Billionaire playboy’s scandal-clad rise to riches — after flop governor run as ‘Donald of the Democrats’



California billionaire Stephen Cloobeck has a penchant for controversy.

He was charged Tuesday with a number of felony counts associated to his sophisticated Penthouse Pet girlfriend, who’s dealing with a felony trial in Could, simply weeks after he sheltered the disgraced Eric Swalwell.

The scandals got here after he ran for California governor because the “Donald Trump of the Democrats,” earlier than his marketing campaign fizzled in November of final yr. He then endorsed Swalwell earlier than his marketing campaign imploded.

However earlier than all of that, he needed to make cash, and with the riches got here controversy.

Stephen Cloobeck attends an election night time watch social gathering on November 5, 2024 in Beverly Hills. Getty Photos
Cloobeck was charged with a number of felony counts associated to his sophisticated Penthouse Pet girlfriend, who’s dealing with a felony trial in Could. CA Publish

In 2021, Cloobeck was enveloped in a messy authorized drama along with his former girlfriend and OnlyFans mannequin  Stefanie Gurzanski.

He allegedly spent $1.3 million on lavish presents and journeys for her earlier than studying she was secretly capturing content material for OnlyFans.

He referred to as himself “sufferer of a crafty serial fraudster” and sued her for a myriad of offenses, together with fraud and trespassing.

“Little did I do know after I turned my again,” he advised Self-importance Truthful of the content material, “she’s doing all these footage each second of the day in my belongings and placing them on the web. I’d have blown a gasket then if I knew that.”

She claimed his conduct was “erratic” and “disturbing” since they broke up.

Adva Lavie, often known as Penthouse Pet, on the 2021 Maxim Halloween Celebration. Getty Photos

He additionally claimed Gurzanski was “hardly works out” and made a crass remark about her sexual efficiency.

Then he turned thinking about 28-year-old Penthouse Pet Adva Lavie. Lavie had a repute for allegedly fleecing wealthy males and was indicted in March.

She now faces a number of felony costs, however Cloobeck nonetheless needs to marry her. Any plans of a marriage outdoors California have been foiled as she will not be permitted to go away the state along with her ankle monitor.

Stephen Cloobeck and Barack Obama at a fundraiser on the Bellagio Lodge in Las Vegas on Oct. 24, 2011. AP

Cloobeck’s upbringing enabled his political ambitions. He was born in California in 1961 and grew up within the San Fernando Valley.

His father was Sheldon Cloobeck, an actual property developer credited with being a key determine within the timeshare business.

Cloobeck and his ex-wife Chantal in 1998. Getty Photos

He by no means deliberate to observe in his father’s footsteps. Cloobeck deliberate to turn out to be a surgeon, graduating from Brandeis College in 1983 with a level in psychobiology.

However he then modified path, selecting an training in pursuit of actual property. Cloobeck realized accounting at Cal State Northridge after which realized about enterprise legislation at UCLA.

And on the younger age of 29, he owned his first Las Vegas resort. He would later discovered Diamond Resorts and star on “Undercover Boss.”

Cloobeck on “Undercover Boss.” CBS by way of Getty Photos
Cloobeck with an worker on an episode of “Undercover Boss.” CBS by way of Getty Photos

He bought his firm in 2016 for $2.2 billion. The person described himself as an organization fixer.

“I fastened essentially the most damaged of corporations. No one might repair this firm,” he advised the SF Commonplace. “It’s in my first guide. I’ll provide you with a duplicate.”

Earlier than lengthy, he wrapped himself within the Democratic machine to help his enterprise ventures. He debated operating for Nevada governor earlier than former Democratic Sen. Harry Reid and former Democratic Nevada Gov. Steve Sisolak talked him out of it. Sisolak ran as an alternative.

Larry The Cable Man, left, skips down the 18th fairway with Stephen Cloobeck, proper, in the course of the Diamond Resorts Invitational at The Golden Bear Membership at Keene’s Level in Wintermere, Fla., on Jan. 16, 2016.
Tribune Information Service by way of Getty Photos

Cloobeck was so near Reid, who served as Senate Majority Chief for eight years earlier than his dying in 2021, that he thought-about him a father determine and reportedly donated $1 million to rename Las Vegas’ largest airport after him.

Years later, he lastly determined to turn out to be a cog within the machine himself.

He determined to run for California governor final yr after he expressed dissatisfaction with each potential candidate, together with former Vice President Kamala Harris.

“I interviewed each single candidate,” he mentioned. “I interviewed all people, and I mentioned, ‘That is the most effective we received?’”

“I shouldn’t be right here,” he mentioned. “However these which might be operating for workplace proper now, I’d not belief with our life security, I’d not belief with our taxpayer {dollars}.”

Cloobeck deemed himself a conservative Democrat who would run because the “Donald Trump of Democrats,” bashing the president furiously and suing his enemies, very like how the president has performed.

However his marketing campaign fizzled, and by no means managed any notably sturdy polling outcomes. He dropped out of the race in November of final yr and endorsed Swalwell. The billionaire expressed absolute confidence within the California Democrat then.

Stephen Cloobeck speaks to Fox Information outdoors his mansion in Beverly Hills, April 13, 2026. David Buchan for CA Publish

“So when Eric determined to do that, I spotted he’s completely the suitable particular person for the job, and the most effective factor I might do can be to step apart and help him 100%,” he mentioned.

The 2’s relationship soured in April after a myriad of sexual misconduct allegations plagued Swalwell and compelled him out of Congress and the governor’s race. Swalwell has denied the allegations.

Swalwell had been sheltering within the billionaire’s mansion, however Cloobeck kicked him out after he filmed an apology video there.

He denounced the Democratic Celebration and have become a Republican.

“I’m not supporting Eric. F—ing inform everybody I’m a libertarian. F— you, Democrat Celebration. I’m a libertarian now,” Cloobeck advised the Publish. 

The billionaire was arrested on Tuesday on a number of counts associated to folks in Lavie’s case. If convicted, he might face greater than a decade in jail.



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