Crazy Joey Gallo's Widow Reflects on being Married to the Mob

Friends of ours: Joey "Crazy Joey" Gallo, Joe Profaci, Albert Anastasia, Jackie “Mad Dog” Nazarian, Joe Colombo, Bobby Bongiovi, Sam Wuyak

When gunfire erupted in Umberto’s Clam House, Sina Essary watched her husband of three weeks throw over the dinner table, absorb three bullets to his frail body and stumble out into Mulberry Street to die. It was April 7, 1972, in New York’s Little Italy, and Sina’s husband was no ordinary victim. He was Joey Gallo—“Crazy Joey,” they called him—an intellectual and charismatic kingpin of the New York rackets.

Today, largely unknown among her neighbors, Sina lives on a small farm in rural Leiper’s Fork, surrounded by a barn full of horses and rescued dogs and cats. Most people know her, she says, only as “that crazy woman from New York who keeps all those animals on her place.” Now 65, she has an elfin stature and a rich, resonant voice that carries just a trace of a New York accent. She is a commercial photographer by trade—trained at New York’s famed New School for Social Research—and she keeps her life very quiet and private. But in the early 1970s, at the height of gangster chic, the petite woman with the snapping dark eyes was at the center of a maelstrom. She was both a celebrity and a target. As the wife of one of New York’s most feared—and most glamorous—mob bosses, she lived among superstars and triggermen in a cosmopolitan jungle where wealth and power went hand in hand with bloody retribution. The tabloids took her picture when she became a bride. Less than a month later, they took her picture when she became a widow.

Now, safely sequestered among the peaceful hills of Williamson County, 35 years after her husband’s murder, Sina has decided for the first time to tell the story of her life with Joey Gallo. “I haven’t told it before,” Sina Essary laughs, firing up a Benson & Hedges and fending off her three-legged cat, “because I’ve been too busy wiping horses’ asses on the farm. But I’ve been writing my memoirs in my head while I’m shoveling manure!”

Sina began her adventurous life as a pregnant nun. No kidding. She attended Catholic schools and entered the convent of the Sisters of St. Joseph when she was only 18. “I was very, very religious as a youngster,” she says. While Joey Gallo was growing up to join the New York syndicate, Sina was preparing to take her final vows of poverty, chastity and obedience.

Outside the convent walls on a sick leave, however, she got together with an old boyfriend. “Before you knew it,” she says in her deep chuckle, “I wasn’t a virgin anymore.” She became pregnant from that single encounter and her short life in the convent was over.

Sina married the old boyfriend, had a child with him, divorced him and found herself a single mom working in a jewelry store. But her daughter, Lisa Essary, now a Hollywood casting director, was a theatrical prodigy. She soon became a child star on Broadway, changing Sina’s life for the better.

As Lisa’s career grew, Sina fell in love with Lisa’s music coach, a man who was destined to become a conductor of the New York City Opera and the Houston Grand Opera. She wanted desperately to marry him—she still calls him “the love of my life”—but she adds with a laugh, “What I didn’t know was he was gay!”

With a track record like that, it was perhaps inevitable that the nun would become a gangster’s moll.

Joey Gallo was a Brooklyn kid, the son of a loan shark and would-be rumrunner. A 1973 book by Harvey Aronson, The Killing of Joey Gallo, chronicles his violent rise through the ranks of the mob. He became a career criminal at a very early age, and though he was arrested many times as a youth, he was never sent to prison. He was convicted only once—for burglary in 1950—but when a court psychiatrist declared him paranoid-schizophrenic, Joey received a suspended sentence.

Joey had flair. In 1947, he saw Richard Widmark in the film Kiss of Death, and with his drowsy, heavy-lidded appearance Joey began to pattern himself after Widmark’s giggling psycho Tommy Udo. He began to dress and act like Udo and could recite long passages of the movie’s dialogue. But despite his theatrical posturing, Joey was still a violent and deadly man. Writing after Joey’s death, the legendary New York Post columnist Pete Hamill said of the young Joey:

“He might have been a fresh twenty-one-year-old kid dressed in a zoot suit, but the eyes were ancient…eyes devoid of time or any conventional sense of pity or remorse…. [H]e would joke with the cops and smile for the reporters, but the eyes never changed…tormented eyes.”

In 1957, Joey became a “made” man in the Joe Profaci organization by (it was said) assassinating Albert Anastasia, one of Profaci’s enemies and boss of the notorious “Murder Incorporated.” According to witnesses, Anastasia was having his hair cut in a Sixth Avenue hotel when two disguised gunmen rushed through the hotel lobby. They shot Anastasia dead in his chair and escaped into the crowd. No one was ever charged with Anastasia’s killing, but the story on the street was that the shooters were Crazy Joey and an accomplice named Jackie “Mad Dog” Nazarian. Tommy Udo would have been proud.

