A business manager who stole more than seven million dollars (£5.4m) from Alanis Morissette and others has been jailed for six years after the singer made a pitch for a lengthy and severe sentence saying he stole her dreams.
Morissette said she had placed the fortune she earned through her fame in the trust of Jonathan Schwartz and he had secretly siphoned her accounts while constantly misleading her about her net worth.
"He did this in a long, systematic, drawn-out and sinister manner" that would have bankrupted her within three years had the thefts continued, she said.
Schwartz, 47, who blamed his gambling addiction for the thefts, wept and apologised at the hearing in Los Angeles, saying he took full responsibility for his behaviour and would have a life of shame because of it.
"I alone am responsible for the devastation," he said. "I will spend the rest of my life asking for forgiveness."
Prosecutors were seeking just over five years in prison for Schwartz, but Judge Dolly Gee said she thought he deserved more time for the "sheer audaciousness of this conduct".
She noted that she had often criticised federal sentencing guidelines as draconian, but noted that they were not harsh enough in this case.
Judge Gee said Schwartz's gambling addiction may explain the wire fraud and tax crimes, but did not excuse them. She also ordered him to pay 8.6 million dollars in restitution.
Schwartz acknowledged stealing nearly five million dollars from Morissette between May 2010 and January 2014 and more than two million from five unnamed clients when he worked at GSO Business Management, a firm that touted relationships with entertainers such as Katy Perry, 50 Cent and Tom Petty.
Schwartz was a high-flying partner making 1.2 million dollars a year, according to court papers.
The thefts struck a blow to the firm's reputation that is expected to cost 20 million dollars and led to nearly a dozen job losses, according to founder Bernard Gudvi.
The embezzlement was discovered by a new money manager Morissette hired.
"It was at this time, I realised he also stole my dreams," she said.
When the firm was contacted about the apparent theft, Schwartz made "wild accusations" that his former client was in the throes of drug addiction and mentally unstable, Mr Gudvi said.
Schwartz also falsely claimed Morissette invested the money in an illegal marijuana growing business.
"As the walls were closing in on the scheme to steal client funds ... he was unable to turn away from the lies," Mr Gudvi said in a letter to the court.
"The worse things became, the more easily he seemed to dispense with the truth."
Prosecutors acknowledged that Schwartz lost some money gambling, but said the funds financed a lavish lifestyle.
"Every expression of remorse he has made and every purported act of self-improvement he has taken occurred only after he realized he had no 'choice' to do otherwise," assistant US attorney Ranee Katzenstein said in court papers.
Schwartz, who was sacked, had offered financial guidance to some of the biggest stars and was said to represent Beyonce and Mariah Carey, who both appeared at a fund-raiser last year in support of a heart disease charity he founded.
He penned a mea culpa in The Hollywood Reporter last month, saying his father was a gambling addict who abandoned his family and he sought refuge in sports betting and drugs to deal with the stress from his business.
"The spiral I was in was toxic," Schwartz wrote.
"Winning did not make me feel better but losing was intolerable.
"If I lost, then I had to make it back and when I lost again, the hole I had dug got deeper and deeper.
"I felt weak and powerless, terrified by my internal demons that I was turning into my father."