Freddy "the Beard" Bentivegna at Chris's Billiards in Portage Park
Freddy "the Beard" Bentivegna at Chris's Billiards in Portage Park Credit: Nick Murway

There are many improbable stories about the pool hustler Freddy “the Beard” Bentivegna. Like the time he married a Playboy bunny. Or the time a crew of pool-loving FBI agents recruited him to infiltrate Chicago’s “head houses” to find Bernadine Dohrn. Or the time he took up meditation and his sister found him levitating in the bathtub. But maybe the best place to start is where Freddy himself usually starts, with the story about the time he hustled Archie Karas out of a million dollars. He’s told it so many times he’s got all the timing and details down cold. It goes like this:

About 20 years ago, a group of hustlers decided to lure Karas to a small town in Pennsylvania to play pool against an eccentric, high-rolling degenerate billionaire, played by Freddy the Beard. Karas was no sucker. He was one of the biggest gamblers of all time. The Horseshoe Casino in Vegas made a special $25,000 chip that only he could use. “This guy broke champion poker players,” Freddy says, “executed them.” But Freddy was a pro at pool—and at being a lemon man, or looking like an easy mark.

“I had the whole town gaffed up,” Freddy says, “the bartender, the waiter. I was Audie Weiss.” At the time, Freddy had a bad leg. He looked like he could barely stand.

They met at a bowling alley. Karas proposed a game of eight ball, $40,000 a game.

“I don’t have $40,000,” Freddy says. “There’s no way he can win anyway, but still . . . you know, if he had somehow miraculously won, we had exits.”

Freddy won the first game, eight $5,000 chips. Karas won the second. “I’ve got to pay him the eight chips back. I’m all shaky, you know, I mean my nerves are a little . . . anyway, I went ahead, and we switched the game to one pocket. I beat him out of $100,000 that night, right? He pays me off in four $25,000 chips. But the best part of the evening was, now we’ve got to go pay the time [for the table]. So the counter guy says, ‘That’ll be $21, sir.’ Now I really want to dig it in and make sure this guy believes this. So I don’t pay the time. I’m patting myself down for $21, you know, to really make it look like I’m a cheap guy. And he goes, ‘Awww, that’s OK, that’s OK, Audie, I’ve got it.’ He reaches, he takes out the $21, he pays the time! I beat him out of $100,000, and he pays the time!”

A few weeks later, Karas went back to Pennsylvania and lost again. “He wouldn’t quit! ‘No, no, no,’ he says, ‘I can beat this guy. His leg is gonna give out any minute.'”

By the time Karas caught on, Freddy had already cashed $200,000 in chips. Karas still owed him $800,000. The hustlers who arranged the games were tentative about collecting. Karas got suspicious. Back in Vegas, he started asking around about a guy with glasses and a bad leg who played one pocket. His associates identified the eccentric billionaire as Freddy the Beard. Freddy never collected his $800,000.

A few years later, Internet message boards made it possible to identify any stranger who wandered into a pool room. And just like that, the art of hustling, and Freddy the Beard’s entire way of life for the past 35 years, was over.

Freddy the Beard is 73. He still has a beard, which he darkens with Grecian Formula. His eyes look sad. He has never had any sort of job besides pool hustling. Over the past few years, he has become sort of an elder statesman of pool. He was inducted into the Bank Pool Hall of Fame in 2006 and does the emcee duties at the annual Hall of Fame dinner and at the Derby City Pool Tournament in Louisville. Several times he’s delivered the eulogy at funerals. He did such a good job that one person has requested his services in advance. (“The guy’s younger than I am!”)

Ten years ago, his friend Randy Givens, who’d had some success with The Eight Ball Bible, convinced him to write his own how-to guide, not to hustling, but to his true specialty, bank pool, where you have to bounce a ball off a rail before it goes in the pocket. “So great was Fred’s devotion to bank pool,” his friend, the late Billiards Digest columnist George Fels, wrote of the Beard’s early years, “that he could scarcely make any other kind of shot.”

Freddy never intended to be a hustler. He grew up in Bridgeport. His father was a jazz drummer who had fought in both world wars and, according to family legend, toured with Buffalo Bill’s Wild West Show as a very young teenager. He was frequently on the road. Freddy’s mother was 20 years younger than his father and a stereotypically doting Italian mama. As a kid, Freddy was small and skinny and loved drawing and comic books. This did not make him popular or powerful in the neighborhood. He discovered pool by accident one day while he and his friends were waiting for a lane at the bowling alley. He never bowled again.

