‘Gamblers,’ Episode 2: The Last Great American Pool Hustler

Gamblers is a podcast about men and women who live by their wits and wagers. People who bet big on themselves, and won. From a road-hustling pool shark to a punk-rock horse handicapper to a sports bettor who could move lines, the six-part anthology series focuses on the fascinating lives of professional underground gamblers and how they make their money.

Every town in America, even the one you live in right now, has a top pool player—someone who is the king of the local pool hall, that nobody else can beat. But back in the day, every town also had a steer man. A steer man is someone who puts the word out to road gamblers about the local pool hall kings and how good they are, what their strengths and weaknesses are, what kind of stakes they liked to play for, the full scouting report. A steer man would reach out to a road gambler and offer to put them together with these local champs in exchange for a cut of the profits. And after Scott Frost, the Go Off Kid from Des Moines, had huge scores in Chicago and St. Louis, he started getting calls from steer men around the country. One of them tells him about a big score down in Ocala, Florida.

“There was this poolroom called Big Daddy’s,” Scott says. “And in Big Daddy’s, there was this guy named Tony Bologna—my whole goal was to get down with Tony Bologna. Now we knew that this process was going to take some time. It wasn’t like, this guy wasn’t stupid, right? He actually owned a bunch of Italian restaurants there in town, and he was a connected guy. He was probably pushing 70 years old, but he gambled like a mad man. And if you could get him down and beat him, you could win a lot of money.”

Scott and his steer man hang around Big Daddy’s for four or five days and get Tony Bologna used to seeing them. And Scott doesn’t bullshit Tony, either. He’s straight with him about how good he is. Because he figured if he could make a game with Tony and beat him and he was honest about how good he played, he’d have a lot better chance of being paid than if he tricked Tony into thinking he was worse than he really was.

The problem with that approach was it meant that when he finally did get a chance to negotiate a game with Tony, he’d have to give up a lot of weight.

“I was giving Tony Bologna nine to six,” Scott recalls. “That means I had to make nine [balls]. Tony had to make six, but I was also giving him something called ‘the scratches don’t count.’ That means that Tony could push the cue ball anywhere he wanted at any time.”

“The problem with that was that I didn’t know how to defend against giving a guy whose scratches don’t count. I’ve never played this game before.”

Scott was completely snakebit. He dropped the first six games. And he didn’t think there was any way he could win with this handicap. He had only about $7,000 on him, so he was nearly bust. He went over to his partner to tell him he wanted to quit, and they agreed to take their last $1,000 and head back north.

“And as I turn around to go shake Tony Bologna’s hand, I [see that] he had already broken the balls and he scratched,” Scott remembers.

Scott had given Tony the scratches, meaning he could miss the object ball whenever he wanted. But when Tony put the cue ball in the pocket, it had to come back out and be put on the table somewhere, which was a huge advantage for Scott. He looked back at his partner and told him: “We have to play.”

“Mind you, we have one barrel left,” Scott says. “If I lose this game, we got $200 to get back to Detroit from freaking Florida. Well, true and amazing story. We played for 76 straight hours from that moment.”

Let me do the math for you. That’s three whole days. No stopping. No sleeping.

“And when that 76 straight hours was up, I was up $86,000,” Scott says. “It got so bad, we were playing like $8,000 a game. It got so bad that this guy was shooting at my pocket all the time. Like he was delirious. Looking back, it’s lucky that the guy lived. His legs were black and blue.”

Scott knew this wasn’t going to end well. Word got to Tony’s sons and they showed up to stop the match. They ended up rushing Tony Bologna to the hospital.

“I’m sure he was dehydrated,” Scott says. “He was in the hospital for a week.”

Scott’s legend grew even further from there. One score after the next, he was starting to build quite the bankroll.

“I had two cars: I had a Suburban and a new Cadillac—and a boat,” says Scott. “I had probably a hundred and some thousand dollars in assets that were paid off in cash. So for a kid, that’s not bad.”

They stopped calling him the Go Off Kid from Des Moines. Now, Scott Frost was the Freezer.

“And then when I was probably 22 to 23, I got a call from the best money player in the world at the time,” Scott says. “His name was James Walden out of Oklahoma City. He said, ‘Freezer, I think we’d be a great team.’”

James Walden had a reputation as being the best money nine-ball player in the country, which means Scott was probably now seen as the top money one-pocket player. If they partnered up and combined their bankrolls, they could take on anyone. Scott didn’t hesitate to jump in the car and drive to Oklahoma.

James and Scott hit the road together, and their first stop was Houston, Texas, which had long been the gravitational center of the pool universe, with maybe more poolrooms per capita than any other city in America. Which is why it was so incredibly unlucky that the first poolroom they walk into they run smack-dab into the last guy they wanted to see.

“We go into this one poolroom and there’s nobody in there but one guy,” Scott remembers. “And this one guy—his name is Jimmy King—he’s an ex-con and an ex-felon. He knows everybody in the pool world, and he spots us and comes over to us, and he tells us, ‘Here’s the deal, boys. I know you’re here in town to make money, but you ain’t getting past me. If you want to make money, I’m getting 25 percent. Now I’ll steer you around, but I’m getting 25 percent.’”

He was the only guy in Houston who knew how good they were, and unless they cut him in on their profits, he was going to make sure they couldn’t make a game with anyone.

“Jimmy King was also noted for robbing a pro pool player named Jimmy Wedge,” Scott says. “He had duct taped him to a chair in a hotel room after he had steered him around for about three months.”

They asked Jimmy King to let them sleep on it, and that night they weighed the pros and cons. On the one hand, Houston was the mecca of pool. There was a lot of money to be made there, money they couldn’t make anywhere else in the country. On the other hand, Jimmy King might steer them around until they won a decent amount of money ... and then try to kill them.

The next day they told Jimmy they were in.

To hear the full Scott Frost episode, click here, and be sure to follow on Spotify and check back every Wednesday for new ‘Gamblers’ episodes. This excerpt has been lightly edited for clarity and length.