On April 7, 1972, at 4:30 in the morning, Joey Gallo was celebrating his 43rd birthday at Umberto’s Clam House on Mulberry Street in Manhattan’s Little Italy. He was eating shrimp and scungilli with his wife, his 10-year-old stepdaughter, and his sister.
Four men walked through the door carrying revolvers and opened fire. Twenty shots rang out in the small restaurant. Gallo flipped a table to shield his family, but took bullets in his back, elbow, and buttock. He staggered outside and collapsed next to his black Cadillac on Hester Street. He bled out on the street on the same day he was born.
Joey Gallo was not just another mobster killed in a restaurant. He kept a pet lion named Cleo in his Brooklyn basement. He read Sartre and Camus in prison. He befriended black gangsters when other Italian mobsters would not sit next to one. He kidnapped his own bosses’ top men and declared war on an entire crime family.
He was 5’6", blond, blue-eyed, and had been diagnosed by a court psychiatrist as a paranoid schizophrenic. He was known as Crazy Joe, and for a brief, violent period, he was the most dangerous man in Brooklyn.
Gallo was born on April 7, 1929, in Red Hook, Brooklyn. His father, Umberto, was a bootlegger who moved into loan sharking and ran a small restaurant. He did nothing to discourage his three sons from entering the life. Joey was the middle child. His older brother Larry was quiet and calculating. His younger brother Albert, known as Kid Blast, was a loyal soldier.
Joey dropped out of high school at 16. After a car accident left him with a nervous tick, he leaned into the instability. He formed a small crew with childhood friend Pete Diapoulas, known as Pete the Greek, and a man named Frank Illiano. They started with jukebox and candy machine rackets.
The scheme was simple. They would approach a bar or restaurant and tell the owner he needed a jukebox. If the owner refused, Joey would hold a knife to his throat until he changed his mind. Within a few years, he controlled the jukebox racket across a wide stretch of Brooklyn.
Gallo was obsessed with the 1947 film Kiss of Death. He studied the character Tommy Udo, a cackling, unpredictable psychopath played by Richard Widmark. He started quoting the character, walking like him, and using the same unhinged energy. Combined with a real capacity for violence, it made him genuinely terrifying.
In 1950, after an arrest, court psychiatrists diagnosed him with paranoid schizophrenia. The label followed him for the rest of his life. He never tried to shake the name Crazy Joe. He wore it like armor.
By the mid-1950s, the Gallo brothers caught the attention of Joe Profaci, the boss of one of New York’s five families. Profaci brought them into the fold and almost immediately put them to work on one of the biggest hits in Mafia history.
On October 25, 1957, Albert Anastasia, the boss of what would become the Gambino family, was sitting in a barber’s chair at the Park Sheraton Hotel in Manhattan. Two gunmen walked in and shot him multiple times. He died in the chair. Joey Gallo later bragged about the hit openly, calling himself and his crew the barbershop quartet.
Gallo expected a serious reward for his role in the Anastasia killing. He wanted a bigger cut of the family’s rackets and more territory. Joe Profaci did not deliver. Profaci was old school, hoarding money and demanding tribute from every member of the family. The Gallos watched him collect while they scraped for scraps.
Joey decided he was done waiting. On February 27, 1961, the Gallo brothers kidnapped four of Profaci’s top men. They grabbed the underboss, the boss’s brother, a caporegime, and a soldier. Profaci himself barely escaped, fleeing to Florida.
Think about the nerve it took. This was a soldier kidnapping his own bosses. In the Mafia, that is a declaration of war.
Profaci’s consigliere negotiated a deal. The hostages were released, and Profaci agreed to give the Gallos better terms. He had no intention of keeping that deal.
On August 20, 1961, Profaci sent men to kill Larry Gallo. Carmine Persico and Salvatore D’Ambrosio lured him to the Sahara Lounge on Utica Avenue in Brooklyn. While they sat at the bar, Persico wrapped a garrote around Larry’s neck and started strangling him. A police officer walked in on a routine check, and the killers fled. Larry survived with rope burns across his throat.
That scene later inspired one of the most famous moments in The Godfather, when Luca Brasi is strangled at a bar.