“Now pool, you don’t need to be a bruiser, you know? And in my neighborhood, if you were good at anything, you got respect. It didn’t matter. I mean, there was a famous kid—he was famous because he could pee across the street. So the fact that I was now the best pool player in the neighborhood, pretty quick I was big.”

But soon Freddy got bored being the best 14-year-old pool player in Bridgeport. He started seeking out action elsewhere, mostly at Bensinger’s, which was, for nearly a century, the most important pool institution in Chicago. When Freddy started going there, it was still in the Loop, at 29 W. Randolph; later it moved to a rat-infested basement at Clark and Diversey in Lakeview, where it finally died in the late 70s.

Freddy in Bensinger’sCredit: Courtesy Freddy Bentivegna

When Freddy first started going to Bensinger’s, he was underage. He had to sneak in. He’d play with anyone who asked him, but he discovered that no one there played for free. They were all hustlers. And he was a sucker. But he had to play them to learn. Inevitably, they would take all his money and he would walk home to Bridgeport. (“That was your tuition,” observes Freddy’s friend Ed Young. Young himself is a legendary figure in the pool world; he and his business partner David Kersenbrock make custom cues that sell for upwards of $25,000.)

Freddy’s first successful hustle did not take place at Bensinger’s. It occurred back on his home turf, at 26th and Wallace, where he lured two Bensinger’s regulars, Mexican Johnny and Gus the Greek. The table was in terrible shape, all taped up, with ashtrays under the pockets to catch the balls. But Freddy knew how to play it. Mexican Johnny gave up and went home. Gus continued to play until Freddy broke him. Then Freddy had an epiphany:

“Now he wanted me to give him a quarter or something for carfare. I’m thinking of all the long, cold walks. I said, ‘Screw you, pal.’ It’s what you had to do to survive. I could go home, I’ve got a mother to go home to, I can get something to eat in the icebox. I break this guy, he’s gonna have to sleep in the street, he ain’t got nothing to eat—I’m worried about him! And he’d break me! If you wanna survive in the world, you’ve gotta toughen up.”

“The real hucksters are motivated from the start. I want to kill you. I want to eat your eyeballs, OK? That’s how you think.”—Freddy “the Beard” Bentivegna

Freddy graduated high school early and got what he calls a “mob scholarship” to the University of Illinois; he lasted a few weeks before returning to Chicago and Wilson Junior College (now Kennedy-King). He dropped out after a year and a half and joined the army. They sent him to Germany. When he got out he made a few attempts to get square jobs, but it didn’t take. Instead he played pool. He hung out at Bensinger’s and in south-side pool rooms so he could work on his bank game with legends like Bugs Rucker. The gangbangers protected him. He married and divorced the Playboy bunny. He traveled around the country hustling. Hustlers were like gunfighters with cues, wandering into strange towns, looking for action. He’d sleep in bus stations. He learned how to sneak out of hotels without paying the bill. (Bring a rope and lower your luggage out the window, then walk out the front door.) He would stay up for days on end, shooting pool until he was completely busted.

“We were hard-core,” he says. “That’s why I figure any old-time players would kill today’s guys. Deep down, we’ve got more stuff. We weren’t relaxed. We were killers! Now everybody’s friendly. If I’m gambling with you for big money, I’m not going to be friendly, OK? I want you to fear me. And fear what I’m going to do to you. Because my goal is to go all the way. You know, that doesn’t change. If I start off, ‘Well, I want to win a few games,’ once I win a few games, what happens? You let up. I’ve achieved my goal. It’s hard to get remotivated again. The real hucksters are motivated from the start. I want to kill you. I want to eat your eyeballs, OK? That’s how you think. It’s not my nature, it’s not me. I’m a softie. But if you want to survive among other people like that, that’s what you have to learn.”

Back when he was hustling, Freddy points out, there were no credit cards or ATMs. You had money or you didn’t.

“Today, everybody’s got a little something,” he says. “That’s the problem. That’s why people can’t identify with all the things that we did. Because they weren’t under those kinds of pressures. You know. Being on the road, busted, hungry. OK? It’s cold outside. Your feet are wet, OK? No place to sleep. What are you gonna do? Are you gonna take the moral high ground? You might, that night. The next night . . .”

