Hip-Hop Poseur Jimmy Sabatino Can't Stop Scamming — Even From Prison

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Sabatino doesn't mind saying he's a criminal, but a sex offender? He mulls the allegation day and night, sifting for holes in the state's case, but even South Florida's most notorious con man may not be able to talk his way out of this one.

At civilization's edge, where exurbs meet Everglades, the sun had just fallen behind the trees around Metro West Detention Center when Jimmy Sabatino, wearing beige Crocs, clacked into a room full of windows. It was a slow, painful movement. The still-young man leaned upon a steel, four-pronged cane, and a faint wince came across his face. The elastic around his extra-large orange prison pants was too loose, and every few steps, he had to hitch them up.

Despite Sabatino's remarkable track record of getting people to do whatever he wants, he is not a classically handsome man. A delicate, upturned nose anchors a melon-shaped face. His hair, what little is left, easily adopts a greasy shine, so he normally sweeps it back. His health vacillates from bad to worse. He's diabetic and seizure-ridden, and four strokes have left him with a pair of crooked brown eyes so lazy they're practically asleep.

"Who's this?" Sabatino barked at a reporter he'd been expecting for days, eyes swiveling wildly behind a pair of thick glasses. "Who's this?" Then, for a man as loquacious as Sabatino, he did something unexpected: He shut up. "Sign a piece of paper right now saying this is off the record or else I won't talk," he said. Once demand was denied, he pulled up his pants, gripped the cane, and limped out of the room.

Jimmy Sabatino almost never turns down an opportunity to talk about Jimmy Sabatino. During hours of interviews with New Times over the telephone before this recent October meeting, Sabatino couldn't stop talking, even when family and legal counsel advised him to stop. For Sabatino, it's like a tic. If there's attention to be had, he has to have it.

Born in 1976, Sabatino grew up in the Brooklyn neighborhood of Bensonhurst, raised by a loving father named Peter Sabatino. Beyond that, Sabatino is reluctant to give any more specifics. Did he have any siblings? "I was an only child," Sabatino says. "Just me and my father." Did he graduate high school? "I went to St. John's Villa before graduating from industry school." What's the word on his mom? "She's dead. I don't know anything about her. I never had a mother. My father was both my mother and father."

But those claims are all untrue, according to family members and federal documents. Sabatino, whose family has ties to organized crime in New York, never graduated high school, and he was not an only child.

He has a brother and a sister, and his mother was very much in the picture. At least at first. With dark Italian looks, Madeline Sabatino was enamored of show business. She did everything she could to get onto the big screen but was mired in "B movies," claimed Peter Sabatino. Her biggest role was a bit part in 1971 in The French Connection with Gene Hackman. "She had always had aspirations of being famous but had never really made it as far as she wanted," Peter Sabatino wrote in a letter to a New York federal judge in 2003 in support of his son. "When James was born she projected all of her dreams of fame and fortune onto her son."

She thrust Sabatino and his sister, Dawn, into the modeling business, where both thrived in the New York market. Sabatino spent every moment with his mother. But his father, whom federal documents describe as a onetime "liaison" to the Gambino crime family, was troubled by the work. One day, when Sabatino was 7, the mother and son "arrived home one day from a modeling shoot," recalled the senior Sabatino. "You could hear the kids playing baseball outside. James ran to the window and turned to me and asked, 'Daddy, what are those kids doing?' I was dumbfounded." The father realized his wife's aspirations for stardom were costing his son's childhood. He canceled the modeling shoots.

His wife took it hard. "She always had problems with alcoholism," Peter Sabatino wrote. "It worsened as James aged, and her career dwindled. After I put an end to James' modeling, she turned inward and withdrew from life and James." When he turned 11, James came home from school one day to find an empty house. His mother was gone; she left a note saying she wouldn't return. "Not only did she not return," his father lamented, "but she never called or wrote."

James internalized the abandonment, but it soon manifested itself in strange and disturbing ways. Weeks later, Peter Sabatino got a call from a concerned teacher of his son's. The boy had told her his mother had died in a car accident. "It was his way of resolving the matter," his father wrote. "And from that moment, James' antics would only escalate." He was expelled from 12 schools over the following years and tore through a smattering of baffled therapists. At age 12, he clocked 30 days at the Staten Island Psychiatric Facility and was later diagnosed with an impulse control disorder that, according to a psychological report, "was unlikely to change in the near future."

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Terrence McCoy