James Shannon Farthing, 50, of Georgetown, Kentucky, who recently claimed part of a $167.3 million Powerball jackpot, is facing renewed legal trouble just days after the win, as reported by The Daily Mail.

Farthing, who split the prize with his mother, Linda Grizzle, was arrested two days later in Florida and is now under scrutiny for a lengthy criminal history spanning more than 30 years.

Kentucky Powerball winner, James Shannon Farthing, jailed in Florida after altercation with police. ‍♂️ pic.twitter.com/isfsyNb6MP

— ThOm GilmOre® (@ThOmGilmOre) May 3, 2025

Farthing has accumulated an extensive rap sheet, including charges ranging from domestic violence by strangulation and drug distribution to attempted bribery of correctional officers, according to reports.

His criminal record began in his teens and continued into adulthood, with Farthing spending a total of approximately 30 years behind bars. He reportedly earned a GED while incarcerated after completing just 10 years of formal education.

In later years, Farthing’s offenses escalated to drug trafficking, including a plot to smuggle marijuana into a maximum-security prison.

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According to The Smoking Gun, Farthing took a plea deal that cleared his mother of any criminal responsibility in the smuggling case, resulting in a 10-year sentence for him alone.

While in prison, Farthing was repeatedly disciplined for rule violations. Officials say he was placed in administrative segregation several times for smuggling contraband, including drugs and alcohol-related items.

He was also accused of extorting fellow inmates, demanding payment for the return of their stolen belongings.

Farthing was denied parole multiple times due to his continuing misconduct and what officials described as a persistent pattern of criminal behavior.

Over the years, his physical appearance has been documented in a series of mug shots, displaying a transformation marked by extensive tattoos.

The winner of that recent $167.3 million Powerball jackpot is a “persistent felony offender” who has been locked up in at least 25 different Kentucky correctional institutions https://t.co/vCmqIQqqS2 James Farthing, 50, has spent nearly 30 years behind bars pic.twitter.com/zozxUJrk8Q

— The Smoking Gun (@tsgnews) July 2, 2025

Despite his release and lottery win, Farthing’s troubles continued. On April 30, while vacationing at the TradeWinds Island Resort in St. Pete Beach, Florida, Farthing was arrested after allegedly punching another guest and assaulting a responding law enforcement officer.

Deputies responding to a call at the resort’s bar around 11:10 p.m. reported that Farthing was intoxicated and combative. Authorities say he kicked a deputy in the face, causing swelling and redness under the officer’s eye.

Farthing is now facing charges in Florida that include felony battery on a law enforcement officer, as well as misdemeanor counts of resisting an officer without violence and battery.

Authorities in Kentucky have also issued a warrant against him for violating parole related to previous theft and drug convictions.

Farthing and his mother purchased the winning $2 ticket at a Clark’s Pump-N-Shop in Georgetown, Kentucky. They opted for a lump sum payment of $77.3 million rather than receiving the jackpot in 30 annual installments.

At the time of the win, Grizzle told reporters that the money would “change their lives” and help pay off debts.

Farthing’s arrest and the public release of his criminal history have sparked widespread attention and questions about how he will manage his newfound wealth moving forward.

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