Profaci’s business was run by coercion, and Joey was his top enforcer. Multiple beatings and murders were attributed to Joey during the late 1950s, and Time magazine claimed that he stabbed one target to death with an ice pick. But nothing against him was ever proven. The Mafia code of omerta—silence—protected Joey among his own.

In time, though, Joey became disenchanted with the way Profaci was dividing the family profits. So along with his two brothers and several other Profaci henchmen, he converted a Brooklyn warehouse into a fortress and launched a revolt. As the 1950s came to a close, a gang war raged between Joey and Profaci. It was an onslaught of killings, beatings and kidnappings. It was also successful. In the end, Joey succeeded in wresting away a significant part of Profaci’s holdings.

Joey built his winnings into a small empire based on violence and extortion. For years he evaded punishment. But finally, in 1961, he was taken down for threatening to kill a Brooklyn bar owner. He was convicted of extortion and sentenced to seven to 14 years in prison. The judge who sentenced him said that Joey “[has] an utter contempt for the law and is a menace to society.”

Joey’s time in prison was marked by the Attica riots, which he helped to settle, and at least two mob attempts on his life. But he spent most of his time profitably. He set out on a project of self-education, becoming a fine painter and reading history, art, politics and philosophy.

Then in 1971, after serving almost 10 years, Joey was released and began parlaying his newfound education and refinement into a fresh image around New York. Tommy Udo was gone. In his place—as far as the outside world could see—was a well-mannered and intelligent man.

That’s when he met Sina.

Even though she grew up in a large Italian American community, Sina knew very little about the Mafia. Born into a close-knit family in Ohio, she grew up in comfortable circumstances. She attended private Catholic schools. She lived a somewhat sheltered life.

Sina’s maternal grandfather had come to America from Bari, Italy, an old city on the Adriatic coast, and developed a thriving Italian grocery business. Her maternal grandmother became famous in America for hosting a popular radio show called The Italian Hour—all Italian opera and popular songs—every Sunday afternoon.

Her aunt Dorothy attended Juilliard and later sang with the San Francisco Opera. “I was raised listening to opera,” Sina says. “My earliest recollection as a baby was hearing my aunt sing ‘Un bel di’ to me in my high chair. Even today I keep Live From the Met and WPLN playing in the barn to keep the horses company.”

Sina’s only exposure to organized crime came from a family legend she heard from her grandparents. After her grandfather’s business began to prosper, she says, figures from a local syndicate came to him and demanded that he surrender part of his business as tribute. He refused. As a result, both he and Sina’s grandmother were beaten. Her grandfather stood firm, however, and eventually the gang gave up. He had a strong temperament, and Sina inherited it.

In due course, Sina and Lisa moved to New York and quickly became well known on Broadway. Lisa landed big parts in a number of plays, and the two of them became friends with some of the biggest names in show business. Soon Lisa was attending private schools, and they moved into the penthouse of an upscale apartment building at the corner of Fifth Avenue and 15th Street.

Life was good. Sina never dreamed she was about to meet, and marry, a man like Joey Gallo.

While Joey was still languishing in prison, his old enemy Joe Profaci died. Control of the Profaci mob passed to Joe Colombo, one of the “new” Mafia dons who knew something about politics and public relations. He formed an organization he called the Italian American Civil Rights League and used it to rally support against the FBI’s claim that he was a mobster. With the league as his mouthpiece, Colombo maintained that there was no such thing as “the Mafia” and that he was “just an honest businessman.” The league was hugely successful and so powerful that Colombo was able to win concessions from the producers of The Godfather about the way Italian Americans were portrayed in the film.

The Profaci organization’s racketeering remained profitable too, but many of Colombo’s subordinates were bridling at the way he ran the business and divided the spoils. To his hardened street enforcers, Colombo was a lightweight and a publicity seeker. Dissension in his family was building.

Into this unsettled world, Joey arrived fresh from prison, bearing a 10-year grudge against the Profaci family. Joey might have been flashing his new cleaned-up image in public, but in secret he was re-energizing the Gallo gang. He planned to depose Colombo. Less than six weeks after his release from prison, Joey demanded a $100,000 tribute payment from Colombo as a condition for staying away from his business. Colombo refused to pay. Instead, he placed a contract on Joey’s life.

