The Socialite Gangster Who Charmed the New York Literati

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Legendary New York City gangster Joey Gallo’s closest friends in the show biz world were actor Jerry  Orbach and his wife Marta. They when they happened to be eating in the same restaurant (Queen on Court Street in Brooklyn).

Jerry at that time was best known for playing gangsters in Broadway musicals—he’d played Mack the Knife in The Threepenny Opera and Sky Masterson in Guys and Dolls—but would later be famous for playing Detective Lennie Briscoe on several Law & Order TV series, and as the voice of Lumiere, the candelabra in Disney’s animated Beauty and the Beast.

Jerry first sought out Joey because he was playing a part in a movie based on Joey, and considered Joey research. Joey and the Orbachs both happened to be eating at Queen, a restaurant on Court Street in downtown Brooklyn. Jerry came over and introduced himself. They quickly became real friends, Jerry and his socialite and literati wife Marta.

Joey’s longtime best friend Peter “Pete the Greek” Diapoulos thought that Marta Orbach might be the biggest user of all time. She wanted to co-write Joey’s autobiography. First, that struck Greek as a bad idea, because everything in Joey’s life that would be worth reading about was also a forbidden topic. Plus, Greek didn’t like the idea that Mrs. Orbach saw Joey as a money-making opportunity.

Joey, on the other hand, liked the book idea a lot. Joey figured he needed to tell his own story on account of newspaper columnist Jimmy Breslin had written a “novel” about us called The Gang That Couldn’t Shoot Straight, which was turned into film starring Orbach, Robert De Niro, Jack Kehoe, Paul Benedict, Lionel Stander, and—making his feature film debut—Herve Villechaize.

The book and the film pissed off everybody on President Street because it made us look like clowns. The real story needed to be told so when Marta expressed an interest, Joey jumped at it. Marta wrote a book proposal and reportedly got an offer from Viking Press, but by that time Joey’s days were numbered.

Joey’s first wife, the former feathered Vegas show girl Jeffie Lee Boyd was best known for her exceptional tits and ass. She lived in Bohemian Central—that is, Greenwich Village—on Eighth Street, a tenement building with a garden in the backyard.

Joey and Jeffie met in a beatnik pad and he started hanging out there, the first indication to the President Street boys that this bohemian shit had an appeal to Joey, that he didn’t just think about juke boxes and scores. Jeffie had lots of contacts in the jazz world.

Her first husband had been the sax legend Gerry Mulligan. Joey could rap about poetry and life’s great mysteries. Joey wanted to be in show business. Not to perform, but to get his cut, just like he got a cut of so many bars and restaurants. He dug jazz and wanted to manage bass player Charles Mingus.

Joey could mix with that crowd in a way other hoods couldn’t even comprehend. He’d sit on the floor of a Lower East Side flat, one with the tub in the kitchen, and talk beatnik shit, how he’d seen the great balls of his generation blown out by hot lead.

When Joey went to parties, and he went to many parties, everyone remembered him—not big, but tough, and so, so cool. Joey Gallo was the only mobster in New York who showed up on the society pages.

He was a trendsetter. His fashion sense was both daring and impeccable. Plus, he was an intellectual, a guy who could sip a cocktail and discuss the commonalities between film noir and German expressionism. His new penthouse apartment had a section set aside for his easel. He’d taken up painting, colorful images of raw emotion, and the normally snobby art-world aristocracy was smitten. He wrote jazzy poetry and the kids with Van Dyke beards snapped their fingers instead of clapping their hands in appreciation. The beats came to call on him, smoke dope, and discuss how the cold war was a hoax.

He could talk politics with anyone. He said fascism propped up the paternal hierarchy and thus the repression of the masses. He said he understood communism’s appeal but didn’t think it was practical in a world of ambition—and ambition was something Joey knew about.

He could talk philosophy, how the ability to distinguish right from wrong was automatically blurred by modern society, that now there was no such thing as right and wrong, just smart and stupid, so you did what you could get away with.

He clearly had dreams of being king of the underworld, and yet his cover was as a bohemian—very charming. And he pulled it off.

New York elite uptown and downtown embraced Joey Gallo, who had spent so much time away and had so much creativity in his soul. Student and professors of the so-called “New Journalism,” a freewheeling stream-of-consciousness form of reportage, wrote about Joey like he was Sal Paradise speeding on the sacred urban road.

Here was a guy, a violent maniac, who went to prison for a decade, learned the speed-reading technique of Evelyn Wood, and read, and read, and read.

Here was a guy, a violent maniac, who went to prison for a decade, learned the speed-reading technique of Evelyn Wood, and read, and read, and read, and in essence gave himself a graduate’s degree level of knowledge in just about anything that fell under the liberal arts umbrella.

Joey always dressed the part. He was slow to adjust to 1970s clothes styles anyway, but to go out he wore what he’d always worn at night, as far back as the 1950s: dark shirt, white tie, pinstripe suit. He couldn’t have looked more like a gangster and that made those artsy types real happy.

During the last weeks of his life he was scheduled to appear on TV to discuss the new ways the boys from the press were telling stories. The show was to be called How They Cover Me, and he was scheduled to appear alongside Gore Vidal, Abbie Hoffman, Otto Preminger, and Bella Abzug. Joey was on the A list. As it turned out, the show had to go on without him.

He became friends with David Steinberg, a stand-up comic who would go on to have his own TV show. One of Steinberg’s funniest characters was a shrink who was nuts himself, who’d shout “booga booga!” at his patients—and you’ve got to wonder if maybe he didn’t, at least a little bit, consider Joey research.

