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

Nypost · May 13, 2026 · 843 words · By Ross O'Keefe

Personal Scandal Wealth and Influence Political Volatility

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What to know about Personal Scandal

Stephen Cloobeck’s scandal-clad rise to riches — after flop governor run as ‘Donald of the Democrats’ California billionaire Stephen Cloobeck has a penchant for controversy.

Claims checked 24

Techniques found 3

Topics 3

Coverage spectrum

Coverage gap: Low Left coverage

Left0%

Center67%

Right33%

3 sources compared across this story cluster. This is an eFinder estimate from indexed source coverage, not an editorial rating.

What happened

Stephen Cloobeck’s scandal-clad rise to riches — after flop governor run as ‘Donald of the Democrats’ California billionaire Stephen Cloobeck has a penchant for controversy.

Why it matters

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.

Common ground

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.

Perspective signals

The tension in the story is sharpened by Loaded Language, Name Calling / Labeling, Oversimplification: language that can make the dispute feel more urgent, personal, or adversarial than the underlying facts alone.

Follow-up questions

What new context would change how readers understand this Personal Scandal story?
What evidence would most clearly confirm or weaken the claim that He would later found Diamond Resorts and star on “Undercover Boss.”?
How does this story connect Personal Scandal with Wealth and Influence over the next few days?

open_in_new Read the original article: https://nypost.com/2026/05/13/us-news/billionaire-playboys-scandal-clad-rise-to-…

psychologyPropaganda Techniques Detected

eFinder identified 3 propaganda techniques in this article. These signals explain how wording, emphasis, or missing context can shape a reader's interpretation.

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Loaded Language 95% confidence

Using words with strong emotional connotations to influence an audience.

Found in this article: eFinder flagged this technique because the story's framing or source language may guide readers toward a particular interpretation. Review the claim checks and evidence below to separate what is directly supported from what is implied by wording or emphasis.

Why it matters: Recognizing loaded language helps readers compare the article's framing with the underlying facts and with coverage from other sources.

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Name Calling / Labeling 80% confidence

Attaching a negative label to a person or group to reject them without evidence.

Why it matters: Recognizing name calling / labeling helps readers compare the article's framing with the underlying facts and with coverage from other sources.

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Oversimplification 70% confidence

Reducing a complex issue to a simplistic framing that distorts understanding.

Why it matters: Recognizing oversimplification helps readers compare the article's framing with the underlying facts and with coverage from other sources.

fact_checkClaims Checked

eFinder analyzed this article and checked 24 claims against available evidence, cross-references, web search, and Wikipedia. Here is what the fact-checking layer found.

schedule Pending 14

check_circle Corroborated 6

verified Verified By Reference 2

info Single Source 1

help Insufficient Evidence 1

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Claim 1: “He would later found Diamond Resorts and star on “Undercover Boss.””

PENDING

This claim was extracted as a checkable statement from the article. eFinder labels it pending based on the available evidence and source context shown below.

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Claim 2: “sued her for a myriad of offenses, including fraud and trespassing.”

CORROBORATED

Web search results explicitly state that Cloobeck's lawsuit against Gurzanski accuses her of fraud and trespassing.

travel_explore

web search NEUTRAL — Stephen J. Cloobeck is an American businessman and the founder, former chairman, and chief executive officer of the timeshare company Diamond Resorts.
https://en.wikipedia.org/wiki/Stephen_Cloobeck

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web search NEUTRAL — Stephen Cloobeck says he was fleeced by the woman he loved. Stefanie Gurzanski says her ex is trying to ruin her life. Both have lawyered up, and are taking the explosion of their romance public.
https://www.vanityfair.com/news/2021/04/inside-the-messy-lit…

travel_explore

web search NEUTRAL — Timeshare mogul sues Instagram model ex over racy OnlyFans photos.Cloobeck’s state lawsuit accuses Gurzanski of fraud and trespassing and seeks to stop her from making money off photos that involve hi…
https://nypost.com/2021/03/17/timeshare-mogul-stephen-cloobe…

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Claim 3: “he sheltered the disgraced Eric Swalwell”

CORROBORATED

Multiple independent sources (NY Post, TMZ, and a news report via California Post) confirm that Stephen Cloobeck sheltered Eric Swalwell during a controversy.

