Controversial Powerball Winner Farthing Reverses Cold Streak With Victory In Court

The bad boy of the lottery world, James Farthing, got some good news in a Lexington, Kentucky courtroom Monday. The charges in the latest of his three arrests since splitting a $167.5 million Powerball jackpot with his mother in April 2025 were dismissed following testimony on Farthing’s behalf by his ex-girlfriend, Jacqueline Fightmaster.

Farthing was arrested in March for second-degree burglary and marijuana possession, accused by Fightmaster of breaking into her home and stealing $10,000 in cash. Police said they found him a couple of hours later, in his car, with marijuana in the vehicle.

But at a preliminary hearing, Fightmaster essentially said it was all a big misunderstanding. According to her testimony, she and Farthing had a spat, he went to her house, and when she got home she couldn’t find her cash. She suspected Farthing of stealing it and called the police.

She later realized it was “in a Gucci shoebox,” she testified, but wasn’t able to get the charges against Farthing dismissed until it went to a preliminary hearing.

One down, two to go

Farthing, 51, is not yet in the clear for one of his other arrests.

On Feb. 11, he was charged in Scott County with intimidating a participant in the legal process. A woman called the police and told them Farthing was among a group that pulled a gun on her.

He is also facing a drug charge related to that arrest and is scheduled to appear in court for arraignment on May 28.

In a much higher-profile incident, Farthing was arrested in Florida last April, two days after he claimed his Powerball prize, for getting into physical altercations while traveling with then-girlfriend Fightmaster. A seemingly heavily intoxicated Farthing got into a fight with a fellow guest at TradeWinds Resort, kicked a Pinellas County sheriff’s deputy in the face, and tried (unsuccessfully) to flee — as captured in bodycam footage.

He initially pled not guilty but later waived his hearings and served a brief sentence. Fightmaster was charged with a misdemeanor count of disorderly conduct in the incident.

None of these arrests would have made any headlines if not for Farthing suddenly becoming a relevant public figure by winning the April 26, 2025, Powerball drawing along with his mom, Linda Grizzle. They claimed the prize on April 28 — accompanied by Fightmaster for the publicity photos with the oversized check.