The Gallo-Profaci conflict raged through Brooklyn for two years. Nine men were murdered. Three more vanished. The Gallos operated out of a three-story brick tenement on President Street in Carroll Gardens, which they called the dormitory. It was here that Joey kept his pet lion Cleo in the basement.
Gallo would bring people down to see the lion. He used it to intimidate rivals. Sometimes he brought Cleo out on a leash.
In November 1961, Gallo was convicted of conspiracy and extortion. On December 21, 1961, he was sentenced to 7 to 14 years in prison. While he sat behind bars, Joe Profaci died of cancer on June 7, 1962. Leadership of the family eventually passed to Joseph Colombo, and the family was renamed the Colombo family.
The Gallos never forgot. And Joey Gallo, locked away in a cell, was about to undergo the most extraordinary transformation of his life.
Most guys go to prison and come out harder and angrier. Joey Gallo went to prison and came out a philosopher. He was incarcerated at Green Haven, Attica, and Auburn. At Auburn, he took up watercolor painting. He worked as an elevator operator in the prison woodworking shop. But the real change happened in his mind.
Gallo taught himself the Evelyn Wood speed reading technique and read everything. Sartre, Camus, Nietzsche, Machiavelli, Kafka. He read up to 10 books at a time. He wrote poetry. He called himself the Walt Whitman of the streets and proposed a book of verse titled Cracked Bricks.
But Gallo did something far more dangerous. At Green Haven, he befriended an African-American drug trafficker named Leroy Barnes, known as Nicky Barnes. Barnes would later become one of the most powerful heroin dealers in Harlem, known as Mr. Untouchable. Gallo mentored him.
Gallo recognized something no one else in the Italian Mafia was willing to see. Black criminal organizations were gaining territory and muscle. Rather than fight them, Gallo decided to ally with them. He coached Nicky Barnes on how to professionalize his operation.
In 1964, Gallo even sued the Department of Corrections after he was punished for allowing a black barber to cut his hair. In a Mafia where black men were not even allowed to enter Italian social clubs, Joey Gallo was building bridges.
During a prison riot at Auburn, Gallo rescued a severely wounded corrections officer from a mob of angry inmates. The officer later testified on Gallo’s behalf at a parole hearing.
On April 11, 1971, after nearly 10 years behind bars, Joey Gallo walked out of prison. Everything had changed. His brother Larry was dead, taken by cancer in May 1968. The family he had gone to war for was now run by Joseph Colombo. Colombo sent a peace offering of $1,000. Gallo laughed and demanded $100,000. Colombo refused.
Before the violence resumed, something strange happened. Joey Gallo became a celebrity.
His first wife, Jeffie Lee Boyd, was a Las Vegas showgirl who lived in Greenwich Village. Through her, Joey entered a world of jazz clubs, beatnik pads, and downtown bohemian culture. He fit right in. He could discuss German expressionism and debate philosophy over cocktails. He was charming, articulate, and genuinely brilliant. He was also a violent criminal who had spent a decade in prison.
That combination was irresistible to the New York literati. Actor Jerry Orbach and his wife Marta became close friends. Ben Gazzara, Peter Falk, Joan Hackett, playwright Neil Simon, and comedian David Steinberg all gravitated toward him. Writer Gay Talese put it simply: he almost became one of the beautiful people.
Gallo loved the attention. He dressed impeccably in pinstripe suits, dark shirts, and white ties. He leaned into the gangster image for his artistic friends.
Meanwhile, Jerry Orbach had just starred in the 1971 film The Gang That Could Not Shoot Straight, based on columnist Jimmy Breslin’s novel about the Gallo crew. Orbach played a character loosely based on Joey himself. The lines between reality and fiction had completely dissolved.
But while Gallo was sipping cocktails with celebrities, the streets had not forgotten him.
On June 28, 1971, Joseph Colombo was shot three times at an Italian Unity Day rally in Columbus Circle. The gunman was a black man named Jerome Johnson, who was killed immediately after the shooting. Colombo survived but was left in a vegetative state. He died seven years later.
Everyone in the underworld looked at the same evidence. A black gunman. An unprecedented hit on a Mafia boss. And Joey Gallo, the only Italian mobster with deep connections to black criminal organizations, had just been released from prison two months earlier.