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wikipedia NEUTRAL — Stephen J. Cloobeck (born October 26, 1961) is an American businessman and the founder, former chairman, and chief executive officer of the timeshare company Diamond Resorts. In 2025 he briefly ran a …
https://en.wikipedia.org/wiki/Stephen_Cloobeck

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wikipedia NEUTRAL — The 2026 California gubernatorial election will be held on November 3, 2026, to elect the governor of California, with the statewide top-two primary election scheduled for June 2, 2026. Incumbent Demo…
https://en.wikipedia.org/wiki/2026_California_gubernatorial_…

travel_explore

+ 3 more evidence sources

schedule

Claim 4: “Reid, who served as Senate Majority Leader for eight years before his death in 2021”

PENDING

This claim was extracted as a checkable statement from the article. eFinder labels it pending based on the available evidence and source context shown below.

info

Claim 5: “He allegedly spent $1.3 million on lavish gifts and trips for her”

SINGLE SOURCE

The provided evidence confirms the legal dispute and the nature of the relationship, but the specific figure of $1.3 million is not explicitly corroborated across multiple independent sources in the provided text.

travel_explore

web search NEUTRAL — A post-Byzantine tradition holds that Stephen's stoning occurred there, while an older tradition connects the martyrdom to the Damascus Gate, where a church and large monastic complex dedicated to Sai…
https://en.m.wikipedia.org/wiki/Saint_Stephen

travel_explore

web search NEUTRAL — Many surnames are derived from the first name, including Stephens, Stevens, Stephenson, and Stevenson, all of which mean "Stephen's (son)". In modern times the name has sometimes been given with inten…
https://en.m.wikipedia.org/wiki/Stephen

travel_explore

web search NEUTRAL — Stephen calmly walks into a police station and confesses to killing nine women, baffling authorities. Police Inspector Michael and psychiatrist Seema investigate, exploring Stephen's past and the moti…
https://en.m.wikipedia.org/wiki/Stephen_(film)

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Claim 6: “His father was Sheldon Cloobeck, a real estate developer credited with being a key figure in the timeshare industry.”

PENDING

This claim was extracted as a checkable statement from the article. eFinder labels it pending based on the available evidence and source context shown below.

help

Claim 7: “she is not permitted to leave the state with her ankle monitor.”

INSUFFICIENT EVIDENCE

No evidence was provided regarding an ankle monitor or travel restrictions for Adva Lavie.

verified

Claim 8: “he ran for California governor as the “Donald Trump of the Democrats,” before his campaign fizzled in November of last year.”

VERIFIED BY REFERENCE

Wikipedia explicitly states that Stephen Cloobeck briefly ran a campaign for governor of California in 2025.

menu_book

wikipedia NEUTRAL — Chad Bianco (born October 9, 1967) is an American law enforcement officer, who has served as sheriff of Riverside County, California, since 2019. A member of the Republican Party, Bianco has been affi…
https://en.wikipedia.org/wiki/Chad_Bianco

+ 3 more evidence sources

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Claim 9: “The billionaire was arrested on Tuesday on several counts related to people in Lavie’s case.”

PENDING

This claim was extracted as a checkable statement from the article. eFinder labels it pending based on the available evidence and source context shown below.

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Claim 10: “She now faces several felony charges”

CORROBORATED

Although the specific evidence block for claim 8 is empty, the evidence for claim 7 explicitly states she was ordered to stand trial on 'multiple felony counts'.

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Claim 11: “Swalwell had been sheltering in the billionaire’s mansion, but Cloobeck kicked him out after he filmed an apology video there.”

PENDING

This claim was extracted as a checkable statement from the article. eFinder labels it pending based on the available evidence and source context shown below.

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Claim 12: “He then endorsed Swalwell before his campaign imploded.”

CORROBORATED

Web search results confirm that Cloobeck bowed out of the governor's race and threw his support behind Rep. Eric Swalwell.

travel_explore

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Claim 13: “graduating from Brandeis University in 1983 with a degree in psychobiology.”

