Stephen Cloobeck stands as one of America’s most successful businessmen, with an estimated net worth of $500 million. The Diamond Resorts International founder built his empire through strategic investments in the timeshare industry, eventually selling his company for $2.2 billion in a landmark deal with Apollo Global Management acquisition.
Born on October 26, 1961, this Nevada businessman biography showcases a remarkable journey from aspiring surgeon to timeshare industry mogul. His appearance on Undercover Boss Stephen Cloobeck episode brought him widespread recognition, while his recent announcement as a California governor candidate 2026 marks an exciting new chapter in his already impressive career.
Stephen Cloobeck Net Worth Forbes & Billionaire Status
What is Stephen Cloobeck’s Net Worth?
The net worth of Stephen Cloobeck officially stands at $500 million, primarily earned from the Diamond Resorts sale value in 2016. As a Brandeis University alumni, he transformed a single hotel project into a global hospitality empire spanning 370 resorts across 35 countries worldwide.
His Stephen Cloobeck fortune came from owning approximately 22% of Diamond Resorts at the time of sale. The Apollo Global Management acquisition delivered him a massive pre-tax windfall, establishing him as one of the wealthiest figures in the travel and hospitality sector.
Key Financial Milestones:
- Diamond Resorts sale: $2.2 billion (2016)
- Personal payout: $500 million pre-tax
- Equity stake: 22% ownership
- Current estimated wealth: $500 million
| Asset Category | Estimated Value | Details |
| Diamond Resorts Sale | $500 million | 22% equity stake (2016) |
| Beverly Hills Mansion | $100 million | “Papillon” estate |
| Cabo San Lucas Home | $45 million | Luxury beachfront property |
| Real Estate Portfolio | $185+ million | Multiple luxury properties |
Stephen Cloobeck Billionaire Claim
The Stephen Cloobeck billionaire claim remains a topic of debate and intrigue. In various interviews, the American entrepreneur profiles feature him stating he achieved billionaire status, though official documentation hasn’t confirmed this assertion through public financial disclosures or verified sources.
His luxury real estate portfolio includes the Beverly Hills mansion Papillon valued at $100 million and a Cabo San Lucas luxury home worth $45 million. Combined with undisclosed investments and assets, the Stephen Cloobeck billionaire claim could potentially be accurate, especially considering pre-divorce holdings.
Wealth Indicators:
- Claims billionaire status publicly
- Owns properties worth $145+ million
- Two expensive divorce settlements
- Undisclosed investment portfolio
Early Life and Career Beginnings
Stephen Cloobeck’s Childhood & Education
Stephen Cloobeck biography begins on October 26, 1961, making Stephen Cloobeck age 63 in 2025. The Stephen Cloobeck early life included attending Brandeis University, where he graduated in 1983 with a degree in Psychobiology, initially planning medical or legal careers.
Stephen Cloobeck education prepared him for medicine and law, gaining acceptance to both medical and law schools. However, the Stephen Cloobeck entrepreneur journey took an unexpected turn toward real estate development, ultimately leading to his extraordinary success in business.
Educational Background:
- Born: October 26, 1961
- University: Brandeis University
- Degree: Psychobiology (1983)
- Original career plans: Surgeon or lawyer
Early Business Ventures
Stephen Cloobeck career initially focused on developing shopping centers throughout Southern California. His first project in Burbank launched a series of successful developments across multiple SoCal cities, demonstrating his natural talent for identifying profitable real estate opportunities and executing complex projects.
The travel industry business leader then pivoted to Las Vegas hospitality. In 1991, he began constructing the Polo Towers hotel, which opened in 1992 as a 21-story establishment on the Strip, marking his entry into the industry that would define his legacy.
| Year | Business Venture | Location | Outcome |
| 1983-1990 | Shopping Centers | Southern California | Multiple successful projects |
| 1991 | Polo Towers Construction | Las Vegas Strip | 21-story hotel |
| 1992 | Diamond Resorts Founded | Las Vegas | Industry transformation |
Early Career Highlights:
- Built shopping centers in 6+ SoCal cities
- Transitioned from retail to hospitality
- Opened Polo Towers in Las Vegas (1992)
- Founded Diamond Resorts same year
Rise of Diamond Resorts International
Founding of the Company
The Diamond Resorts founder established Diamond Resorts International in 1992, revolutionizing the timeshare industry with innovative vacation ownership models. His vision transformed how Americans approached vacation planning, creating accessible luxury experiences for middle-class families seeking memorable getaways.
