After his parents’ divorce, Itzler moved to New York with his mother, whom Jason describes as “the hottest mom in the world. She had this Mafia princess–Holly Golightly thing about her. Her vanity license plate was TIFF. My mother being beautiful made me into who I am today, because when you grow up around a beautiful woman, you always want to be surrounded by beautiful women.”
Also a big influence was his mom’s father, the semi-legendary Nathan Lubell, “the biggest bookmaker in the garment industry, a gangster wizard,” says Jason. “He owned a lot of hat stores, a bunch of the amusement park in Coney Island, and was hooked up with Meyer Lansky in Las Vegas hotels. I used to love it when he took me to the Friars Club, where he was a king. Even as a kid, I could feel the action.”
With his mom remarried, to Ron Itzler, then a lawyer in the firm of Fischbein, Badillo (as in Herman), Wagner, and Itzler, the family lived in the Jersey suburbs. Displaying his compulsive intelligence by setting the all-time record on the early-generation video game Scramble, Jason, “pretty much obsessed with sex from the start,” wrote letters to Mad magazine suggesting it put out a flexi-record of “teenage girls having orgasms.” Summers were spent in the Catskills, where as a cabana boy at the Concord Hotel he befriended people like Jason Binn, now the playboy publisher of the Hamptons and Los Angeles Confidential magazines, a name Itzler paid homage to with his NY Confidential.
Itzler remembers, “At the Concord, when Jason Binn said he was the son of a billionaire, and my stepfather told me, yeah, he was, I got light-headed.”
In the late eighties, after getting through George Washington University, even though he was “mostly running wet-T-shirt contests,” Itzler entered Nova Southeastern University, a bottom-tier law school in Fort Lauderdale, Florida, where he embarked on what he calls “my first great chapter” as “the 22-year-old phone-sex king of South Beach.” Advertising a “Free Live Call” (after which a $4.98-a-minute charge set in), Itzler’s company was doing $600,000 a month, hitting a million and a half within a year.
“I had so much money,” Jason recalls. “I bought an Aston Martin Virage, 300 feet of oceanfront property. Like a moron, I spent half a million decorating a one-bedroom apartment.”
Alas, it would all soon come tumbling down, owing to what Jason now calls a “kind of oversight,” which left him owing $4.5 million at 36 percent interest. Forced to declare bankruptcy in 1997, he lost everything, including his visionary acquisition of one of the fledgling Internet’s most valuable URLs: pussy.com.
The demise of Itzler’s phone-sex company set a pattern that would be repeated in 2000 with his next big act, the SoHo Models fiasco. With typical overreach, Jason rented an 8,000-square-foot space at the corner of Canal and Broadway and declared himself the new Johnny Casablancas. Unfortunately for the young models hoping to find their faces on the cover of Vogue, the true business of SoHo Models was to supply Webcam porn. For a fee, the voyeur would type in “take off blouse . . . insert dildo.” Squabbling among gray-market partners soon ensued. Within months, Jason found himself dangling over the side of the Canal Street building, held by the ankles by a guy named Mikey P.
Jason says he would have gotten through these setbacks more easily if his mother were still alive, but Ronnie Itzler died of cancer in 1994, “after which I went kind of a little nuts.” Following the collapse of the phone-sex firm, he twice attempted suicide, once running himself through with a steak knife and on another occasion drinking “a milk shake” he claims contained “75 Valium, 75 Klonopin, and a couple bottles of Scotch.” Much to his surprise, he survived both times.
Desperate for money after the SoHo Models disaster, Itzler decided his best option was to go to Amsterdam to buy 4,000 tabs of Ecstasy. “In retrospect, it was a totally retarded idea,” says Jason, who would leave Newark airport in handcuffs. He was sentenced to five years in the Jersey pen. The fact that his grandfather, whom he’d idolized as a gangster, stopped talking to him when he got locked up “was hard to take.”
“Jail is terrible, really boring,” says Jason. “But it does give you plenty of time to plan your next move.”
On parole after serving seventeen months of his smuggling sentence, living in a funky third-floor walk-up in Hoboken per the terms of his release, Jason started NY Confidential (he would remain on parole his entire pimp career) in late 2003. Business was spotty at first but picked up dramatically in early 2004, when Natalia walked into the company’s place at 54th Street and Sixth Avenue, an office previously occupied by the magician David Blaine.