On June 28, 1971, just four months after Joey’s release from prison, Colombo held a rally of his Italian American Civil Rights League in Columbus Circle, just off Central Park. Thousands of people attended the noontime affair. But as Colombo began making his way to the dais to speak (along with the mayor and several other luminaries) he was shot and severely wounded by a black man later identified as Jerome Johnson.

No one ever discovered who Johnson was working for. As fate would have it, he was immediately shot and killed by yet another never-identified gunman. Colombo was left in a near-vegetative state and was off the board as far as the rackets were concerned. The event made the cover of Time magazine the following week.

Joey claimed that the FBI was behind the Colombo attack, but most reasonable minds concluded that Joey had engineered it himself. He had a clear motive, and he was certainly capable of pulling it off. While the police and FBI looked for clues, the heirs to Colombo’s power renewed the contract on Joey’s life. By July 1971, one month before he met Sina, Joey had less than a year to live.

The obvious question is why a respectable former nun like Sina Essary would fall for a mobster with a price on his head. Sina chuckles and says, “The story is kind of complicated.”

Sina first saw Joey on her apartment building’s elevator. She lived in the penthouse and Joey happened to live in an apartment downstairs. Joey was smitten by Sina, but she was not immediately attracted to him. The first few times she encountered him, with his retinue of bodyguards, she says he appeared “extremely frail and pale. He looked like an old man. He was a bag of bones.” What Sina didn’t know was that Joey still bore the marks of 10 years in prison.

Still, Sina says, Joey had an attractive aspect. “You could see the remnants of what had been a strikingly handsome man in his youth,” she remembers. “He had beautiful features—beautiful nose, beautiful mouth and piercing blue eyes.”

Joey also had a special charisma, she adds. “People were mesmerized by him,” she says. “He had that quality that attracted people to him, no matter who they were. He was extremely intelligent and he could talk about anything. He could talk about art, theater, politics, philosophy—all the things he had been reading about in prison.”

Joey launched an immediate pursuit of Sina, even though he had recently remarried his former wife, Jeffie. “She looked like a movie star,” Sina says. But nothing stopped Joey, and during the following weeks he began to win Sina over with gifts and plates of Italian food. Before long, their children were playing together and Sina was having dinner at Joey’s apartment. Because Joey was married, Sina felt safe from a more complicated relationship.

Sina gradually learned of Joey’s past, but he told her he wasn’t in the rackets anymore. He still carried bodyguards out of necessity, he said, but he was no longer strong-arming anybody. “It didn’t bother me much that he had been in the Mafia,” Sina recalls. “He told me he was through with the mob. I thought, so what, this is New York, so he’s in the mob, big deal. I didn’t realize who he actually was until I married him and had my picture in the newspaper!”

What Joey really wanted, Sina says, was to get into show business. Several years earlier, Jimmy Breslin had written a comic send-up of the Mafia called The Gang That Couldn’t Shoot Straight, supposedly based on Joey and his gangland pals. The book spawned an equally popular movie starring Jerry Orbach—that’s right, the same Jerry Orbach who played Lenny Briscoe on Law & Order—as a Joey-like character named “Kid Sally Palumbo.” Joey didn’t like the way the film portrayed him, but he liked Orbach and wanted a meeting. They quickly became friends, as did Sina and Orbach’s wife Marta.

From that point forward Joey was hooked on celebrities, and before long they were hooked on him too. There was an aspect of danger about Joey that appealed to show business people. Being with Joey gave them a vicarious sense of living the romantic life depicted in The Godfather, which had just opened to acclaim and unprecedented box office. The movie ushered in an intense new public fascination with the underworld. Joey exuded excitement, and people loved it. “He loved walking into Sardi’s,” Sina recalls. “You could hear a pin drop when he came in.”

In addition, many people knew about the Colombo hit and the possibility that Colombo’s soldiers might try to kill Joey. That gave his relationships with friends an unusual intensity. Orbach told Time magazine, “Joey compressed time with us because he knew…he might not have much time, that he could go at any minute…. [A] minute talking to Joey was like an hour spent with someone else…. It was startling to talk with him.” Women were particularly drawn to Joey’s fatal aura. “Joey was a terribly sexy person,” Marta Orbach admitted to Time. Even highbrow critic Susan Sontag wanted to meet him.

Pretty soon the former nun and the gangster became lovers. Sina was a beautiful 29-year-old, and Joey had just spent 10 celibate years behind bars. For Sina’s part, she says, “Part of me was craving that sexual thing which I hadn’t had for 10 years. I’d been divorced for 10 years and all the men I ever hung around with were gay!”