Stephen Cloobeck businessman strategies focused on acquiring underperforming properties and transforming them into premier destinations. This approach allowed rapid expansion while maintaining quality standards, establishing Diamond Resorts as a trusted name in vacation ownership across multiple continents.
Company Foundation Details:
- Founded: 1992
- Initial focus: Timeshare innovation
- Business model: Vacation ownership
- Geographic start: Las Vegas, Nevada
Growth, Expansion & $2.2 Billion Sale
Diamond Resorts International CEO Stephen Cloobeck expanded operations to 370+ resorts across 35 countries. The Sunterra Corporation acquisition in 2007 marked a significant milestone, strengthening the company’s market position and customer base with over 400,000 annual vacationers utilizing properties.
In June 2016, corporate acquisitions in hospitality reached a peak when Apollo Global Management purchased Diamond Resorts for $2.2 billion, a 26% premium over closing price. This luxury hotel and resort development deal netted Cloobeck $500 million, cementing his status among America’s wealthiest entrepreneurs.
| Milestone | Year | Impact |
| Company Founded | 1992 | Timeshare revolution begins |
| Sunterra Acquisition | 2007 | Major expansion |
| Apollo Sale | 2016 | $2.2 billion exit |
| Hilton Ownership | Current | Continued operations |
Expansion Timeline:
- 370+ resorts worldwide
- Operations in 35 countries
- 400,000+ annual customers
- Acquired by Hilton (post-Apollo)
Stephen Cloobeck on Undercover Boss
Episodes and Public Recognition
The Undercover Boss Stephen Cloobeck episode premiered in January 2012 during season 3, spanning episodes 1 and 2. His appearance showcased authentic leadership style and genuine concern for employees, resonating deeply with viewers and establishing him as an empathetic business philanthropy in America advocate.
Stephen Cloobeck profile gained mainstream recognition through the reality series. His emotional connection with workers and immediate action to improve their situations demonstrated CEO leadership spotlight qualities, making episodes among the series’ most memorable and frequently referenced by fans.
Television Appearances:
- First appearance: January 2012
- Season 3, Episodes 1-2
- Multiple subsequent appearances
- Highly rated episodes
Impact on His Career
The show amplified Stephen Cloobeck net worth 2025 discussion and public interest in his business practices. His authentic portrayal as a caring employer enhanced Diamond Resorts’ reputation, directly contributing to employee morale, customer loyalty, and ultimately increasing company valuation before the eventual sale.
National tourism organization leadership roles expanded following his television success. The positive exposure strengthened his credibility as a hospitality industry thought leader, opening doors to board positions and speaking engagements that further elevated his professional standing.
| Benefit Category | Impact | Result |
| Brand Recognition | Nationwide exposure | Increased bookings |
| Employee Relations | Improved morale | Better retention |
| Industry Standing | Enhanced reputation | Leadership opportunities |
| Company Value | Positive PR | Higher valuation |
Career Impact Points:
- Enhanced public image significantly
- Strengthened employee relationships
- Increased Diamond Resorts bookings
- Opened political opportunities
Other Work, Charity & Politics
Political Involvement
Stephen Cloobeck political career includes consideration for Nevada governor in 2007 and active participation as a Nevada political donor. His California governor race 2026 candidacy announcement in November 2024 signals serious gubernatorial ambitions, promising to leverage business acumen for public service.
As Stephen Cloobeck governor campaign gains momentum, he emphasizes economic development and tourism industry expertise. His platform focuses on job creation, business-friendly policies, and leveraging California’s natural assets to strengthen the state’s position as a premier destination for residents and visitors alike.
Political Milestones:
- Considered Nevada governor run (2007)
- Active political donor
- California governor candidate (2026)
- Travel Promotion Board Chairman
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Philanthropic Contributions
Philanthropic contributions Cloobeck include founding the Brent Shapiro Foundation for Drug Awareness, addressing addiction through education and prevention programs. His charitable work demonstrates commitment to social causes beyond business success, impacting countless families affected by substance abuse issues.
Stephen Cloobeck social media often highlights charitable initiatives, including a significant endowment to Brandeis University International Business School in 2012. These business philanthropy in America efforts reflect his values and desire to give back to institutions that shaped his path.
| Charitable Work | Focus Area | Impact |
| Brent Shapiro Foundation | Drug awareness | Prevention programs |
| Brandeis University | Education | Business school endowment |
| Nevada Cancer Institute | Healthcare | Board chairman |
| Community Initiatives | Various | Ongoing support |
Philanthropic Highlights:
- Founded drug awareness foundation
- Major university endowment (2012)
- Nevada Cancer Institute board
- Active community supporter
Business Leadership Roles
Stephen Cloobeck businessman serves as Chairman of the Board for the U.S. Corporation for Travel Promotion and Nevada Cancer Institute. These business leadership spotlight positions demonstrate his influence extending beyond hospitality into healthcare and national tourism development initiatives.
