Lottery Winners Who Lost It All: 5 True Stories and the Money Lessons

Tonight’s Powerball drawing (10:59 PM ET) is worth an estimated $485 million — or $199.8 million in cash — after nobody won Monday’s draw. Millions of tickets are in play, and every one of them carries the same daydream: what would I do with all that money?

But there’s a quieter side to winning that rarely makes the celebration headlines. Some of America’s most famous lottery winners ended up broke, bankrupt, or worse — and their stories are among the best-documented cautionary tales in personal finance. This isn’t meant to scare anyone away from playing. It’s meant to show that the winners who kept their fortunes did a few simple things differently.

Every story below is built only on widely-reported, verifiable facts — no urban legends, no invented details.

1. Jack Whittaker — $315 million Powerball, 2002

Jack Whittaker of West Virginia won a $314.9 million Powerball jackpot on Christmas Day 2002 — at the time, the largest single-ticket US jackpot ever. He was already a wealthy construction company president, which is exactly why people assumed he’d handle it well.

He didn’t. Thieves stole $545,000 in cash from his car while he was at a Charleston strip club; a year later, another $200,000 was stolen from his car. Caesars Atlantic City sued him over $1.5 million in bounced checks. His beloved granddaughter Brandi died of a drug overdose — a tragedy he blamed on the winnings — and he later told ABC News he wished he’d “torn up the ticket.” Whittaker died of natural causes in 2020, having given $14 million to charity through the Jack Whittaker Foundation but never recovering the life he’d had before the win.

The money lesson: Wealth before winning didn’t protect him, because the problem wasn’t the amount — it was the sudden, public exposure. A legal and privacy shield matters more than a spending plan.

2. David Lee Edwards — $27 million Powerball, 2001

David Lee Edwards of Ashland, Kentucky, won Powerball in August 2001 and took home a $27 million after-tax lump sum. Within three months he’d spent $3 million; within a year, $12 million — mansions, luxury cars, a plane.

The money fed a spiral: Edwards and his wife fell into addiction to crack cocaine, heroin, and prescription pills, contracted hepatitis from dirty needles, and were arrested repeatedly. By 2006 the entire fortune was gone and the couple were living in a squalid storage unit in Florida. Edwards died penniless in hospice care in 2013, aged 58.

The money lesson: Speed kills. The winners who survive treat the first year as a planning year, not a spending year — and get professional help for any addiction before the money arrives, because a fortune accelerates whatever it touches.

3. Evelyn Adams — $5.4 million, twice (New Jersey, 1985–86)

Evelyn Adams beat the odds twice, winning the New Jersey Lottery in October 1985 ($3.9 million) and again four months later ($1.4 million) — a combined $5.4 million, paid as mandatory annuities. She was the state’s first two-time winner.

Adams was a compulsive gambler, and the steady annuity payments became steady fuel: she lost large sums at Atlantic City casinos, burned more on failed business deals and gifts to family, and by 2001 was living in a trailer.

The money lesson: Even the annuity — the “safe” option — can’t save you from your own habits. Structure helps, but the real protection is changing the behavior first, before the money flows.

4. William “Bud” Post — $16.2 million (Pennsylvania, 1988)

William “Bud” Post was on disability when he pawned a ring for $40 to buy 40 Pennsylvania lottery tickets — and won $16.2 million in 1988. He took the annuity, worth about $498,000 a year.

Within weeks he’d blown $300,000 of the first payment on a plane, businesses for his siblings, and a $395,000 mansion. His brother hired a hitman in a failed attempt to kill Post and his wife for the inheritance; a former girlfriend successfully sued him for a share of the winnings; Post fired a gun at a debt collector and was convicted of assault. He declared bankruptcy and died in Pittsburgh in 2006, about $1 million in debt.

The money lesson: Claiming without a lawyer and a plan invites every predator in your orbit. The first expense of a win should be the team — attorney, accountant, advisor — not the celebration.

5. Abraham Shakespeare — $30 million Florida Lotto, 2006

Abraham Shakespeare won a $30 million Florida Lotto jackpot in 2006, taking roughly $17 million in cash. Three years later he was befriended by Dorice “Dee Dee” Moore, who systematically drained his accounts and property. Shakespeare was shot twice in April 2009; his body was found in January 2010 buried under a concrete slab in a Plant City backyard. Moore was convicted of first-degree murder in 2012 and sentenced to life without parole.

The money lesson: The darkest risk of sudden wealth isn’t overspending — it’s becoming a target. Where your state allows anonymity, use it. Where it doesn’t, keep your circle tiny and let professionals handle the money.

The pattern: how winners actually lose it

Five very different lives, but the same four traps show up in every one:

• No team. None of these winners had a lawyer, a CPA, and an independent financial advisor in place before claiming. They managed life-changing money with the habits of a paycheck.
• Public exposure. Winners who can’t stay private attract relatives, “friends,” and outright criminals. Learn your state’s anonymity rules before your name goes public.
• Spending at full speed. Mansions, cars, and gifts in the first months lock in costs that keep burning long after the cash is gone.
• No tax plan. A jackpot is taxable income. The 24% federal withholding is only a down payment on the real bill, and state taxes can take another large slice. Winners who spend “the whole thing” discover this the painful way.

What winners who kept their money did instead

Here’s the encouraging part: keeping a fortune is mostly about a calm first 90 days, not genius investing. Planners who work with sudden-wealth clients give the same friendly advice every time:

• Don’t rush to claim. Most states give you months to collect a jackpot. Use that time to assemble your team — before you spend a cent.
• Sign the ticket, photograph it, lock it up. Then tell almost no one.
• Decide lump sum vs. annuity with real numbers. Run both options through our annuity vs. lump sum calculator before you choose — the 30-payment annuity is boring, and that’s exactly the point.
• Budget the after-tax reality. See what a jackpot is genuinely worth in your state with the lottery tax calculator — then plan from that number, not the headline.

Frequently asked questions

Do most lottery winners go broke?

You’ve probably heard “70% of lottery winners go broke.” That figure is widely repeated but doesn’t trace back to a rigorous study, so take it with a grain of salt. What is documented is that a meaningful share of big winners end up bankrupt or broke within a few years — and the five cases above are real. Winning isn’t a curse; sudden wealth without a plan is the hazard.

Is the lump sum or the annuity better for winners?

There’s no universal answer, but the annuity’s 30 graduated payments are a built-in guardrail against exactly the spending spirals in these stories. Our annuity vs. lump sum calculator lets you compare both side by side.

How long do winners have to claim a jackpot?

It depends on the state — generally 90 days to a full year from the draw date. Whatever your deadline, use the waiting period wisely: team first, spending later.

Holding a ticket for tonight’s draw? Check it against the official numbers — and sign it before anything else.