Robert Bailey

Powerball Winner • NY • 2018

Jackpot (2024$)

$428,000,000

lump sum

Age at Win

67

Retired postal worker

Summary

Robert Bailey, a 67-year-old retired USPS worker from Harlem, won half of $687.8M in October 2018—largest in NY history. He played the same numbers for 25 years. In 2021, he won AGAIN ($1M second prize). No scandals or troubles in 7 years.

Quick Facts

Win Date
October 27, 2018
State
NY
Winner Type
individual
Marital Status
single
Ticket Type
Own Numbers
Payment Choice
lump sum
After Tax
$125M

Timeline

W
Oct 27, 2018win

Won $343.8M Powerball jackpot

C
Nov 14, 2018claim

Claimed prize at Resorts World Casino

*
Jan 23, 2021other

Won $1 MILLION second prize in Powerball (matched 05, 08, 17, 27, 28)

C
Jun 17, 2021claim

Claimed $1M prize; received $612,247 after taxes

Notable Quotes

"I had to see a lawyer and a financial adviser"

**Present:** Robert Bailey (alone), Yolanda Vega (NY Lottery rep), Gweneth Dean (Lottery Director)

"With any type of money, and this type of money also—you have to watch out for your safety."

-

"Make good investments"

"Give back to Manhattan—that's where I'm from"

"When I saw the eight and the 12 I was in shock—woah—I looked and I kept going across. And I didn"

"I still want to be me; I can"

"You have to watch out for your safety, that"

"I want to do the right thing and take care of it for the next generation of my family. That"

"Yes, I will continue playing my numbers until this train runs out! I"

Analysis

Protective Factors

  • +41 years federal employment discipline
  • +18-day claim delay for planning
  • +Hired lawyer and financial adviser before claiming
  • +Single - no spouse complications
  • +Previous $30K lottery win experience

How They Found Out

Bailey played same numbers for 25+ YEARS - given by a family member. Original: 8-12-13-19-27-40, changed 40 to 4 for Powerball. "It was raining that day so I went into the deli to get out of the rain and bought my ticket there." Checked numbers at 11:30 PM watching college football: "When I saw the eight and the 12 I was in shock—woah."

Research Quality: verified Last Updated: 12/24/2024Years Tracked: 7