But sometimes conditions would be too desperate to do the right thing. There’s a practice called dumping, when a player has a backer who puts up the money for him and then loses on purpose and splits the money with his opponent. A lot of hustlers made their living that way.

“It’s a terrible, terrible practice,” Freddy says. “I did it a couple times. Only a few times, which is . . . it’s actually kind of commendable that I only did it a couple times, OK? Honest to God, believe me when I tell you. I don’t like it. It don’t make me feel good. Even the money when you get it, it’s like tainted money, you know? You make up reasons to do it. ‘The guy’s no good, he’s a creep, he deserves it.’ Just not good.

“Like I say, it was a tough life.”

Every year Freddy went down to Johnston City, Illinois, in Little Egypt for the annual Hustler’s Jamboree, so he could meet Minnesota Fats and guys with names like Low Down Dirty Stinking Red. There was a lot of gambling in Johnston City, because when the tournament began in 1961, the official prize was just $2,000 for three weeks of pool, and everyone still had to pay for travel, food, and lodging. Freddy watched. Gene Skinner, the Fullerton Kid, an all-around great pool player, finally noticed him and took him under his wing. Freddy’s pool game improved more in a week than it had in 15 years. In 1970, when he was 30, he came in fifth in the one-pocket division of the World’s All Around Pocket Billiard Championship Tournament, much to the astonishment of the pool world.

Freddy moved to Hollywood. He loved it. He got a backer, a producer of pornos named Mike Weldon. (He sat in on a shoot once, but was asked to leave because he started laughing. “Don’t you understand,” Weldon told him, “these girls think they’re serious actors, OK?”) He played pool with Jimmy Caan. He wore purple polyester pants and Indian print shirts. Sometimes he was known as Freddy the Hippie. He moved back to Chicago only at the behest of Artie Bodendorfer, a hustler who’d just bought Bensinger’s and who paid for his ticket back (three times, because Freddy blew the first two checks) so he could stir up business.

As he moved into his 30s, Freddy grew philosophical. “I got to thinking. I said, ‘You know, people have been having kids for thousands and thousands of years. There must be something to it.’ You know? ‘Maybe I ain’t so smart like I thought I was.’ So I decided to get married and have kids. So I spotted my wife. I said, ‘I’ll take her.'”

Freddy and his then-wife Theresa in Johnston City (note the Captain America T-shirt)Credit: Courtesy Freddy Bentivegna

Her name was Theresa. She was living in a commune in Fort Lauderdale, where Freddy liked to spend the winters. She was the commune leader’s girlfriend. She was guarded at all times. She wasn’t averse to leaving with Freddy. But she had guilt issues. “She says, ‘No, I’m true, I’m loyal. The only way I’d ever go with you is if you kidnapped me.'”

Freddy enlisted his friend Sugar Shack Johnny. They marched into the commune one morning. Sugar Shack held the hippies at bay while Freddy and Theresa grabbed her things and left. “We weren’t gonna hurt ’em. They were like little fragile birds, you know?” A week later Theresa went back. A few days after that, she called Freddy and asked him to kidnap her again. This time he wasn’t taking any chances. They got on a plane for Chicago.

“When they got off the plane, it was snowing,” says Cat Adami. “She’d never seen snow since she was five. It’s super romantic, even though it didn’t work out. When I was in college, I was this innocent geek. I kept thinking, how will I ever top that?”

Adami is Freddy and Theresa’s daughter. She’s 42 now and a writer. If her life were a movie, she says, it would be called Pool Hustler’s Daughter, and it would begin like this:

In the summer of 1972, the Bentivegnas were living above Kiyo’s Japanese Restaurant on Clark Street, near the Century Theater and, probably not incidentally, Bensinger’s. The neighborhood could politely be described as “bohemian.” “One night,” Adami says, “some people at the theater got all drugged up and decided to rob the Japanese restaurant. I think they were watching a blaxploitation movie.”

The three gunmen held the patrons of the restaurant hostage for more than an hour. Cat, then seven months old, and her parents were trapped upstairs until the police evacuated them; they waited out the rest of the night in Bensinger’s. (“My dad wanted to go out and get his pool cue.”) There were 100 police officers on the scene, and helicopters. The gunmen demanded a getaway car for themselves and four of the hostages, which the cops provided. (The gunmen failed to notice it was marked.) A high-speed chase ensued throughout the city, ending in a shootout in Chatham, just off the Dan Ryan. Two of the gunmen were killed. The hostages were unharmed. The story made the front pages of both the Tribune and the Sun-Times.