Whether Gallo actually ordered the Colombo hit has never been proven. Some investigators believe Carlo Gambino orchestrated the whole thing and used Gallo as a scapegoat. But it did not matter what the truth was. It mattered what the Colombo family believed. They believed Joey Gallo had shot their boss.
Carmine Persico, the same man who tried to strangle Larry Gallo in 1961, was positioning himself to take over the Colombo family. He wanted Gallo gone.
Joey Gallo was not hiding. He walked through Little Italy like he owned it. He was working on a book deal with Viking Press. He was meeting with Hollywood producers. Three weeks before his 43rd birthday, he married Sina Essary, a 29-year-old actress.
On the night of April 6, 1972, Joey and Sina joined Jerry and Marta Orbach at the Copacabana to see Don Rickles perform. After the show, the group drove downtown in a black Cadillac. They arrived at Umberto’s Clam House after 4:00 in the morning.
Joey, Sina, his 10-year-old stepdaughter Lisa, his sister Carmela, Pete the Greek, and Pete’s girlfriend sat down. They ordered shrimp, scungilli, and clams. They were between courses when the door opened.
A Colombo associate named Joseph Luparelli had spotted Gallo earlier and alerted members of the crew. Four gunmen walked into the dining room without hesitation. The first shots hit Gallo in the back. He reached for his own weapon. Twenty shots filled the restaurant.
Gallo grabbed the butcher block table and flipped it, creating a barrier between the gunmen and his family. Even with bullets in his body, he moved toward the door. Witnesses said he was trying to draw fire away from his wife and stepdaughter.
He stumbled through the entrance, crossed onto Hester Street, and collapsed beside his Cadillac. Pete the Greek took a bullet in the hip. Carmela screamed. Little Lisa watched everything.
Police arrived minutes later and found Joey Gallo dying on the pavement. He was pronounced dead at approximately 5:00 in the morning on April 7, 1972. His 43rd birthday.
Three days later, at his funeral, his sister Carmela stood by the casket and made a promise the underworld heard. The streets are going to run red with blood, Joey.
She was right. In the months that followed, at least 10 more men were killed in a new wave of warfare between the Gallo faction and the Colombo family. It was the most violent Mafia conflict New York had seen in decades.
The gunmen who killed Joey Gallo were never officially identified. The leading theory points to a Colombo hit squad. Mob enforcer Frank Sheeran, who later claimed to have killed Jimmy Hoffa, also took credit for shooting Gallo. Most mob experts doubt his claim.
In 1975, three years after the killing, Bob Dylan was visiting the home of Jerry and Marta Orbach. He saw a painting of Joey Gallo hanging on the wall and asked about it. What the Orbachs told him inspired Dylan to write an 11-minute ballad called Joey, which appeared on his 1976 album Desire.
The song paints Gallo as a romantic anti-hero. Dylan later said he never considered him a gangster, but rather an underdog fighting against the elements. The song was not universally loved. Rock critic Lester Bangs called it repellent romanticist trash.
Joey Gallo was responsible for a conflict that killed over a dozen men. He terrorized business owners with knives. He was convicted of extortion. But he also read Camus. He painted watercolors. He saved a prison guard’s life. He tried to build alliances across racial lines that no one in the Mafia had ever attempted.
The truth about Joey Gallo does not fit neatly into a category.
His brother Albert survived the wars and eventually faded from public life. Nicky Barnes went on to become one of the biggest heroin dealers in American history before becoming a government informant. Jerry Orbach went on to become Detective Lennie Briscoe on Law & Order. Sina Essary took her daughter Lisa and moved to Tennessee. Lisa grew up to become a casting director in Hollywood.
Carmine Persico eventually became boss of the Colombo family and spent most of his life in prison.
Joey Gallo spent 43 years trying to be something the Mafia could not contain. He wanted to be an intellectual, a revolutionary, a celebrity, a kingmaker. He wanted to tear down the old order and replace it with something that crossed racial lines and cultural boundaries.
The Mafia does not reward visionaries. It eliminates them.
He died eating scungilli at 4:30 in the morning on his birthday. A lion tamer with no lion left. A philosopher who ran out of arguments. A man who almost became one of the beautiful people, buried instead with bullets in his back.