SANTA ANA, Calif. – The man that a California sheriff says was most likely the "mastermind" of a daring escape from a maximum security jail last weekend racked up a stunning list of criminal exploits in the decade leading up to his breakout, including a high-speed police chase, a sordid torture case and a flight overseas to avoid capture.
But Hossein Nayeri also struggled with flashbacks after he was charged in a drunken driving accident that killed his high school best friend a decade ago and battled substance abuse and depression, according to court files. He was diagnosed and treated for bipolar disorder with episodes of mania and suffered his own injuries in the crash, the files show.
Orange County Sheriff Sandra Hutchens earlier this week cited Nayeri's troubled and conniving past when she labeled him as "most probably the mastermind" of a stunning jail break that blindsided authorities.
Nayeri, 37, and two other inmates, 43-year-old Bac Duong and 20-year-old Jonathan Tieu, sawed through a metal grate over a plumbing tunnel, then used a bedsheet to hoist themselves into a steam pipe and sliced through more metal and rebar to reach an unguarded section of roof. From there, they rappelled down four stories using a rope made of bed linens to reach freedom — the first jail break at the facility in nearly three decades, authorities said.
Nayeri's current attorney, Salvatore Ciulla, did not return a request for comment.
But for Nayeri, a former U.S. Marine, it wasn't the first — or the second or the third — flight from authorities.
In 2005, Nayeri was working as a manager at a paint store in Madera County when he was charged with vehicular manslaughter in the drunken driving death of what court files describe as his high school best friend. Nayeri lost control while driving back from a casino and the car rolled over and caught fire, said Steve Geringer, his defense attorney in that case.
While free on bail, Nayeri fled the state but was eventually recaptured in Washington and extradited to California in 2009.
At his sentencing, friends and family wrote letters to the judge on his behalf, saying that the accident had turned him into a shell of his former self. He hung a photo of his friend on the wall of his hospital room after the accident and cried daily, one friend wrote. His sister wrote that he stopped calling her and spent hours at his friend's gravesite.
Nayeri, who was burned over 15 percent of his body and lost toes in the wreck, told the judge he remembered the smell of burning flesh and was screaming his friend's name before he blacked out. He was trying to make amends by volunteering at the Red Cross and participating in Mothers Against Drunk Driving, he said.
"To this day I wish I wouldn't have gained consciousness to see the look on their faces," Nayeri wrote, according to the court file.
He was sentenced to less than a year in county jail and four years of probation, in part because of his lack of felony criminal history.
He was still on probation in 2012 when, prosecutors say, he fled during a traffic stop in Orange County and led police on a high-speed chase.
Nayeri managed to get away on foot after ditching the car, which was crammed with surveillance devices, video footage and GPS trackers.
About a week later, prosecutors say, Nayeri and three others kidnapped a medical marijuana distributor, bound him with zip ties and drove him to desert near Palm Springs where they believed he had buried a large sum of cash. There, the man was tortured with a blow torch and his penis severed as his girlfriend lay nearby, blindfolded, according to court files.
Police soon matched the ditched car to Nayeri and realized the surveillance gear inside had been used to monitor the victim, said Robert K. Weinberg, a defense attorney who is representing one of Nayeri's co-defendants in that case. As authorities closed in, Nayeri fled to Iran, where he was born.
He was arrested in 2013 in Prague as he tried to travel to Spain to meet his family. He was to go on trial Feb. 23 on charges that include kidnapping, torture and burglary.
Those whose lives intersected with Nayeri marvel at how quickly he went from a small-town paint store manager to one of the nation's most-wanted felons.
"He's clearly a really resourceful guy. Most people would kind of lay down in the mud and accept responsibility for what they did," said Roger Bonakdar, an attorney who represented the family of the classmate killed in the 2005 accident.
"I'm not sticking up for the guy by any means, but whatever the hell was going on with him, it really got out of control pretty quick."