Powerball · United States · 27 October 2018
Bailey ducked into the West Harlem Deli on Fifth Avenue to get out of the rain and bought a Powerball ticket there, playing the same six numbers a family member had given him more than 25 years earlier.
Advertised prize
$343,800,000
Cash value $198,086,518
Ticket
Own numbers
Outcome
Stayed private
Took the money, kept their life, said little since.
Robert Bailey, a 67-year-old retired federal government employee from Harlem, stepped into the West Harlem Deli on Fifth Avenue to get out of the rain and bought a Powerball ticket. The October 27, 2018 drawing came up 8, 12, 13, 19, 27 with Powerball 4 - the same line a family member had given him more than 25 years earlier and that he had played faithfully ever since. 'A family member gave me the numbers over twenty-five years ago and I faithfully play them,' he said. 'I said to myself, these look like my numbers. I tried to remain calm.' His half of the $687.8 million jackpot was advertised at $343.8 million, the largest prize in New York Lottery history; the other half went to Lerynne West of Redfield, Iowa. Bailey took the single cash payment of $198,086,518 and, after required withholdings, received a net check of $125,396,690. He waited more than two weeks before coming forward, claiming the prize in mid-November 2018. He said he planned to buy land and a house for his mother, set up investments for the next generation of his family, and travel to Las Vegas and the Caribbean. Asked if he would keep playing, he said: 'Yes, I will continue playing my numbers until this train runs out!'
His prize was the largest jackpot in New York Lottery history at the time he claimed it in November 2018, and he said then that he would keep playing the same numbers. As of 2026 no further public update on Bailey has been documented by a reputable source.
One detail worth keeping
He only stopped at the West Harlem Deli to shelter from the rain, then bought a ticket with numbers a relative had given him 25 years earlier.
Cheng 'Charlie' Saephan
Ended in tragedyPowerball · United States · 2024
$1,326,000,000
Laiza Chao joked to the Saephans before the draw that they were already "billionaires"; her $100 stake in a 20-ticket batch made it true.
Theodorus Struyck
Stayed privatePowerball · United States · 2023
$1,765,000,000
He bought the second-largest winning ticket in Powerball history about 500 yards from his own front door, at a cabin he had paid $90,000 for in 2010.
Edwin Castro
Went wellPowerball · United States · 2022
$2,040,000,000
The draw ran a day late: Minnesota's sales-verification system held up all 48 lotteries, so the $2.04bn numbers were drawn at 8:57 a.m. ET on 8 November 2022.
Manuel Franco
Stayed privatePowerball · United States · 2019
$768,400,000
He told reporters he had under $1,000 in his bank account when he spent $10 on the quick picks that won $768.4 million.
Cheng 'Charlie' Saephan
Ended in tragedyPowerball · United States · 2024
$1,326,000,000
Laiza Chao joked to the Saephans before the draw that they were already "billionaires"; her $100 stake in a 20-ticket batch made it true.
Two anonymous winners: a Singleton (NSW) couple and a Hawthorne (Brisbane) woman
Stayed privatePowerball (Australia) · Australia · 2024
A$200,000,000
The Brisbane winner found out at 6am, scanning her ticket on The Lott app while getting ready for the gym: every number lit up and A$100 million appeared on her phone.
Theodorus Struyck
Stayed privatePowerball · United States · 2023
$1,765,000,000
He bought the second-largest winning ticket in Powerball history about 500 yards from his own front door, at a cabin he had paid $90,000 for in 2010.
Saltines Holdings, LLC (Miami, Florida)
Stayed privateMega Millions · United States · 2023
$1,602,000,000
The biggest Mega Millions winner in history is a company: Saltines Holdings, LLC of Miami. The Publix that sold the $2 Quick Pick collected a $100,000 retailer bonus.
Every figure and quotation above comes from these.
Last verified: 2026-09-13