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$167.3M Powerball winner, 50, exposed as a career criminal who spent 30 years in jail before striking it rich: report

July 3, 2025
in News
$167.3M Powerball winner, 50, exposed as a career criminal who spent 30 years in jail before striking it rich: report
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He’s flush with cash — and mug shots.

The winner of Kentucky’s largest lottery jackpot who was arrested in Florida days after claiming his riches has a 16-page rap sheet and decades-long criminal history – earning him a jaw-dropping collection of booking photos along the way.

James Shannon Farthing has spent 30 of his 50 years alive behind bars at 25 different correctional institutions before he, along with his mother and girlfriend, claimed the $167.3 million Powerball jackpot in April, The Smoking Gun reported.

The career criminal turned overnight millionaire has racked up convictions across nine counties in Kentucky for a litany of offenses including strangling a girlfriend, bribing officers while in prison and selling cocaine to an undercover cop, according to the report.

Three lottery winners holding a $167.3 million Powerball check.
James Farthing, his mother Linda Grizzle and his girlfriend Jacqueline Fightmaster accepted his Kentucky Lottery win together in April. Kentucky lottery

The lowlife’s string of consistent crime started when he was just a teenager, with arrests for anything ranging from theft to reckless driving. He was only able to complete 10 years of formal schooling and earned his GED in prison.

In his later years, Farthing upped the ante as he started dealing in drugs, even roping his mother in on a scheme to smuggle marijuana into a maximum security facility. Farthing accepted a plea deal that absolved Grizzle and he was sentenced to 10 years, the report said.

Even in the slammer, Farthing couldn’t keep out of trouble. He was frequently placed in “administrative segregation” after doing things like smuggling a variety of drug and alcohol paraphernalia into the prison and charging inmates to return items he stole from them like a bully on a school playground.

Man and woman holding lottery ticket.
Farthing and his mother committed a marijuana smuggling plot together. WKYT

The tatted-up criminal was frequently denied parole in part because of his seemingly infinite offenses with few signs of stopping.

In the rare cases he was granted parole, he’d lose it just as quickly for violating terms of his release, usually through testing positive for drugs like marijuana.

Farthing’s appearance has been well documented in his countless mug shots — showing the transition from his baby-faced clean-shaven days to more recent times sporting a gray goatee and packing on a few extra pounds.

And his newfound wealth hasn’t stopped his antics.

Mugshot of James Farthing.
Farthing’s rap sheet is 16-pages long. PCSO

Three days after cashing in with his 77-year-old mother Linda Grizzle and girlfriend Jacqueline Fightmaster, he was arrested in the Sunshine State after allegedly slugging another guest in the face and kicking a deputy who tried to intervene.

Farthing also violated his parole when he left Kentucky without notifying his parole officer. He was required to because of his lengthy criminal record.

Man with tattoos and sunglasses in a store.
Farthing has been in and out of prison ever since he was a teenager. WKYT

Farthing was just freed from a Kentucky jail last week, according to the Kentucky Parole Board, but now has to face the charges from the Florida fight.

A sliver of his lottery winnings was put towards his $11,000 bail. He pleaded not guilty and is scheduled for a July 14 arraignment, where he could face up to five years in prison for the remaining battery count on the deputy attack alone.

The post $167.3M Powerball winner, 50, exposed as a career criminal who spent 30 years in jail before striking it rich: report appeared first on New York Post.

Tags: Arrestdumbest criminalsFloridaKentuckyLottery
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