He was born into a life of unimaginable wealth and privilege, once describing himself as "without doubt, the luckiest guy around".
But according to friends of billionaire James Packer, it was a gift that came with enormous pressure to succeed, costing him his marriages and affecting his mental health.
Packer, his mates say, was determined to cast off the shadow of his late father Kerry and build his own empire.
Former Labor powerbroker Graham Richardson, one of Kerry Packer's closest friends, told A Current Affair: "I think he was always trying to be Kerry and he shouldn't have been, because he's not Kerry.
"I think that by doing so he placed way too much pressure on himself and it came down to how much money he was worth."
Richardson said Kerry Packer was relentlessly tough on his only son, describing James as "a very, very bright guy".
"You couldn't characterise it as your average father-son relationship, there was nothing like it," he told ACA.
"So Kerry, I think, was too hard on (James) at times," he said.
"And being tough physically was very important to the Packers, quite apart from being tough mentally."
Richardson told ACA he saw Kerry Packer "be pretty hard on James in front of others".
"He chose quite often to do it in front of others. I saw it myself three or four times, which wasn't overly pleasant."
News Corp journalist Damon Kitney, the author of The Price of Fortune – The Untold Story of Being James Packer, told ACA James believed his father did not realise the impact he was having on his son.
"I do think there were probably times in James's life when Kerry was too hard on James," he told ACA.
"But I think sometimes – and James makes this point himself – Kerry probably didn't realise the impact he was having on his son."
After the shocking 2001 collapse of OneTel, the telecommunications company that Packer had backed, the billionaire spent a lot of time in the US.
He became involved in Scientology and developed a close friendship with Tom Cruise.
More recently, Packer became particularly close to Hollywood legend Warren Beatty.
Beatty acted as a mentor to the troubled Packer, letting him live in the guesthouse of his sprawling Hollywood compound.
"I think the most important thing Warren did for James, and it's documented amazingly, is that he drove him to psychiatrist offices in LA when James was at his lowest point, when he was really hitting the booze hard," Kitney told ACA.
Ironically, it was the big-budget flop of Beatty's film Rules Don't Apply that prompted Packer to pull his money from the production company RatPac, which he had formed with director Brett Ratner.
William D. Cohen, a special correspondent for Vanity Fair, said the collapse of RatPac was a case of "dumb money".
"In Hollywood, unfortunately, there's this whole idea of 'dumb money'. People with a lot of money decide they're going to come to Hollywood, invest in movies, be part of the fast crowd in Hollywood, hang out with movie stars and inevitably the smart money takes the dumb money."
Cohen was equally scathing when it came to Packer's former fiancee, Mariah Carey.
"She's a very difficult personality," he told ACA. "She's a notorious diva, she's very hard on the people who work for her."
Packer and Carey became engaged, but James's friend Kerry Stokes has admitted he thought the relationship was not what James needed and decided to intervene.
Stokes, the owner of Seven West Media, sent Packer to Israel to give him some space from the ongoing drama, leading to the end of the billionare's relationship with the singer.
Despite Packer's resignation from the board of Crown Resorts earlier this year, Kitney told ACA the billionaire was now in "a much better place" mentally.