Joey soon began insisting that they get married and, after Joey sent Jeffie packing, they did. The wedding was held in the Orbachs’ apartment in March 1972. “The ceremony was performed by the same pastor who had married Tiny Tim and Miss Vicky on the Johnny Carson show,” Sina says, laughing. Joey’s best man was the comedian David Steinberg, and the small ceremony was reported the next day in the pages of the New York Post and the New York Daily News. But in three weeks Joey would be dead.

Not long after the ceremony, Sina began to realize that Joey was not entirely free of his past. On April 5, 1972, three weeks after the wedding and two days before Joey died, the apartment building’s doorman buzzed Sina to say that a deliveryman was in the lobby with a package for her. Sina told the doorman to send the man up, but when Joey overheard her he got angry. At his instruction, two of his bodyguards intercepted the deliveryman at the elevator and attacked him, pulling a gun and choking him. “Joey feared that the package contained a bomb,” Sina says, “but it turned out to be a Tiffany ice bucket for me from the producer Bruce Jay Friedman.”

Joey blew up at Sina, throwing her into a chair and raging at her. He screamed at her never to do something like that again, with a ferocity that Joey’s associates in the mob knew well. For Sina, it was an abrupt and terrifying wake-up call. “I didn’t know this was part of the deal,” Sina says. “I realized there was something I didn’t know about going on, there was something bigger than me. That was the day I knew it was over, that I couldn’t live like that.” So she threw Joey out of her apartment. “If this is what my life with you is going to be,” she told him, “you have to leave.”

The following day, however—April 6, 1972—was Joey’s 43rd birthday, and there was a celebration planned at the Copacabana with the Orbachs, Steinberg, comedian Don Rickles and Joey’s usual crowd of celebrities and hangers-on. Still intending to leave Joey, Sina nevertheless relented and agreed to go to the party with him.

Late on the evening of the 6th, Joey’s group picked Lisa up from her performance in Voices at the Ethel Barrymore Theatre (she had third billing behind Julie Harris and Richard Kiley), and they drove to the Copa. It was a great night. Rickles introduced Lisa from the stage, and everyone sat and drank champagne until almost 4 a.m. Then the Copa closed and they all went in search of breakfast.

The party now consisted of Joey, Sina and Lisa, along with Joey’s sister and a single bodyguard, Pete “The Greek” Diapoulos. Another bodyguard, Robert “Bobby Darrow” Bongiovi, had left earlier in the evening with a woman from the Copa. By then, it was early morning, April 7, 1972.

The search for breakfast took them to Umberto’s Clam House at the corner of Hester and Mulberry streets in Little Italy. No one in the party had been to Umberto’s before, but it was the only place open at that hour. “We were all sitting around a big heavy table, with Joey facing the door and Lisa and I sitting next to the wall,” Sina remembers. “Joey thought the food was excellent and ordered seconds for everybody.”

Without warning, several gunmen burst through the door and began firing. Accounts vary as to how many shooters were involved, but Sina swears there were five. Colombo’s wiseguys had apparently seen Joey going into the restaurant and had rounded up some of Colombo’s soldiers to put him away.

When the shooting started, Joey turned the table over to protect the others while Sina dragged Lisa to the floor and covered her with her coat. In a matter of seconds, more than 20 shots were fired. Joey was struck three times—in his arm, his spine and finally in his carotid artery. He staggered out the door, followed by his assailants’ fire, and collapsed on the pavement. When the shooting stopped, there were 17 bullet holes in the wall behind Sina’s and Lisa’s chairs. Joey lay dying in the street.

“Joey had an intense sense of destiny,” Marta Orbach says. “If he was truly marked for dying, this old-fashioned way—in style—would have been a point of honor with him. Joey’s death would have appealed to his sense of drama.” Pete Hamill called it “a supreme New York moment.” But for Sina, huddled with her daughter on the floor of a restaurant filled with shells and screams and blood, it was anything but supreme.

“I thought I was observing all this through the eyes of death,” Sina says today. “In fact, I thought I was dead.” Her next thought was an irony that struck her in light of their earlier fight. “Fancy that,” she thought, “somebody was trying to kill him. My God, he wasn’t kidding!”

Today Sina tells her stories in the living room of her modest farmhouse, surrounded by photographs of her family and friends. These include a prominently placed picture of Joey. At 65, she still retains her classic Italian beauty and charm. She lives alone and maintains only a few close friendships. Hearing her relate her stories in the quiet of her living room or outside her sunny barn is a surreal but wholly believable experience.

Sina came to Tennessee in 1991 to get away from her notoriety. She says she had become almost a novelty in New York. “I wasn’t introduced to people as Sina Essary anymore,” she says. “I was ‘Joey Gallo’s widow.’ I had become like a stop on a sightseeing bus, like the Statue of Liberty or something.” She was besieged with requests for interviews in New York, all of which she declined. She even turned down an invitation to appear on The Tonight Show With Johnny Carson.

