Biggest NY Lottery Winners – Historic Jackpot Stories

These New Yorkers didn’t just play – they made history. Mega Millions and Powerball produced a long, expanding list of lottery winners. Meet the biggest NY lottery winners who hit historic jackpots.

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1. Johnnie Taylor – Largest NY Mega Millions Winner ($476M, 2023)

A 71-year-old New Yorker who recently retired has now been given the chance to enjoy retirement to the fullest by becoming fortunate lottery winners! The Mega Millions jackpot won by Johnnie Taylor is the largest jackpot ever won in New York.

Johnnie won the New York record-breaking Mega Millions jackpot worth $476 million on April 14, 2023 and has chosen to take home the cash value of the prize, giving him more than $157 million after state and federal taxes are deducted.

2. Goodtimez LLC – NY Mega Millions Jackpot Winner ($432M, 2021)

Two players on behalf of Goodtimes, LLC claimed the big Mega Millions jackpot of $432 million in the draw on September 21, 2021. They were the only players to match all six numbers drawn – the white balls 36, 41, 45, 51 and 56, plus the gold Mega Ball 13.

3. Robert Bailey – NY Powerball Lottery Winner ($343.9M, 2018)

Apparently, not all massive jackpots in the Big Apple come from Mega Millions. Some of the state’s most iconic wins are New York Powerball lottery winners, including one of the largest ever, the $687.8 million jackpot. This win entitled Bailey to half of the advertised prize!

“A family member gave me the numbers over twenty-five years ago and I faithfully play them,” Bailey said. Apparently, winning large sums of money makes the winners’ names to be added to the New York lottery winners’ list yet another time!

Bailey’s winning ticket was worth $343.9 million and he chose to take a single lump sum payment. After withholdings, Bailey received a prize of $125,396,690. Will Bailey continue to participate in lottery games after his amazing win? “Yes, I will continue playing my numbers until this train runs out!”

4. Harold Diamond – NY Mega Millions Lottery Winner ($326M, 2014)

Harold Diamond, an 80-year-old retired school principal from Wurtsboro, was driving home with his wife when they encountered very bad weather. Harold’s wife became very nervous and made him pull over. Reluctantly, he stopped the car. While they waited out the storm, they grabbed some food and Harold purchased a 10-line $10 quick pick Mega Millions ticket for the draw on November 4, 2015. Unbelievably, Harold hit the jackpot!

“I was in a ditcher, a real daze” he said when he found out. There is no better feeling in the world than financial stability, especially at a crucial time in your life like retirement. For Harold and his family, this win allowed him to have just that. Harold took the lump sum cash prize of $130,676,438 and said that he planned on sharing his win with his family and his community.

5. Nancy Viola – Mega Millions Jackpot Winner from Staten Island ($169M, 2016)

Nancy Viola, a homemaker living in Staten Island, was caught up in the Powerball fever when that lottery game’s jackpot neared $1 billion in January 2016. She sent her husband to Foodmart on Victory Boulevard in Willowbrook to purchase Powerball tickets for the next draw, but this time, with his two extra dollars, he purchased a Mega Millions ticket instead.

After the Mega Millions draw on January 8, 2016, Nancy and her husband checked their ticket over and over in complete disbelief. They had hit the jackpot! “There are no words to describe it. I still can’t believe it. It’s surreal, but exciting and wonderful at the same time. I’ve thought about my plans and want to make some investments and just be secure for the future,” Nancy stated. They decided to take the lump sum cash prize of $64,796,160 and just like that, their lives changed forever.

6. Tammy Pratt – Upstate NY Mega Millions Winner ($126M, 2015)

Tammy Pratt had one rule: only buy lottery game tickets when stopping for gas. One day between meetings, the real estate agent from South Fallsburg stopped for gas and to purchase tickets at the South Fallsburg Food Mart for the February 27, 2015 Mega Millions draw. But this time, she bought $4 worth of tickets instead of her usual $1. “I just had a feeling I should get more than one,” Pratt said.

After the winning numbers were announced, Tammy heard that the sole winner of the jackpot was from her town. Jokingly, she told her husband they had the winning ticket, but when she compared the winning numbers to her ticket, she saw that the last line actually matched up. Tammy elected to take the lump sum cash prize of $54,000,000. Although already content in her life, Tammy said that she was also excited for “this added adventure.” She immediately put herself on a waitlist for a brand-new Tesla.

Amazingly, Tammy lives in Sullivan County, an upstate county of 76,000 residents which is also Harold Diamond’s home. It’s quite unusual for such a small community to have two winners of $100 million-plus Mega Millions jackpots in just three months!

How to Order NY Lottery Tickets Online & Get Your Chance at Huge Prizes

Want to win like these lucky New Yorkers? Now you can – by ordering your NY lottery tickets online with TheLotter NY. Whether you’re at home, at work, or on the go, you can easily choose your favorite draw, pick your numbers, and place your order in just a few clicks. Your ticket is safely stored in your personal account, and if you win, you’ll receive instant email notifications. It’s a simple, secure, and convenient way to play – and of course, New York’s anonymity rules apply to these wins, just like they did for the winners we mentioned.

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