Itzler was born Jason Lubell Sylk, the only son of Ronnie Lubell and Leonard Sylk. Leonard Sylk's father, Harry Sylk, built a great fortune from his Sun Ray Drugstore. He also owned part of the Philadelphia Eagles. Jason spent his early years in Philadelphia. But following his parents divorced, Itzler moved to New York with his mother, who he cites as his greatest inspiration. Jason lost her to cancer in 1994. Another big influence for Jason growing up was his mother's father, Nathan Lubell, who was in the garment world and a big bookmaker. Jason's mother eventually remarried Ron Itzler, a then prominent lawyer in the firm of Fischbein, Badillo, Wagner, and Itzler, and so the family moved to the suburbs of New Jersey. Growing up, Jason attended a number of private schools, including the Elisabeth Morrow School, the Dwight-Englewood School, and Hotchkiss School, but graduated from the public Tenafly High School. Jason spent many of his summers in Catskills, where he worked as a cabana boy at the Concord Hotel. There he became familiar with the ultra-rich. Jason graduated from George Washington University with degrees in Political science and Art history. He was also a member of the fraternity, Zeta Beta Tau.
In the late 80s, Itzler, entered Nova Southeastern University, a law school in Fort Lauderdale, Florida. While there he started a phone sex operation called M2 Communications, Inc., where he would charge $4.98-a-minute. The company did well, averaging $600,000 a month. Due to mismanaging, he wound up owing $4.5 million and was forced to declare bankruptcy in 1997. His next company was called SoHo Models. Jason rented an 8,000-square-foot loft on the corner of Canal and Broadway in New York City to supply Webcam porn. The partners involved could not agree on the direction of the company and Jason was again saddled with a huge debt.
New York Confidential
Jason Itzler started New York Confidential, an online escort service that claimed to guarantee satisfaction, in late 2003, while he was on parole from prison and forced to live in Hoboken, New Jersey. New York Confidential was run out of Itzler's parolee apartment in Hoboken. The company was doing well and the office was moved to 79 Worth Street in Manhattan. In 2004 Itzler was averaging a gross of $25,000 a night. Itzler says, he cared more than anyone to create the right atmosphere for his customers. "That's because we were the best," said Itzler. "At NY Confidential, I told my girls that the pressure is on them because we have to provide the clients with the greatest single experience ever, a Kodak moment to treasure for the rest of their lives. Spreading happiness, positive energy, and love,that's what being the best means to me. Call me a dreamer, but that's the NY Confidential credo."  It was this attention to detail and customer satisfaction that made the group successful, attracting a wide array of clients, including senators and famous athletes. There were even talks of franchising Confidentials in other cities, such as Las Vegas.
Itzler has been engaged 9 times. He has dated and married his own work girls including the number one escort girl, Natalie McLennan, known as Natalia. Natalia made as much as $2,000 per hour with a two-hour minimum working as an escort at New York Confidential. Asked if the work affected her relationship with Itzler, Natalia says he would sometimes get jealous of the time she spent away from him, but not of the men. It would only bother him if she slept with another man for free. In 2010, Natalia pleaded guilty to a charge of attempted money laundering in connection to New York Confidential. He was also married to Elisa Bridges, a Playboy centerfold. Itzler has "King Pimp" tattooed on his arm.
Criminal charges and trials
Itlzer was convicted in 2003 of trying to smuggle the drug ecstasy into Newark Liberty International Airport from Amsterdam. From 2003 to 2004, he ran the New York escort agency "New York Confidential" for wealthy clients. In 2005, Itzler was convicted of money laundering and promoting prostitution, and sentenced to 18 months in prison. Itzler later claimed that Ashley Alexandra Dupré, the call girl connected to the Eliot Spitzer prostitution scandal, had previously been an escort with "NY Confidential".
In September 2011, he was arrested and accused of providing a prostitute and $4,700 worth of cocaine to a customer for three days at the Trump International Hotel at Columbus Circle. He was incarcerated on $500,000 bail (then reduced to $200,000) pending trial. He retained Mark Jay Heller, who represented the Son of Sam serial killer David Berkowitz with a promise of payment from future earnings from a film that may be made about his life by Polsky Films.
In April 2012, Heller negotiated a deal with prosecutors for a four years sentence, however, on May 8, 2012, Itzler went before Justice Thomas Farber felt that Heller coerced him into agreeing to pay $420,000 for representing him. Judge Farbeer told Itzler, "you don't have a penny to your name at this point," however, Itzler is purportedly supposed to receive the money if a film is made about his life from Polsky Films. He then announced that wanted to fire Heller because he had read a 2010 profile of Heller and realized that he had been wrongly treated. "I don't trust Heller!" Itzler shouted. "Heller to me is the Devil!"
Justice Farber said Heller had negotiated "an extraordinarily generous offer" for Itzler. The judge, nonetheless, allowed Itzler to fire Heller and hire a new lawyer, Michael Marley, a former sports columnist for the New York Post and a publicist for the boxing promoter Don King.
On May 14, 2012, Itzler was sentenced to four years in prison for promoting prostitution, money laundering and drug charges, but not before he called for the legalization of prostitution. "In Nevada, the saying is, 'If it doesn't scare the horses, who cares?'" he told Manhattan Supreme Court Justice Thomas Farber before being led away in his handcuffs and black velvet jacket. "I predict here and now that eight years from now, in the year 2020, New York and other enlightened states will decriminalize the world's oldest profession, namely prostitution," he said, ending his statement with, "And I'd like to give a shout-out to Billy Ray Cyrus!" Itzler had mistakenly believed that the alleged john in the case – a Pennsylvania man who paid Itzler $19,500 for a cocaine and hooker binge at the Trump International Hotel last year – was country singer Billy Ray Cyrus using an alias.
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- Marcus, Stephanie (2011-09-14). "'King Pimp' Jason Itzler Alleges Billy Ray Cyrus Conspiracy Theory In Court". The Huffington Post.
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- Italiano, Laura. (2012-05-14) So-called 'King of All Pimps' sentenced to four years in prison. New York Post. Webcache.googleusercontent.com. Retrieved on 2013-07-18.
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- "Perspective on Spitzer Sex Scandal". Larry King Live. CNN. March 13, 2008. Retrieved May 27, 2014.
- "Jason Itzler" at the Internet Movie Database