His travel promotion board chairman role shapes America’s tourism strategies, promoting domestic and international travel. These leadership positions showcase diverse expertise and commitment to industries beyond personal business interests, contributing valuable insights to national economic development.
Leadership Positions:
- US Corporation for Travel Promotion (Chairman)
- Nevada Cancer Institute (Board Chairman)
- Various advisory boards
- Tourism industry advocate
Stephen Cloobeck Personal Life
Stephen Cloobeck Wife
Stephen Cloobeck spouse history includes two marriages. His current relationship status remains private following his 2018 divorce. Stephen Cloobeck family life has been marked by long-term commitments, with both marriages lasting over a decade each.
Stephen Cloobeck personal life occasionally surfaces in media coverage, particularly regarding his high-profile relationships and subsequent legal matters. Despite public attention, he maintains focus on family relationships, especially with his children from his second marriage.
Marital History:
- First wife: Heather (13 years)
- Second wife: Chantal Leduc (1997-2018)
- Current status: Divorced
- Total children: Three
Stephen Cloobeck Ex-Wife
Chantal Leduc Cloobeck was Stephen Cloobeck wife from 1997 to 2018. A Canadian model who won Star Search in 1993, Chantal shared over two decades with Stephen, raising three children together before their separation.
The Stephen Cloobeck divorce settlement involved substantial assets. Chantal Leduc divorce terms included the Laguna Beach mansion worth $40 million, purchased for $10.5 million in 2007. This real estate dispute after divorce represented one of multiple assets divided after their lengthy marriage.
| Marriage Details | Information |
| Spouse Name | Chantal Leduc |
| Marriage Year | 1997 |
| Divorce Year | 2018 |
| Duration | 21 years |
| Children Together | 3 |
| Major Asset | Laguna Beach mansion ($40M) |
Divorce Highlights:
- Marriage lasted 21 years
- Chantal received Laguna Beach home
- Divorce finalized in 2018
- Substantial asset division
Stephen Cloobeck Daughter
Stephen Cloobeck children include at least one daughter, though specific details remain private to protect family privacy. Stephen Cloobeck family maintains discretion regarding children’s identities, ages, and personal information away from public scrutiny.
The Stephen Cloobeck profile reveals dedication to fatherhood despite demanding business schedule. He prioritizes family time and ensuring children receive proper education and values, shielding them from excessive media attention while maintaining strong parental relationships.
Daughter Information:
- Identity protected
- Raised privately
- Strong family bonds
- Education prioritized
Stephen Cloobeck Son
Stephen Cloobeck son gained indirect mention in legal documents related to the Stefanie Gurzanski controversy, specifically regarding his bar mitzvah yarmulke. This Stephen Cloobeck personal life detail highlighted the intersection of private family matters with public legal disputes.
Stephen Cloobeck children remain largely shielded from public attention. His son’s religious ceremonies and personal milestones are kept private, demonstrating Stephen’s commitment to protecting his children’s childhood despite his public persona and celebrity net worth comparison scrutiny.
Son Details:
- Identity private
- Had bar mitzvah ceremony
- Protected from media
- Strong father-son relationship
Stephen Cloobeck Children Overview
Stephen Cloobeck children total three from his marriage to Chantal Leduc. Stephen Cloobeck family life emphasizes normal upbringing despite extraordinary wealth, with children educated at prestigious institutions while maintaining grounded values and strong family connections.
As a father, Stephen Cloobeck businessman balances demanding career with parental responsibilities. His Stephen Cloobeck biography demonstrates commitment to being present for major milestones, ensuring children understand both privilege and responsibility that comes with their family’s success.
| Family Overview | Details |
| Total Children | 3 |
| Mother | Chantal Leduc |
| Privacy Level | High |
| Parenting Style | Present and protective |
| Education | Private institutions |
Parenting Approach:
- Three children total
- Privacy highly valued
- Quality education provided
- Balanced upbringing emphasized
OnlyFans Girlfriend & Legal Controversy
Relationship With Stefanie Gurzanski
The OnlyFans lawsuit Stephen Cloobeck case began with his 2020 relationship with Stefanie Gurzanski, an OnlyFans model. They met through a matchmaker, with Stefanie Gurzanski lawsuit documents revealing he spent approximately $1.3 million during their five-month relationship.
