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Conrad Hilton

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Conrad Hilton is headed to prison.

On Monday, U.S. Magistrate Judge Suzanne H. Segal revoked probation for the 22-year-old hotel heir. Conrad was sentenced to spend two months in prison after he failed several drug tests and was removed from a court-ordered residential substance abuse treatment program. According to the courts, Conrad tested positive for drugs—including cocaine, marijuana and synthetic cannabinoids—three times within a year, violating the terms of his probation stemming from an outburst on an international flight in 2014. His attorney, Robert Shapiro, persuaded the judge to allow his client to self-surrender to federal authorities within 48 hours.

During the hearing, assistant U.S. attorney Alexander Schwab said Conrad was given multiple chances to obey the terms of his probation. "What we haven't tried yet is a custodial term," he said, noting that Conrad has reoffended "in precisely the same way—over and over and over."

Conrad, whose parents joined him court, asked the judge to let him serve the 60-day sentence under house arrest at his grandfather's home in Palm Springs; he said it would be easier to avoid his friends in L.A. who are "a bad influence." As for Rick Hilton and Kathy Hilton's home? Conrad said it's a "bad environment" where he's "used to just sitting there and getting high 24-7." He also asked to do a "work program" instead of doing hard time; that request was denied. Robert made a bid to have the judge lower the jail sentence to 30 days, but she rejected the idea. Suzanne warned Conrad that he must stay sober before turning himself in by Wednesday.

In 2015, Conrad pleaded guilty to attacking several flight attendants during a British Airways flight from London to L.A. A judge placed him on three years probation and ordered him to complete 750 hours of community service. During that nearly 11-hour trip, Conrad physically threatened two crewmembers and repeatedly smoked marijuana and cigarettes in the airplane lavatory, according to the U.S. Attorney's Office. He also referred to his fellow passengers "peasants" and accused flight attendants of "taking the peasants' side." He was later restrained and handcuffed. "I could get you all fired in five minutes. I know your boss," he told them, per the complaint. "My father will pay this out; he has done it before. Dad paid $300,000 last time."

Six days after pleading guilty to the charges, Conrad was arrested again for allegedly violating a restraining order by visiting his ex-girlfriend's Hollywood Hills home.

In a separate court case in May, Conrad pleaded guilty to a charge of evading arrest. He was sentenced to 90 days in sheriff's custody, with 89 days in the work release program, and was also given three years probation. Conrad had been charged with one felony count of reckless evading of a peace officer, stemming from a 2014 incident in which he fled from a California Department of Fish and Game officer who pulled him over for speeding. Conrad pleaded not guilty to the charge in September, but withdrew the plea during a felony settlement conference.