But she had good reasons to keep quiet. One, she says, was the possibility that she herself might be marked for murder. She had been a witness to Joey’s shooting, after all, and might have identified the killers. For a long time afterward, she was followed by FBI agents, the NYPD and members of the Gallo gang in what she calls “an unholy alliance” to protect her from the Colombo crew. After a while, it all became too much for her.

For Sina, the attraction of Tennessee was its entertainment business. “I felt I could practice my photography in Nashville,” she says. “I had been in the business of photographing celebrities in New York, so I figured I could do it in Tennessee too.” She is presently planning a retrospective show at the Nashville Design Center in Melrose, where she intends to represent the large portfolio of pictures she has amassed over the years. In perhaps the richest irony of all, she photographed a young actress who would play the most famous Mafia wife of all: Edie Falco, who stars as Carmela on The Sopranos.

Sina admits that her move to Tennessee was also an act of “menopausal madness” which in some respects she still regrets. “I had always planned to go back to New York,” she says. “I had my box at the Metropolitan Opera, my rooftop rose garden and, of course, all my friends. For three years after I moved here I kept my apartment on Fifth Avenue, thinking I might go back. But when I bought my first pregnant mare, I fell so in love with her baby foal that I knew I could never leave. I still love New York, and I cry when I think about it, but I love my horses more.”

Sina has no fear from the Mafia today. Those days have passed, and the principal actors have died. She still speaks and corresponds every month with the only remaining member of the Gallo gang she knows, Bobby Bongiovi, the bodyguard who left early on the night Joey was killed. Bobby, movie-star handsome in his youth, is old, sick and now serving a life sentence in Dannemora for the murder of another mobster, Sam Wuyak, the year after Joey died. Bongiovi denies killing Wuyak, but he told Sina, “There is plenty of other stuff they could have sent me up for.” According to press accounts, when Bongiovi received his sentence at the hearing, Sina Essary was there, brushing away tears.

Joey’s life has been written about a number of times, but the accounts have not always been consistent. Some facts are hard to come by, and arguments about Joey still simmer among scholars of the Mafia life. Perhaps the most comprehensive treatment of Joey’s career is the Aronson book, though Sina says that it too contains errors. But Joey’s death only hastened his passing into myth. In 1974, Italian director Carlo Lizzani made a biopic called Crazy Joe starring the young Peter Boyle as Joey, with Eli Wallach, Paula Prentiss and even Henry Winkler in supporting roles. It was a spaghetti-Western take on gangland life, but critic Jerry Renshaw called it a gem—“a rawer Scorsese without the polish or panache, relying instead on pungent dialogue and gritty performances.”

By 1976, the fallen mobster had been rehabilitated as the romantic hero of “Joey,” from Bob Dylan’s 1976 album Desire—a combination Tom Joad and Pretty Boy Floyd whose “closest friends were black men ’cause they seemed to understand / What it’s like to be in society with a shackle on your hand.” In 1993, soon after Sina’s move to Nashville, Dylan even paid a visit to her home. They spent an afternoon discussing life in New York, shared acquaintances—and, of course, Joey.

More measured accounts of Joey’s life have revised the romantic image he carried while he was alive. He was a man capable of ruthless, and remorseless, brutality. His war with the Colombo family continued for a long time after he died, and several more killings took place, including those of two innocent people. The ferocity of the gang war caused Jimmy Breslin to change his thoughts about the rackets, writing that he considered The Godfather “hardcore pornography” and his own The Gang That Couldn’t Shoot Straight “the product of demented thinking.”

Still, Sina has no regrets about marrying Joey. “It’s part of life,” she shrugs.

Joey’s funeral was huge, front-page news in all the papers. Pictures showed Sina and Lisa, grieving, standing on the steps of the church. The local parish priest refused to bury Joey—whether for doctrinal reasons or fear of Colombo mob reprisals was never made clear. So Sina arranged for a substitute priest to fly in from Cleveland to conduct the service.

Along the route to the cemetery, the sidewalks were jammed with people paying their respects to Joey Gallo. They strained to catch just a glimpse of his gleaming copper casket. Because of the attendance of so many gangland figures, police lined the streets and the rooftops to head off further violence.

Looking back, in the faraway seclusion of her Williamson County farm—a lifetime ago from the vendettas and tangled allegiances of Little Italy—Sina Essary says the procession would have appealed to Joey’s sense of show business. Tommy Udo was dead, and Sina says, “You would have thought the Pope was passing by.”

A former nun should know.

Thanks to Wayne Christeson