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Bruno Perillo was born into privilege - a world of private schooling, holidays at the beach houses of rich listers and wealthy parents with a success-ful business.
Later in life he would rub shoulders with Auckland's rich and famous - sitting at a table at Fight for Life with Mike King and property tycoon Pat Rippin, who befriended the friendly newcomer. He would drink champagne at the home of celebrity Charlotte Dawson. What Perillo, 35, lacked in height, he made up with charm and personality. "He oozed with personality and everyone loved Bruno," a close friend remembers.
Former friends and associates could scarcely believe it was the same person when they saw newspaper photos of Perillo looking prematurely aged and gaunt, after he was arrested for his alleged involvement in a hostage drama.
Perillo is in Mt Eden Prison's remand wing, facing 12 charges - including three of kidnapping - after he allegedly took a trio of panelbeaters hostage at a West Auckland warehouse two weeks ago. It is alleged that after he fled from police in a dangerous, high-speed car chase he spent three hours holed up at a New Lynn garage with the terrified hostages held at gunpoint. The Hollywood flick-style chaos caused major disruption to much of West Auckland and ended with a man - alleged to be Perillo - being forced to leave the building after armed police threw grenades. When Perillo appeared in court last week he was remanded so further psychiatric assessments could be carried out.
Bruno Perillo grew up with his three brothers, Gino, now 44, Dario, 42, and Rico, 39, in Glendowie with their parents Ron and Wendy. Ron Perillo was one of the four Perillo brothers who launched Andrea Biani footwear in the 1960s, a brand which became one of New Zealand's most successful. The boys went to Sacred Heart College, rubbing shoulders with the sons of some of Auckland's wealthiest families. Bruno Perillo enjoyed weekends and holidays at the beach houses of friends like the Giltraps. In winter they holidayed in Fiji.
Former friends remembered being envious of the older Perillo boys' lifestyle. "In the 80s they were the most desired boys in town and had sports cars to burn," one said. "They had a beautiful house and beautiful friends - anyone who is on the rich list now were their friends then."
In 1985 Ron and Wendy Perillo took their sons to the Gold Coast to expand their extended footwear empire. Four years later, Ron and Wendy Perillo were seriously injured when their Porsche and a bus collided.
After leaving college, Bruno Perillo became a cabinet maker but by 2004 was back and keen to infiltrate Auckland's glitterati. He made friends with the right people, worked his way into Auckland's hippest scene and had his photo in social pages.
Dario Perillo said he thought his brother's involvement in Auckland's social scene contributed to his downfall. "He loved it, he thought it was great. I think he had too much of the good life and [it] was doing what the celebrities were doing that caused him to become unstuck."
A former childhood friend, who has asked not to be named for fear of his safety, remembers Perillo returning to New Zealand with stories of how he had been friends on the Gold Coast with American heiress Paris Hilton, a bond he claimed he formed while she was there filming House of Wax.
"He actually handed the phone over to me and told me to say hello to Paris. It sounded like her and I got off the phone believing I had spoken with Paris."
Dario Perillo, who lives in Kumeu, is angry that social services did not help his brother sooner and says mental health agencies have "blood on their hands". He told the Herald on Sunday that he refuses to watch his brother go to jail.
"This is not his fault, he needed help and he didn't get it. I am not going to see anything happen to him."
The Paris Hilton interview that never happened
The Edge radio station thought they had a New Zealand exclusive - an interview with Paris Hilton. They were so confident they gave a hat, autographed by Tom Cruise and meant to be sold for charity, to Auckland man-about-town Bruno Perillo who convinced them he would arrange the interview. But it was a con. There was no link between Perillo and Hilton.
The Edge breakfast co-announcer, Jay Jay Feeney, told the Herald on Sunday she was conned into believing that Perillo and Hilton were best buddies. She remembers being introduced to Perillo in 2004 by a well-known Auckland newspaper columnist.
"Everyone was talking him up and so I thought he was for real."
Perillo came into the radio station and convinced Feeney he knew Hilton and said he had been out on a boat with her and that he was bringing her to New Zealand.
Feeney and her husband, co-host Dom Harvey, pursued Perillo in the hope he could introduce them to Hilton and help arrange an interview on their breakfast show. The tall tale was made more believable because Perillo had just returned from Australia where Hilton was filming House of Wax.
Perillo took a fancy to a hat autographed by movie star Tom Cruise, which was supposed to be auctioned off at a children's charity function that Christmas. The hat was expected to raise $1000. "He asked if he could have the cap, he really wanted it," Feeney said. She said Perillo became obsessed with her and began ringing constantly and at odd hours.
"He was getting quite full on and wasn't delivering on what he was promising to us".
When the Herald on Sunday called Feeney last week she laughed when she realised the person who had led her to believe she could score a chat with Hilton was in fact Perillo - the man who faces multiple charges for bringing West Auckland to a stand-still in a blockbuster-style hostage drama on July 10.
"I didn't recognise him at first and then I thought 'Oh my God, that was the guy who was ringing me in the middle of the night trying to get me to go out with him'."