Joey wasn’t just making show-biz friends, he was befriending people you’ve heard of, like actors Ben Gazzara, Peter Falk, and Joan Hackett. Writers, too—perhaps most noteworthy among Joey’s bookish pals was playwright Neil Simon, who wrote The Odd Couple.

Joey once told a hovering circle of literati that he plowed through ten books at a time in prison because a prospective writer—himself—had to read like a predator.

Joey was aware of the effect he had on people, he scared ’em, and how ironic it was that he wanted to write like Gregory Corso, to be the Walt Whitman of the streets, maybe write a book of verse called Cracked Bricks. He loved walking into Sardi’s, the Time Square restaurant known for its celebrity clientele, because he transcended. Even the celebrities stopped and stared when he came in, with the beautiful Sina on his arm.

Joey and Sina were married at his friend Jerry Orbach’s place, with Steinberg standing up as best man. The President Street Boys weren’t invited. Joey was getting married for the second time since he got out, second time in under a year. Whatever.

Joey and Sina’s wedding service was performed by a Presbyterian reverend, on account of the bride and groom having been divorced, making them ineligible to get married in a Catholic Church. He was forty-two. She was twenty-nine. The clown minister kept getting Sina’s name wrong—wanted to call her Tina—and Joey didn’t think it was funny. Luckily, he was sane enough to know that whacking a guy during his own wedding was bad form.

Joey wore a double-breasted suit and a polka-dot tie. The bride wore a simple white dress. The music was provided by singer Allan Jones. He was best known for his appearances in a couple of Marx Brothers pictures, A Night at the Opera in 1935 and A Day at the Races in 1937. At the wedding he warbled The Lord’s Prayer.

Joey had a new life, a new wife, a new step kid, Lisa, who was in show business herself and really going somewhere. Joey treated his new step-daughter like his own, and he didn’t want to think about incoming bullets.

The new family and new life was a large reason he wasn’t hanging out in Brooklyn as much as he had back in the 1950s and early ’60s. They were Manhattan people now, mingling with the movers and shakers.

Joey had plenty of scratch to throw around. He owned nightclubs, sweatshops, skimmed this and that, ran the rackets here and there, controlled coin-operated machines just about everywhere. At play Joey talked about Jung and Freud, at work he plotted to wipe out the Colombo motherfuckers one hood at a time with bullets through their brains.

On April 13, 1972, the Daily News announced in a front-page headline that the NYPD knew who had killed Joey Gallo at Umberti’s Clam House. You didn’t have to get very far into the story however to tell that this wasn’t true. The story even varied depending on whether you were reading the first or second paragraph. The first said that investigators had narrowed the suspect list to three individuals, although they refused to comment on whether or not the killer was local. The second paragraph said that they believed they knew who did it, but being able to prove it was another thing and their investigation was ongoing. Police Commissioner Murphy said that they had witnesses to the shooting that were not connected with organized crime and that these witnesses’ statements were being given most credence.

The most interesting part of the day’s Joey Gallo news was buried in the story: Jerry Orbach and his “writer wife” Marta were being kept under round-the-clock guard. The reason, according to the paper, was that the Orbachs were friends of Joey’s, had befriended him after his release from prison just about exactly a year earlier, and Marta had been collaborating with Gallo on his autobiography. This didn’t quite explain why the Orbachs needed protection.

Orbach didn’t see the reason for the fuss either, saying, “I firmly believe there is no danger, but someone thinks that because we were associated with Joey we are now in danger. It’s ridiculous. Marta’s book is about our relationship with him. It’s not the Valachi papers or anything of an inside look at the mob.”

As for “playing Joey” in a movie, Orbach didn’t think there was much of a comparison. He told Time magazine: “(Jimmy) Breslin’s book portrayed Joey as a clown. Then when I met Joey, I was absolutely amazed to find out that maybe he had been a wild kind of nut before he went to prison, but something had happened to him inside.

Marta Orbach said that before the tragedy she had talked to Joey about security and he said that there was no way to tell when and where someone might try to hit him. He figured he was safe from the button guys because he was a button guy himself but he did fear wannabes, some nobody with a gun who wanted to make a name for himself.

Joey said some things Marta didn’t quite get. He said that as long as he struggled he figured he was safe, but if he started to do well for himself, raking it in like the old days, then he might be vulnerable to a hit.

Marta said, “Joey once asked me who I preferred, Sartre or Camus. I almost fell into my plate of spaghetti. A few days later Joey showed up at our house in the middle of the night and announced that he and I were going to write a book together.” Joey, she said, practically moved in with them for a month to work on the book.

While he was there his hosts introduced him to all of their best friends, who in turn introduced him to all of their friends until in no time Joey knew everybody who mattered in the world of New York publishing and show business. Joey and Marta ended up working on two projects, a memoir for Viking Press and a comedy screenplay for a movie about prison life.

Marta’s dog was stolen during this time period. Marta wondered if it might be because of Joey.

“Joey, do you know anyone who steals dogs?” Marta asked.

“What kind of dog do you want?” Joey asked.

Police explained that the guard for the Orbachs was placed on duty after someone called in a report that a car was being tampered with by two men. The car belonged to the Orbachs, and was parked across the street from their West 22nd Street apartment. Bomb squads reported to the scene and the car was towed to the police lab.

No bomb, but the Orbachs went under guard.

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Adapted from MAFIA HIT MAN: CARMINE DIBIASE by Frank Dimatteo and Michael Benson. Reprinted with permission from Kensington Books. Copyright 2021.

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