California billionaire Stephen Cloobeck has a penchant for controversy.
He was charged Tuesday with several felony counts related to his complicated Penthouse Pet girlfriend, who is facing a criminal trial in May, just weeks after he sheltered the disgraced Eric Swalwell.
The scandals came after he ran for California governor as the “Donald Trump of the Democrats,” before his campaign fizzled in November of last year. He then endorsed Swalwell before his campaign imploded.
But before all of that, he had to make money, and with the riches came controversy.
In 2021, Cloobeck was enveloped in a messy legal drama with his former girlfriend and OnlyFans model Stefanie Gurzanski.
He allegedly spent $1.3 million on lavish gifts and trips for her before learning she was secretly shooting content for OnlyFans.
He called himself “victim of a cunning serial fraudster” and sued her for a myriad of offenses, including fraud and trespassing.
“Little did I know when I turned my back,” he told Vanity Fair of the content, “she’s doing all these pictures every second of the day in my assets and putting them on the internet. I would have blown a gasket then if I knew that.”
She claimed his behavior was “erratic” and “disturbing” since they broke up.
He also claimed Gurzanski was “hardly works out” and made a crass comment about her sexual performance.
Then he became interested in 28-year-old Penthouse Pet Adva Lavie. Lavie had a reputation for allegedly fleecing rich men and was indicted in March.
She now faces several felony charges, but Cloobeck still wants to marry her. Any plans of a wedding outside California have been foiled as she is not permitted to leave the state with her ankle monitor.
Cloobeck’s upbringing enabled his political ambitions. He was born in California in 1961 and grew up in the San Fernando Valley.
His father was Sheldon Cloobeck, a real estate developer credited with being a key figure in the timeshare industry.
He never planned to follow in his father’s footsteps. Cloobeck planned to become a surgeon, graduating from Brandeis University in 1983 with a degree in psychobiology.
But he then changed path, choosing an education in pursuit of real estate. Cloobeck learned accounting at Cal State Northridge and then learned about business law at UCLA.
And at the young age of 29, he owned his first Las Vegas hotel. He would later found Diamond Resorts and star on “Undercover Boss.”
He sold his company in 2016 for $2.2 billion. The man described himself as a company fixer.
“I fixed the most broken of companies. Nobody could fix this company,” he told the SF Standard. “It’s in my first book. I’ll give you a copy.”
Before long, he wrapped himself in the Democratic machine to support his business ventures. He debated running for Nevada governor before former Democratic Sen. Harry Reid and former Democratic Nevada Gov. Steve Sisolak talked him out of it. Sisolak ran instead.
Cloobeck was so close to Reid, who served as Senate Majority Leader for eight years before his death in 2021, that he considered him a father figure and reportedly donated $1 million to rename Las Vegas’ largest airport after him.
Years later, he finally decided to become a cog in the machine himself.
He decided to run for California governor last year after he expressed dissatisfaction with every potential candidate, including former Vice President Kamala Harris.
“I interviewed every single candidate,” he said. “I interviewed everybody, and I said, ‘This is the best we got?’”
“I shouldn’t be here,” he said. “But those that are running for office right now, I would not trust with our life safety, I would not trust with our taxpayer dollars.”
Cloobeck deemed himself a conservative Democrat who would run as the “Donald Trump of Democrats,” bashing the president furiously and suing his enemies, much like how the president has done.
But his campaign fizzled, and never managed any particularly strong polling results. He dropped out of the race in November of last year and endorsed Swalwell. The billionaire expressed absolute confidence in the California Democrat then.
“So when Eric decided to do this, I realized he is absolutely the right person for the job, and the best thing I could do would be to step aside and support him 100%,” he said.
The two’s relationship soured in April after a myriad of sexual misconduct allegations plagued Swalwell and forced him out of Congress and the governor’s race. Swalwell has denied the allegations.
Swalwell had been sheltering in the billionaire’s mansion, but Cloobeck kicked him out after he filmed an apology video there.
He denounced the Democratic Party and became a Republican.
“I am no longer supporting Eric. F—ing tell everyone I’m a libertarian. F— you, Democrat Party. I’m a libertarian now,” Cloobeck told the Post.
The billionaire was arrested on Tuesday on several counts related to people in Lavie’s case. If convicted, he could face more than a decade in prison.
