Ray William Johnson: True Story Podcast - This Rich Guy is in BIG Trouble // The James Farthing Lottery Story

Episode Date: May 26, 2026

The story of James Farthing centers on a dramatic turn of fortune where a historic lottery win was immediately followed by a cascade of serious legal troubles. In April 2025, Farthing, a Kentucky resident with a prior criminal record, made history by winning a massive $167.3 million Powerball jackpot, the largest ever in the state. However, just days after claiming the prize and publicly promising to turn his life around, he was arrested at a hotel bar in Florida for battery on a law enforcement officer. Over the following year, Farthing's legal spiral worsened with multiple additional arrests in Kentucky, including charges for a 100-mph hit-and-run crash, witness intimidation, and a burglary charge involving his ex-girlfriend.

So this guy is about to win $167 million. And then he's going to jail. So the guy's name is James, and James is about 50 when this story starts, and he's living in Georgetown, Kentucky. And James has a problem. In fact, he has a lot of problems. The dude can't seem to stay out of jail. And he's been in and out of lockup basically his whole life for all kinds of reasons. Drug trafficking, burglary, theft, weapons charges.

he got locked up for choking a girlfriend of his, and even while locked up, he can't stay out of trouble. He gets additional time for fighting other inmates, smuggling contraband, bribing a prison guard. This dude has been locked up in 25 different correctional institutions, primarily across nine counties in Kentucky, which has got to be some kind of world record.

But all that might be about to change, because one day in 2025, he happens to be out of jail at this point, on parole, and he goes to a local gas station with his mom. And they pool their money together, and he buys a handful of $2 lottery tickets, which he often buys lottery tickets while he's there. The next day, his mom goes online and she checks the winning number,

and sure enough, kaboom. One of the tickets is a winner, and they won the jackpot. And it just happens to be the biggest Powerball prize in Kentucky history, $167.3 million. Damn. Shortly after that, the Kentucky Lottery has James and his mom come down to the headquarters for a big press conference, and they hold up that massive oversized check. Here is a picture of James with his mom and his girlfriend holding up the check.

And so, instead of taking the money in 30 years worth of payments, James and his mom choose to take the one-time lump sum cash payment of $77.3 million. So now the dude is rich. So no need to do any more drug trafficking or burglary or whatever he was doing. After he collects his winnings, he and his girlfriend drive from Kentucky all the way down to St. Pete Beach, Florida, because I guess they're going to celebrate by staying at this beachfront resort. Now his girlfriend is this woman, Fightmaster. And I'm not making that up. Her actual name is Jackie Fightmaster. So anyway, James and Fightmaster are at the hotel bar, and they're,

drinking and celebrating and bragging about all the millions they just won. And James, he starts getting belligerent and picking arguments with other hotel guests. And he gets into an argument with one guy at the bar, and this argument gets really heated. And suddenly, pow, James punches the guy in the face. And a bunch of people immediately jump in, trying to break it up. Then Fightmaster's drunk ass tries to get involved, and she's yelling and screaming and actively trying to fight other bystanders and pretty quickly the police show up and they try to break it up and one officer grabs the guy who James punched and he pins him down on the ground then James goes to kick the guy

and he misses and boom he accidentally kicks the cop in the face and if you slow the body cam footage way down you can see the guy James is trying to kick is here and you can see James's leg come in and miss the guy's head and kick the cop right in the face anyway Then you can see James try to run and he gets tased and a cop tackles him. And then, bam, James gets arrested. Here's his mugshot. Also, Bam, Fightmaster gets arrested. Here's her mugshot.

Nine days later, James has bailed out. And he ends up pleading guilty to battery and resisting arrest and he pays a fine and he moves on. And Fightmaster is only in jail for like a day because she did not kick a cop in the face. Anyway, a few months later, James is back in Kentucky, and he's cruising down the road one night in his black Porsche, and I assume this is a Porsche he bought with his $77.3 million in lottery money. Anyway, he's cruising down the road, driving like an asshole, and he keeps going faster and faster and faster until he reaches over a hundred miles an hour. And suddenly, skirt, kaboon, he slams into another car from behind. And instead of getting out and checking on the other driver, he runs away. And police, they don't catch him that night.

But eventually they do, and bam, they arrest him. And he's criminally charged with leaving the scene of an accident. Now from here, James could lay low and let all this blow over and, you know, enjoy his millions of dollars. But that's not what he's going to do. Instead, he decides to meet up with this woman in Lexington. And he picks her up and he takes her up and he takes her. back to his place. Now, I don't know if this woman is just a friend or if he's cheating on Fightmaster or what, but at some point during the night, he offers her some kind of gummy.

Apparently, it's the marijuana kind. And this woman, she isn't entirely sure what's in this gummy. Like, what, is James trying to roofie her or something? So she doesn't really want to take it. But James, he's kind of pressuring her. So she takes it. And whatever is in this gummy, it her up, and she starts freaking out and she becomes convinced that other people living in the house have guns and that they're trying to kill her. So she hides under a desk and she calls 911. Pretty quickly, police show up and they come into the house and they find the woman still hiding under the desk, still scared out of her mind. They also find some drugs and a handgun. And so, bam, James gets arrested again and charged with intimidation.

And later he gets out on bail again, because, you know, he has millions of dollars to bail himself out. But his problems keep going. About a month later, he and Fightmaster are hanging out at a racetrack slash casino in Lexington called Red Mile Gaming. And for whatever reason, these two get into an argument. And this argument, it's pretty big. And James, he gets super pissed off. And he leaves, and he drives all the way back to Fightmaster's house, where he had been staying lately because he's there to get his things and leave.

And I don't know why this multimillionaire doesn't have his own place at this point, but, you know, I don't know, whatever, he's staying with her. So he gets there and he goes up to her side door and this triggers her home security cameras. So now, Fightmaster can see him on her phone. And I guess she's still pissed off at him over the fight that they just had. So she calls the police on him. And so police get there. And by the time they're there, he's already gotten his stuff and left.

But then Fightmaster gets home. And she had $12,000 stashed in a shoebox in her house. And she discovers that it's missing. And she tells police that it was James who took it. And I don't know why someone who just won $77.3 million would need to steal $12,000. But that's what she tells police that he stole it. So once again, police are looking for James. Meanwhile, he goes back to Red Mile Gaming for some reason, and a few hours later, police spot his black Porsche there in the parking lot, and James, he's chilling there, getting high on a little Zaza.

And so, bam, they arrest him once again, this time for burglary, here's his mugshot. And again, he gets out on bail, and then he has a preliminary hearing, and Fightmaster is there at this hearing. and she's actually no longer accusing him of stealing her $12,000. She gets on the stand and she testifies and she says that she actually misplaced the shoebox that it was in, but she has since found that shoebox and that this was all just a big misunderstanding. Sure, Jan. And so anyway, the burglary charges against James are ultimately dropped. And so he's not in jail at the moment, but, you know, give it a week or two.

I'm sure he'll be right back. Thank you.