New York's Biggest Lottery Jackpots: The 10 Most Life-Changing Wins in State History

Written by Jackpot Staff

August 15, 2025

Introduction

Have you ever wondered what it would feel like to win hundreds of millions of dollars overnight? For a select few New Yorkers, this dream became an astonishing reality. Since its establishment in 1967, the New York Lottery has created more multimillionaires than any other state lottery system, transforming ordinary residents into some of America's wealthiest individuals with the simple purchase of a ticket. From retired school principals to maintenance workers, these record-breaking jackpots have not only rewritten personal fortunes but have contributed over $78.7 billion to New York's public education system.

In this comprehensive look at the biggest lottery wins in New York history, we'll explore the jaw-dropping jackpots, the fascinating stories behind the winners, and what happened after their lives changed forever. Whether you're a regular player dreaming of your own windfall or simply curious about these remarkable stories of instant wealth, these record-breaking New York lottery wins will captivate your imagination.

The Top 5 Largest Lottery Jackpots in New York History

1. Johnnie Taylor's $476 Million Mega Millions Win (2023)

The current record holder for New York's largest lottery prize is Johnnie Taylor, a 71-year-old resident of Howard Beach, Queens. On April 14, 2023, Taylor's life transformed when he matched all six numbers in the Mega Millions drawing, securing an astounding $476 million jackpot.

"I checked those numbers over a dozen times," Taylor recalled after his win. "I simply couldn't believe what I was seeing."

Like most major winners, Taylor opted for the lump-sum payment, receiving approximately $291.7 million after federal, state, and local taxes. His win represents not just a personal milestone but a historic moment in New York lottery history, eclipsing all previous records.

2. Goodtimez LLC's $432 Million Mega Millions Prize (2021)

Just two years before Taylor's record-breaking win, an anonymous entity operating under the name "Goodtimez LLC" claimed the second-largest prize in New York lottery history. The $432 million Mega Millions jackpot from September 21, 2021, was won with a ticket purchased at a Manhattan pizzeria.

The winner's decision to claim the prize through a limited liability company highlights a growing trend among major jackpot winners seeking to protect their privacy. While New York typically requires public disclosure for prizes over $5,000, legal entities provide a layer of anonymity that many winners now prioritize.

3. Harold Diamond's $326 Million Mega Millions Jackpot (2014)

Sometimes, the worst weather brings the best luck. For Harold Diamond, an 80-year-old retired elementary school principal from Wurtsboro, a rainstorm led to a life-changing decision. On November 4, 2014, Diamond and his wife Carol stopped at a Valero gas station in Middletown to wait out bad weather. During their impromptu stop, Diamond purchased a $10 Quick Pick ticket that would win him $326 million.

"My wife and I were driving to Middletown for dinner after voting," Diamond explained. "The weather was miserable. My wife insisted we stop to eat first, but I wanted to keep driving. I reluctantly agreed to stop. I bought a couple of lottery tickets while she went to the bathroom."

That reluctant stop resulted in Diamond receiving a lump sum of $197.4 million, netting $130.6 million after taxes. The former educator pledged to "help family and give back to the local community" with his newfound wealth.

4. Robert Bailey's $343.8 Million Powerball Win (2018)

Persistence paid off for Robert Bailey, a 67-year-old retired federal employee from Manhattan who won $343.8 million on October 27, 2018. What makes Bailey's story particularly remarkable is his unwavering commitment to the same set of numbers for 25 years - numbers he inherited from a family member.

"A family member gave me the numbers over 25 years ago," Bailey shared. "I faithfully played them in every lottery draw since then."

Like Diamond, Bailey's purchase was weather-influenced. He bought his winning ticket at a Harlem deli during a rainstorm. After discovering his win, Bailey admitted, "I didn't sleep the rest of the night." He chose the lump-sum payment of $198 million before taxes.

5. The Albany Seven's $319 Million Mega Millions Win (2011)

Sometimes, the biggest lottery stories involve not just what was won, but what was lost. In March 2011, seven IT professionals from the New York State Homes and Community Renewal agency in Albany pooled their resources for a $319 million Mega Millions jackpot. Their office pool, however, excluded an eighth colleague who declined to participate that week - a decision that cost him approximately $40 million.

The group, who became known as "The Albany Seven," each received about $19.1 million after taxes. Their win highlights the bittersweet nature of office lottery pools and the "what if" scenarios that often accompany major jackpots.

Notable Mentions and Remarkable Stories

Daniel Bruckner's Lucky Friday the 13th ($208 Million, 2011)

Challenging superstition, Daniel Bruckner, a 35-year-old at the time, won $208 million in the Mega Millions drawing on Friday, January 13, 2011. His win proves that sometimes, traditional "unlucky" days can deliver extraordinary fortune.

The Melville Store Employees ($202 Million Powerball, 2011)

Twenty employees from a Melville store formed "1937 Flatbush Ave Dodgers LLC" to claim a $202 million Powerball prize in 2011. Their collective win demonstrates how lottery pools can transform entire workplaces at once.

Lou Eisenberg: New York's First Lottery Legend ($5 Million, 1981)

While modest by today's standards, Lou Eisenberg's $5 million win in 1981 was groundbreaking - it represented the first major jackpot in New York Lottery history and was, at the time, the largest lottery prize globally.

