For a brief, surreal moment, James “Shannon” Farthing was the luckiest man in Kentucky. Just days ago, the 50-year-old walked into the Kentucky Lottery office hand-in-hand with his 77-year-old mother, grinning ear to ear as they claimed a jaw-dropping $167.3 million Powerball jackpot.
But within 72 hours, Farthing was sitting in a Florida jail cell—bloodied, bruised, and back in the only place he’s known longer than freedom: prison. His rapid fall from lottery fairytale to felon has now stunned the nation, revealing a violent and deeply disturbing criminal history that spans three decades.
Man wins $167 MILLION Powerball jackpot. 3 days later, he’s arrested for assaulting a guest and kicking a deputy. This story is unreal. pic.twitter.com/vCRupMWguX— Law&Crime Network (@LawCrimeNetwork) July 4, 2025
On April 26, Farthing’s life changed when he bought a $2 Powerball ticket from a Speedway in Georgetown. Against all odds, he matched every number, becoming the largest single Powerball winner in Kentucky history.
Two days later, on April 28, he and his mother Linda Grizzle went public with their win. They posed for photos holding a giant check and spoke emotionally to local outlets about plans to “give Mom a proper Mother’s Day” and “do things right this time.” People Magazine reported that Farthing seemed overwhelmed with gratitude, saying, “God’s been good to us.”
But by April 30, that dream imploded.
Authorities say Farthing, now flush with millions, had flown with his girlfriend to Florida and checked into the TradeWinds Island Grand Resort in St. Pete Beach. That night, he allegedly punched another hotel guest in the face during a heated argument. When a sheriff’s deputy tried to break it up, Farthing turned violent again—kicking the officer directly in the face, according to Unilad.
BREAKING: Powerball winner James Farthing arrested at Florida resort just 72 hours after claiming $167M prize. Allegedly kicked deputy during drunken brawl. pic.twitter.com/wA7EixRZKn— NBC Miami (@NBCMiami) July 4, 2025
Farthing was arrested on four charges: felony battery on a law enforcement officer, battery, resisting arrest, and a parole violation. He was booked into the Pinellas County Jail. His bail: $11,000, which he reportedly paid using his newly acquired winnings. But the real story was only beginning.
Records uncovered by New York Post show Farthing has spent over 30 of his 50 years behind bars. His rap sheet includes convictions for drug trafficking, assault, domestic violence, organized crime, bribery, and smuggling drugs into prison—a crime he committed with the help of his own mother.
In total, Farthing has been transferred between 25 correctional facilities in Kentucky alone. One former corrections officer described him to The Sun as a “textbook manipulator who never saw prison as punishment—just home.”
Perhaps most shocking: at the time of his jackpot win, Farthing was on parole for a laundry list of offenses. He was forbidden from traveling out of state, especially without informing his parole officer. Yet after collecting the check, he disappeared to Florida—with no permission, no notice, and no intention of obeying the law.
James Farthing: 50 years old. 30 years in prison. On parole. And now a millionaire. He violated parole within 48 hours of winning. pic.twitter.com/LYDeJdZ8eU— Crime Watch USA (@CrimeWatchUSA) July 4, 2025
Farthing’s latest arrest could now derail his lottery windfall entirely. Kentucky’s parole board confirmed they are reviewing his violation and may revoke his release, sending him back to prison indefinitely. Meanwhile, Florida authorities are weighing felony charges that carry up to five years in prison, according to AP.
The woman arrested alongside Farthing has been identified as Jacqueline Fightmaster, his on-again, off-again girlfriend. She was reportedly “screaming, intoxicated, and making no sense,” according to WKYT. Police sources said she attempted to pull Farthing away from the arresting officer during the scuffle.
Public reaction has been swift—and brutal.
This guy wins $167M and ends up in jail two days later. The universe handed him everything. And he threw it away. pic.twitter.com/UyGv8JRXzY— Jaye Marie Green (@JayeGreenUSA) July 5, 2025
Some are calling him a “walking cautionary tale.” Others are asking whether someone with such a deeply rooted criminal history should ever have been eligible to claim such winnings.
But lottery officials insist the system is blind. “We don’t background-check winners,” one spokesperson told Business Insider. “If your ticket is valid and you’re of age, you get the prize.”
Farthing chose the lump-sum option, meaning he already collected over $77 million in cash. That money is now sitting in an account he shares with his elderly mother. According to ABC News, there’s no legal mechanism to freeze or reclaim the funds unless fraud can be proven—something authorities say is unlikely at this stage.
As for his mother, Linda Grizzle has not made any public statements since her son’s arrest. But people close to the family told CNN she is “completely heartbroken and embarrassed,” and is now “considering moving out of Kentucky entirely.”
Farthing is scheduled for arraignment on July 15 in Pinellas County Court. If found guilty, he could be returned to Kentucky to serve the remainder of his parole violation sentence—and face additional time in Florida for his new crimes.
What began as the ultimate American dream story—a man getting a second chance after years of hardship—has spiraled into a national spectacle. In less than a week, Farthing went from poverty to riches… and straight back into a jail cell.
For the public watching, it’s no longer a story about luck. It’s a brutal reminder that money can buy freedom—but it can’t change who someone really is.