“Life as a pool hustler’s daughter begins with a bang!” Adami announces like a movie-trailer voice-over artist. “It never stops being dangerous. It’s exciting. It’s over-the-top. The pool world is full of tall tales. Things are always stranger than fiction.”

Adami’s parents split up when she was nine. She lived in Lincoln Park with her mother and younger brother, Dino. Freddy was on the road a lot. When he was in town, he would take her to pool rooms on Sunday afternoons. The men all ignored her. She didn’t have much of a head for pool, and she didn’t want to learn. Instead, she spent the time reading and writing and listening to stories and improving her powers of observation. “The pool room was a microcosm of the world outside,” she says. “The people were socially inept, but they had talent.”

She went to school at Francis Parker, where she had a scholarship. She didn’t discover the social advantages of having a pool hustler for a father until college. As a teenager, her existence felt precarious. “I always felt like I was flip-flopping between two worlds,” she says. “Being a pool hustler’s daughter is a shaky situation. You have a Mercedes—for a day. Or you have thousands of dollars for vacation, and then at other times you’re worried about the bills. I had this feeling I was not able to be completely honest.” Three days before she was scheduled to leave for college at Tulane, where she had another scholarship, she still didn’t have a plane ticket or spending money for the semester. One of her aunts gave her a wad of cash that she kept under the mattress.

Freddy and his daughter, Cat Adami. Freddy’s cue was custom-made by Bobby Hunter.Credit: Nick Murway

As an adult, she took a job as an accounts manager for an IT consulting company and stayed there for 15 years. She married a software engineer. They live in Lincoln Park with their two children, blocks from where she grew up. She never gambles. Instead, she prefers to consult experts and then make informed decisions. If she were forced to fill out an NCAA bracket, she would copy Nate Silver’s.

Nonetheless, she grew to appreciate her father: his prodigious reading, his open mind, and the advice he gave her and her friends, even if it usually came filtered through his experiences in the pool room. “Once I bought a used car,” she says. “It didn’t reverse. My dad went in with two scary people to get my money back. I think they were mobsters. My punishment was that I was not allowed to cry.

“Freddy’s real gift is not playing pool. It’s being the world’s best narrator for stories. His timing’s right. The facts are right. There are so many stories.”—Ed Young, a legend in the pool world and maker of custom cues

“The most important thing my dad taught me,” she continues, “is that there’s magic in the world and thoughts are important. You have to make your own magic. You can’t rely on other people. My dad laughs a lot at The Secret, but that’s what he did his whole life. Like, if you want to go to Hot Springs for a vacation, you say that over and over. Even if there’s no money. Then someone will call and say, ‘Remember the $5,000 I borrowed from you two years ago?'”

Five years ago, she quit her job to write full-time. Freddy had already self-published his first book, Banking With the Beard, and a companion DVD. He set up a website. “Mostly he understands that writing pool books is not an endeavor to make anyone rich,” George Fels explained in Billiards Digest at the time. “There is simply no over-estimating the value of Banking With the Beard, though, for players serious enough about the game to elevate this lone aspect.”

Much to everyone’s surprise, Freddy’s pool instruction was on the square. “You automatically think a player would give bad advice,” says the cue maker Ed Young, “but mostly they’re not articulate enough to explain. I went to see him while he was writing. He reverse engineered everything. There were white dots all over the table and a protractor. The system he came up with is genius. For something like this to come from a pool hustler, I never would have thought it in a million years.”

Banking With the Beard and its 2010 successor, The GosPool According to the Beard, are heavy on technical information and diagrams, but like a good teacher, Freddy threw in a few stories from his hustling days to keep the students awake. This led to Adami’s great epiphany: instead of marketing Freddy’s pool tips, why not try to market Freddy?

“Freddy’s real gift is not playing pool,” says Young. “It’s being the world’s best narrator for stories. His timing’s right. The facts are right. There are so many stories.”

Adami’s inspiration was Minnesota Fats, famous not for being a pool hustler—or at least not just for being a pool hustler—but for being a personality, a fixture on late-night talk shows, subject of profiles by writers like George Plimpton. He would give demonstrations in football stadiums and miss every shot, Freddy says, but it wouldn’t matter, because he was Minnesota Fats and he had stories to tell.