Eisenberg's priority after winning was securing treatment for his wife Bernice's cancer, showing how even the earliest lottery winners often focused on family health and security before luxury.

Life After the Jackpot: What Happens to Winners?

Financial Decisions and Tax Implications

New York lottery winners face one of the nation's most aggressive tax structures. For major jackpots, the government takes a substantial cut:

• Federal withholding: 24% immediately, with additional taxes potentially due at filing time
• New York State tax: Up to 10.9% based on income brackets
• New York City residents: Additional 3.876% local tax
• Yonkers residents: Additional 1.477% local tax

For perspective, Johnnie Taylor's $476 million win likely resulted in approximately:

• $114 million in federal taxes
• $51.9 million in state taxes
• $18.4 million in NYC taxes
• Net payout: Approximately $291.7 million

Most winners, like Taylor, Bailey, and Diamond, opt for lump-sum payments rather than annuities, preferring immediate access to funds despite the reduced total. This decision often reflects practical considerations about investment control and life expectancy.

Privacy Challenges and Security Concerns

While some winners embrace publicity, others go to great lengths to maintain privacy. The "Goodtimez LLC" approach represents a growing trend of winners using legal entities to shield their identities. This strategy requires sophisticated estate planning but offers protection from the unwanted attention that often follows major jackpot announcements.

The Unclaimed Millions: Forgotten Fortunes

Perhaps the most surprising aspect of New York's lottery history is the staggering amount of prize money that goes unclaimed. As of March 2023, approximately 5 million tickets worth $78 million remained unclaimed in New York, including several prizes exceeding $1 million.

The largest unclaimed jackpot in state history was a $63 million Mega Millions ticket from 2002 - a fortune that eventually expired and was redistributed according to lottery regulations. Currently, a $1 million Cash4Life ticket purchased in Bay Shore, Long Island, in May 2023 will expire on May 28, 2024, if not claimed.

Common reasons for unclaimed prizes include:

• Lost or damaged tickets
• Lack of awareness about winning
• Misunderstanding of expiration policies (1 year for draw games in New York)
• Winners delaying verification due to disbelief

When prizes go unclaimed, the funds follow specific allocation rules: New York directs up to $60 million annually toward future prizes or promotions, with surplus amounts transferred to the state treasury.

Beyond Individual Winners: The Educational Impact

While jackpot winners capture headlines, the New York Lottery's most significant impact may be its consistent funding of public education. Operating under a constitutional mandate established by voter approval in 1966, all lottery revenue supports New York's schools.

In the 2020-2021 fiscal year alone:

• Total lottery sales: $8.59 billion
• Prizes to players: $4+ billion (46.5% of revenue)
• Aid to education: $3.59 billion (41.8%)
• Retailer commissions: $536 million (6.2%)
• Administrative costs: $344 million (4%)

Monroe County schools received $181 million that year, while statewide distributions followed a needs-based formula accounting for district size and income levels. Since its inception, the lottery has contributed approximately 5% of New York's total education funding.

The Evolution of New York's Lottery

The New York Lottery launched in 1967 with the slogan "Your Chance of a Lifetime to Help Education," beginning a journey that would see it become North America's largest lottery market. Early games like "Local Lotto" in the 1980s featured regional branding before multistate games dominated the landscape.

The introduction of Mega Millions in 2002 (replacing "Millennium Millions") and Powerball in 2010 dramatically increased jackpot sizes, setting the stage for the record-breaking wins we've explored. Despite brief scandals in 1975-1976 and 1986 involving rigged mail-in tickets and unsold "winning" tickets, the lottery has maintained public trust through transparency and regulatory oversight.

How to Play New York Lottery Games

Today's lottery players have more convenient options than ever before. While traditional retail locations remain popular, digital platforms have revolutionized access to lottery games. Players can now browse their favorite lottery games, review recent winners, and securely order state and national lottery tickets from home.

Is it legal to order lottery tickets online in New York? Yes! Players can order lottery tickets online in regulated states by using a secure, state-licensed lottery app like Jackpot.com. Licensed lottery ticket courier services, in collaboration with local retailers, ensure that your online lottery ticket orders are secure and compliant with state regulations.

Lessons from New York's Biggest Winners

New York's lottery history represents a fascinating intersection of chance, human behavior, and public finance. From Johnnie Taylor's record-setting $476 million windfall to the unclaimed $63 million prize that no one ever collected, these stories underscore both the life-altering potential and complex responsibilities that accompany major jackpot wins.

The winners profiled here share common experiences - initial disbelief, careful financial planning, and philanthropic intentions - that offer valuable insights for anyone dreaming of their own lottery success. Meanwhile, the lottery's enduring legacy of $78.7 billion in educational contributions demonstrates how individual fortune can systematically benefit public institutions.

As jackpots continue breaking records, New York's status as a lottery powerhouse seems assured, promising more transformative wins and educational funding for decades to come. Who knows? The next record-breaking New York lottery winner could be just one ticket away.

Ready to try your luck? With platforms like Jackpot.com, you can conveniently order tickets for New York's biggest lottery games from your phone or computer. Whether you're dreaming of joining the ranks of New York's lottery legends or simply enjoying the thrill of possibility, the next historic jackpot might be waiting for you!