Timothy Schultz, a 21-year-old gas station attendant from Iowa, won $28 million. His first splurge? A video-game console.
Then he invested the rest, went back to school, and eventually launched a podcast where he interviews other lottery winners. Schultz is still known today for being unusually level-headed about sudden wealth, a man who learned early that the jackpot doesn’t fix your life, it just amplifies it.
Winning changes your options, but it doesn’t determine your path. These Powerball stories prove that money doesn’t just buy things; it reveals priorities.Some winners chase nostalgia. Some chase impact. Some chase chaos. Each story has a pulse: a person suddenly holding more power than they imagined, deciding what kind of story they want to tell next.
If you ever found yourself in that “what now?” moment, maybe the sharper question isn’t what will I buy? But who will I become?
So, what would you do if you hit the Powerball?Would you build something for others? Start something wild? Or slow down long enough to find your next purpose?