"I kind of looked in the mirror all the time and saw this ugly kid, or like I wasn't good enough and I would always get really down on myself," Prugo said.
Struggling, Prugo transferred to an alternative school, Indian Hills High in Agoura Hills, Calif. There he met Rachel Lee, who he said would change his life.
"She was always really nice to me, always kind of took me under her wing," Prugo said.
Lee was everything Prugo wasn't. She was upper-class, popular, the consummate "it" girl who would bring Prugo into the Calabasas inner circle and introduce him to the vibrant L.A. party scene.
She also had a history of trouble with the law and was on probation for petty theft. "Their relationship is very interesting," said Nancy Jo Sales, a writer who profiled the alleged burglars for Vanity Fair. "She was this very powerful girl, who is popular and has this kind of wild streak. He, on the other hand, is this very timid, searching kind of personality. He's friendless and they get together and trouble ensues."
Prugo got to know Lee's friends.
"She introduced me to her friends and they were all pretty and like her and we clicked," said Prugo. "I'm hanging out with all these pretty women and, you know, [it] made me feel good."
His new social network included a teen named Courtney Ames and reality star hopefuls Alexis and Gabby Neiers. Prugo was suddenly thrust into the L.A. nightlife. He started doing drugs, he said.
"I started stealing from my parents for money for these drugs," Prugo said.
Prugo says he suddenly found himself in a daze of boozy, coke-induced all-nighters.
But the real drug of choice for Prugo and some of his friends was celebrity: knowing, hanging around and looking like celebrities.
Prugo said nobody wanted a piece of the celebrity world more than Lee.
The friend obsessively watched reality TV and entertainment programs to see what the bold-face names were wearing, Prugo said. For most teens, that's where it may end, but Prugo says, for Lee and him, it was just the beginning. According to Prugo, the two started to steal luxury items and wallets from unlocked cars at night.
"We'd go around opening cars and finding, like, purses and wallets and that would be easy money," said Prugo.
From there, it escalated, Prugo said. He says they decided they needed to have exactly what the celebrities owned and wore.
"It escalated into our first house," he said.
And it was not just any house: He says the pair decided to burglarize the home of Paris Hilton.
"Rachel called it going shopping," Prugo said.
Prugo said the friends told themselves of their targets, "They are celebrities, they have everything."
Prugo said he and Lee used Facebook and Twitter to track celebrities' movements and used Google Earth to scope out their homes.
"Well, you'd check online to kind of make sure they weren't around," said Prugo. "I mean, these people are constantly shooting movies or they are constantly working."
Prugo and Lee drove to Hilton's gated community at 2 a.m., he said. Prugo says they had noticed a way into the community on Google Earth, and they climbed a hill and arrived at Hilton's front door.
"We'd first ring the doorbell," Prugo said, to see if anyone was home. "Rachel and I looked under the mat, found a key." No key was needed though, Prugo said: Hilton's house was unlocked.