The hook for Freddy, though, was going to be slightly different: Freddy was the last of the pool hustlers, the last living link to Fats, the gunfighters, and the glory days of Johnston City.

Freddy himself is a bit more modest. “I’m the only guy that’s alive, plus I can talk,” he says. “Many don’t, you know. I could never be a Fats. Believe me. And I’ve got a big ego.”

Nonetheless, he obliged his daughter by writing The “Encyclopedia” of Pool Hustlers, his first book for a mainstream audience: 300 pages of stories about characters he met during his hustling career in alphabetical order (by the first, not last, name), plus a glossary of useful hustling terms, such as “lemon,” “ham ‘n egger,” and “shit mickey.” He self-published the book last fall, and Adami drew up a marketing plan. The selling of Freddy the Beard would begin with local and national media coverage (both the billiards press and mainstream), a book release party in Manhattan, and an appearance on the Interview Show at the Hideout, all of which would—she hoped—lead to a large mainstream publisher picking up the “Encyclopedia,” appearances on late-night TV, a pool-hustling reality show on the model of Dancing With the Stars, and a full-blown pool revival across the country.

“Now he deserves his due,” she says. ‘He owes it to me. I’ll say, ‘I’ve got the New York Times on the phone. The sacrifices I made for you need to be legitimized in some way. Don’t eff it up.'”

The Color of Money was shot at Chris’s Billiards. Freddy taught Tom Cruise how to break the rack playing nine ball and then talked his way into being an extra.Credit: Nick Murway

These days, Freddy’s working more than he ever has in his life. Every Wednesday, Adami gives him five tasks for the week. He handles all the distribution for his books and videos himself from his house in Bridgeport. Fans call to order and are astounded to learn they’re actually speaking to Freddy the Beard.

He was nervous about having to play the role of “Freddy the Beard” for the first time in public, at the Interview Show last month. “I got nothing in common with anyone in the joint,” he told the host, Mark Bazer. “There’s one pool hustler in here, and I brought ‘im.” Within a few minutes, though, he was bantering with Bazer about pool-hustler slang and telling stories about Minnesota Fats. As Adami had predicted, he was a natural on the talk-show couch.

Still, after his trip to New York for the book party, which was held in a nightclub in Hell’s Kitchen, he was most excited about having learned from a friend the secret to preparing good corned beef.

In his spare time, he bakes bread, plays with his two dachshunds, watches TV (he’s especially fond of Doctor Who and Game of Thrones), and chauffeurs his grandchildren to and from school. He and Ed Young have formed what Young calls “pool player social security.”

“We raise money for their funerals,” Young explains. “I make a phone call, and in eight hours I was able to get 70 of the top pool players in Chicago [to donate money]. We told them, ‘It’s the one good thing you’ll do in your life . . . maybe.’ Freddy says it’s the biggest hustle in pool history.”

Freddy still goes to tournaments, and he still plays in pool rooms, $10 games. The number of pool tables in Chicago is less than 5 percent of what it was in 1970, but every poolroom regular still knows the Beard. He doesn’t hustle anymore. “I’m a nice guy,” he says. “I don’t do anything to these people except play. You know, just passing time. They don’t have any idea what I’m capable of, OK?”

The “Encyclopedia” doesn’t go too deep into the darker aspects of the hustler’s life. And it’s probably just as well. The best hustling stories are about putting something over on somebody, not about selling off parts of your soul in order to survive. The Archie Karas story is great because Karas is a hustler himself and Freddy outhustled him. It holds to a code of honor: never pick on the weak. And it has a sweet coda.

“Did Freddy tell you where the money went when he hustled Archie Karas?” Young asks. “The first thing he did was send [his son] Dino to culinary school. He paid all the tuition up front. Freddy will do the right thing, but he’s not always in the position to do the right thing. He’s done stuff I can’t even imagine. But I guarantee all the stories are true. It’s a miracle he’s around to tell these stories.”

Adami is sure Freddy will be around and telling stories for at least 20 more years, till he’s in his 90s. She attributes this to good longevity genes. Freddy attributes his survival to his Sicilian paranoia. But also—jail, drugs, dumping for money—they all interfere with the simple act of playing pool.

Did Freddy ever consider doing anything else?

He doesn’t hesitate for a second. “No.”

Watch the Reader‘s Ben Joravsky play a round of pool with Freddy.