Lottery Winner Horror Stories: You Win Sum, You Lose Sum

July 18, 2022

Can a multimillion-dollar jackpot really be a curse? How do you even begin to spend all that money? People often joke that it would be nice to have a “problem” like that. But the financial, marital, and legal disasters that have befallen many suddenly rich lotto winners are no laughing matter. Whether you are blessed with a small inheritance or a once-in-a-lifetime windfall, you should see a trusted financial and legal advisor as soon as possible after gaining it. Otherwise, you could end up like these winners whose lottery dreams turned into nightmares:

Curtis Sharp Jr.

Curtis Sharp Jr. worked as a dishwasher when he suddenly won the New York lottery in 1982. He became known as “the Five Million Dollar Man” after winning that amount. He was a charismatic character known for a larger-than-life personality and free-spending ways, and it did not take long for his lottery dream to crash. Parties, women, new houses, and flashy cars took a toll on his winnings and on him. The year after winning, he left his wife and threw a lavish wedding for himself and his new bride – who tossed him out after five years. Soon he was borrowing money from his first wife.

Sharp’s story ends happily; he stopped drinking and, when last heard from, he had become a minister.

“Wild” Willie Seeley

Like many groups of co-workers, Willie Seeley and his workmates bought a lottery ticket and vowed to share the winnings. Unlike many other groups, they won. The 16-person pool, who called themselves Oceans 16, held one of three winning tickets for the prize of $450 million in August 2013.

Split Oceans’ one-third take 16 ways, and you get only about $4 million, and $4 million is not what it used to be. It was a nice windfall but hardly the life-changing, never-work-again fortune that so many people dream of. Seeley and his wife also suffered from constant intrusive media attention and pleas for charity from distant relatives and even complete strangers.

It only took a few weeks for winner’s remorse to set in. “There are days I wish we were back to just getting paid every two weeks,” he told a newspaper.

Denise Rossi

This winner’s downfall was her own doing.

Denise Rossi went a little too far in heeding the advice that lottery winners often hear: Keep your winnings secret until you have a plan for the money and a safe place to keep it. But Rossi kept the news from her own husband.

She won $1.3 million in the California lottery in 1997 and almost immediately filed for divorce from her husband, Thomas. Two years later, Thomas discovered the hidden asset and took her to court. He was awarded every penny.

Janite Lee

This South Korean immigrant also created her own bad lottery luck, but it was due to an excess of kindness, not selfishness.

Lee was working in an Illinois wig shop in 1993 when she won the state lottery – $18 million. She moved her family into a million-dollar gated community in St. Louis and started spending her $620,000 a year in philanthropic ways, like political contributions that got her dinners with Bill Clinton and Al Gore and a donation to the Washington University School of Law, which gratefully put her name on a reading room. In less than 10 years, she had less than $700 to her name and $2.5 million in debts. Lee’s actions were admirable but ultimately as self-destructive as the other winners’ spendthrift ways.

For many winners, things go south when other people learn of their windfalls. Any significant earnings such as lottery winnings, casino payouts, personal injury settlements, and inheritances should be treated with caution and planned for appropriately.

There are MANY ways to preserve privacy and make wise investments. This starts with estate planning to ensure your family is taking care of for the rest of your life and theirs. This may also include creation of Trusts or business entities that will provide asset protection for your investments such as real estate, cash in the bank, life insurance policies and so on. The list is endless but requires a consultation with an estate planning attorney and trustworthy financial adviser.

You do not have to be an overnight millionaire to use the services of an estate planner, and you will not need luck to keep your assets healthy. Start by contacting OC Estate & Elder Law at (954) 251-0332 or for a free phone consultation. Our attorneys are fluent in English, Spanish, and Russian.