Flush with cash and mired in controversy, one Kentucky lottery winner has made headlines not just for his $167.3 million Powerball jackpot, but for his astonishing criminal past.

James Shannon Farthing, 50, is no stranger to the law, boasting a staggering 16-page rap sheet. With 30 years spent behind bars across 25 different correctional institutions, his criminal history is nothing short of alarming.

Having been convicted in nine Kentucky counties for an array of offenses—from assault to drug dealing—Farthing’s transformation from a career criminal to an overnight millionaire raises serious questions. His track record includes strangling a girlfriend, bribing correctional officers, and dealing cocaine to an undercover cop.

James Farthing, his mother Linda Grizzle, and his girlfriend Jacqueline Fightmaster accepted his Kentucky Lottery win together in April. Kentucky lottery

From a young age, Farthing exhibited a pattern of delinquency, starting with theft and reckless driving as a teenager. His minimal education—only 10 years of formal schooling before earning his GED in prison—speaks volumes about his choices.

Inexplicably, he brought his mother into a drug smuggling plot, further demonstrating a blatant disregard for the law and the consequences of his actions. His plea deal, which spared his mother from jail time, resulted in Farthing receiving a ten-year sentence—nothing more than a slap on the wrist for his extensive career of crime.

Farthing and his mother committed a marijuana smuggling plot together. WKYT

Even during his time in prison, Farthing’s troublesome behavior never ceased. Regularly placed in “administrative segregation,” he continued to smuggle contraband and extort fellow inmates like a schoolyard bully.

His repeated parole violations underscore a troubling trend: every time he’s granted early release, it seems he can’t resist the urge to fall back into old habits, often testing positive for drugs shortly thereafter.

Farthing’s journey through the criminal justice system has left a permanent mark, with a plethora of mug shots capturing his evolution from a clean-shaven youth to a grizzled man with a gray goatee. His notorious lifestyle has only intensified following his lottery win.

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

Moreover, he violated his parole by leaving Kentucky without notifying his officer—a requirement given his extensive criminal history. With this latest arrest, Farthing finds himself in hot water once again.

Farthing has been in and out of prison ever since he was a teenager. WKYT

Recently freed from a Kentucky jail, Farthing now faces serious charges stemming from his altercation in Florida. A portion of his lottery winnings has been funneled into an $11,000 bail. He stands accused, and a scheduled arraignment looms where he could face substantial prison time for his latest battery charges.