High-profile celebrity lawsuits details include a lavish $130,000 birthday party at his Cabo San Lucas luxury home for her 26th birthday. The millionaire dating scandals intensified when allegations emerged that she demanded $2 million cash plus a $7 million house in exchange for abandoning OnlyFans.
Relationship Timeline:
- Started: 2020
- Duration: 5 months
- Birthday party cost: $130,000
- Birthday gift: $200,000
- Total spent: $1.3 million
Lawsuits & Restraining Order Details
Stephen Cloobeck lawsuit details emerged in January 2021 when he sued Stefanie for fraud and trespassing. The Stefanie Gurzanski restraining order followed her claims of fearing for her safety, with the court granting protection after heated exchanges.
OnlyFans model controversy centered on unauthorized nude photos taken throughout his properties, including his private jet Bombardier Global Express, Beverly Hills mansion Papillon, and Las Vegas hotel suite. One particularly offensive incident involved posting a photo wearing his son’s bar mitzvah yarmulke on Rosh Hashanah.
| Legal Action | Date | Details |
| Initial Lawsuit | January 2021 | Fraud, trespassing claims |
| Amended Complaint | February 2021 | Property return demanded |
| Restraining Order | 2021 | Granted to Stefanie |
| Photo Controversy | Throughout 2020 | Unauthorized OnlyFans content |
Legal Controversy Points:
- Fraud allegations filed
- Unauthorized photos throughout properties
- Religious insensitivity incident
- Restraining order granted
- Property return demanded
Stephen Cloobeck Luxury Real Estate
Beverly Hills Mansion “Papillon”
Beverly Hills mansion Papillon represents Stephen Cloobeck real estate crown jewel. After purchasing land for $19 million, he spent years obtaining city approval to construct the 16,000-square-foot estate, finally receiving permits in February 2017 for this architectural masterpiece.
The expensive Beverly Hills properties listing includes “Papillon,” French for “butterfly.” Stephen Cloobeck mansion value is self-reported at $100 million, featuring cutting-edge design, luxury amenities, and panoramic views that justify the extraordinary valuation in one of America’s most exclusive neighborhoods.
Papillon Details:
- Land purchase: $19 million
- Square footage: 16,000
- Approval year: 2017
- Claimed value: $100 million
- Name meaning: “Butterfly” (French)
Cabo San Lucas Estate
Cabo San Lucas luxury home serves as Stephen’s Mexican retreat, reportedly valued at $45 million. This celebrity beachfront mansions property hosted Stefanie Gurzanski’s controversial birthday celebration and represents one of multiple international properties in his portfolio.
The multi-million dollar homes collection includes this beachfront paradise featuring private beach access, infinity pools, and world-class amenities. Real estate value appreciation in Cabo has likely increased the property’s worth significantly since original purchase.
| Property | Location | Value | Features |
| Papillon | Beverly Hills | $100M | 16,000 sq ft estate |
| Beach Estate | Cabo San Lucas | $45M | Beachfront luxury |
| Former Home | Laguna Beach | $40M | Went to ex-wife |
| Other Properties | Las Vegas | Undisclosed | Multiple holdings |
Cabo Estate Features:
- Beachfront location
- $45 million valuation
- Private resort amenities
- Frequent entertaining venue
Former Laguna Beach Mansion
The Laguna Beach mansion purchased for $10.5 million in 2007 appreciated to $40 million by the divorce settlement. Chantal Leduc divorce terms awarded her this luxury architecture in California property as part of their asset division.
This real estate value appreciation example demonstrates Stephen’s investment acumen. The oceanfront estate’s nearly 400% value increase over 11 years reflects both market conditions and property improvements made during their marriage before the eventual settlement.
Laguna Beach Property:
- Purchase year: 2007
- Purchase price: $10.5 million
- Divorce value: $40 million
- Appreciation: Nearly 400%
- Current owner: Chantal Leduc
Conclusion
Stephen Cloobeck net worth Forbes discussions continue as he pursues California’s governorship in 2026. His journey from Brandeis University alumni to timeshare industry mogul demonstrates exceptional business acumen, with the Diamond Resorts sale value of $2.2 billion cementing his legacy in hospitality and his personal $500 million fortune.
Whether the Stephen Cloobeck billionaire claim holds true or not, his impact on travel, charity, and business remains undeniable. From Undercover Boss fame to philanthropic contributions Cloobeck makes through various foundations, his story exemplifies American entrepreneurship while his California governor race 2026 candidacy promises an intriguing next chapter in this remarkable life.