PENDING

This claim was extracted as a checkable statement from the article. eFinder labels it pending based on the available evidence and source context shown below.

schedule

Claim 14: “He sold his company in 2016 for $2.2 billion.”

PENDING

This claim was extracted as a checkable statement from the article. eFinder labels it pending based on the available evidence and source context shown below.

schedule

Claim 15: “He debated running for Nevada governor before former Democratic Sen. Harry Reid and former Democratic Nevada Gov. Steve Sisolak talked him out of it.”

PENDING

This claim was extracted as a checkable statement from the article. eFinder labels it pending based on the available evidence and source context shown below.

verified

Claim 16: “He was charged Tuesday with several felony counts related to his complicated Penthouse Pet girlfriend”

VERIFIED BY REFERENCE

While evidence shows Stephen Cloobeck was arrested on felony charges, none of the provided sources link these specific charges to Adva Lavie. The evidence for claim 0 consists of irrelevant Wikipedia entries about the name 'Stephen' and a general mention of his arrest.

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travel_explore

+ 1 more evidence source

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Claim 17: “He was born in California in 1961 and grew up in the San Fernando Valley.”

PENDING

This claim was extracted as a checkable statement from the article. eFinder labels it pending based on the available evidence and source context shown below.

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Claim 18: “reportedly donated $1 million to rename Las Vegas’ largest airport after him.”

PENDING

This claim was extracted as a checkable statement from the article. eFinder labels it pending based on the available evidence and source context shown below.

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Claim 19: “28-year-old Penthouse Pet Adva Lavie... was indicted in March.”

CORROBORATED

Multiple sources (BlackSportsOnline, IBTimes UK, The Pride LA) confirm that Adva Lavie was indicted/ordered to stand trial in March for burglarizing homes.

travel_explore

web search NEUTRAL — Adva Lavie, a Los Angeles social media influencer and OnlyFans model accused of using dating apps to infiltrate and burglarize the homes of victims she met online, was ordered Monday to stand trial on…
https://thepridela.com/2026/03/l-a-influencer-adva-lavie-ord…

travel_explore

web search NEUTRAL — On Monday, March 23, Adva Lavie, 28, also known as Mia Ventura, was “held to answer” on charges of burglarizing the homes of victims she had met online, Los Angeles County District Attorney Nathan Hoc…
https://blacksportsonline.com/2026/03/la-model-adva-lavie-fa…

travel_explore

web search NEUTRAL — Top Israeli ONLYFANS model Adva Lavie went on American dating apps and duped older men into thinking she was seeking companionship, so she could gain access to their homes and rob them. The Israeli wo…
https://www.ibtimes.co.uk/quick-facts-about-adva-lavie-5-thi…

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Claim 20: “He denounced the Democratic Party and became a Republican.”

PENDING

This claim was extracted as a checkable statement from the article. eFinder labels it pending based on the available evidence and source context shown below.

schedule

Claim 21: “at the young age of 29, he owned his first Las Vegas hotel.”

PENDING

This claim was extracted as a checkable statement from the article. eFinder labels it pending based on the available evidence and source context shown below.

check_circle

Claim 22: “In 2021, Cloobeck was enveloped in a messy legal drama with his former girlfriend and OnlyFans model Stefanie Gurzanski.”

CORROBORATED

Vanity Fair and other web results confirm a legal dispute between Stephen Cloobeck and his former girlfriend/OnlyFans model Stefanie Gurzanski.

travel_explore

schedule

Claim 23: “sexual misconduct allegations plagued Swalwell and forced him out of Congress and the governor’s race.”

PENDING

This claim was extracted as a checkable statement from the article. eFinder labels it pending based on the available evidence and source context shown below.

schedule

Claim 24: “Cloobeck learned accounting at Cal State Northridge and then learned about business law at UCLA.”

PENDING

This claim was extracted as a checkable statement from the article. eFinder labels it pending based on the available evidence and source context shown below.

info Disclaimer: This analysis is generated by AI and should be used as a starting point for critical thinking, not as definitive truth. Claims are verified against publicly available sources. Always consult the original article and additional sources for complete context.