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Where are the bosses from 'Undercover Boss' now? CBS's stars muddled in lawsuits and bankruptcy

Meet the top 10 'Undercover Boss' who encountered financial troubles and legal battles
PUBLISHED JAN 2, 2024
On the reality show 'Undercover Boss', top executives go undercover in their own company to gain a better understanding of the workings of their organization (CBS)
On the reality show 'Undercover Boss', top executives go undercover in their own company to gain a better understanding of the workings of their organization (CBS)

LOS ANGELES, CALIFORNIA: The reality television series franchise 'Undercover Boss' was created by Stephen Lambert and is produced in many countries. It first aired in 2009 on the British Channel 4.

The show's format showcases the experiences of senior executives working undercover in their own companies to investigate how their firms are functioning and what can be improved, all these while rewarding honest and hardworking employees. 'Undercover Boss' is a fan favorite for sure.

With an IMDb rating of 5.8/10, this reality series won the Primetime Emmy Award for Outstanding Reality Program in 2013 and 2012. On April 26, 2018, CBS announced the first 'Celebrity Edition' to premiere on May 11, 2018. There have been 11 Seasons up until now.

A high-positioned executive or even the owner of the company goes undercover as an entry-level employee in their own company. The executive or the owner changes his/her appearance and comes prepared with a basic background story so that no employee can uncover the truth.

They spend almost a week undercover, working in various areas of the company's departments, doing different jobs, and might be placed in a different location each day. The owner gets exposed to the harsh reality of his company and as he/she spends time with the employees, they understand their professional and personal lives better. 

At the end of the week, the boss returns to his true identity and calls his preferred employees to the headquarters. The boss then rewards hardworking employees financially or even through promotion. 

The show's producers are in charge of selecting the companies and what jobs the bosses will be assigned. The company has no control over what airs, although a promise is made not to hurt the company's reputation. Neither the company nor the owner receives any grant or even gives money to the CBS show's producer or makers. 

Even though the show claims to be authentic, viewers feel some portions are highly dramatized. CBS' most successful show has embellished and edited parts. Sometimes the producers even push a sob story for the audience to emotionally connect with the employees. It is also reported that the employees are specifically chosen, a suitable match would be someone with an emotional story. Sometimes the employees figure out that it's their boss undercover. Sometimes the jobs are staged.

'Undercover Boss' has 11 Seasons (Facebook/@UndercoverBoss)
'Undercover Boss' has 11 Seasons (@UndercoverBoss/Facebook)

Let us look at the Top 10 'Undercover Bosses' to date.

1.  Checkers & Rally's Fast Food Chain, CEO Rick Silva, Season 3 Episode 4

In the episode, Rick Silva went undercover as an employee and went on a search. However, he was so moved by the horrible behavior of a restaurant manager that he came out from undercover, revealed his identity, and shut down the entire restaurant. While undercover as an employee at one of the branches of Checker's, he shut down the restaurant after learning how rude the location's general manager was to his employees.

He was the CEO of Checkers &Rally's Fast Food Chain for 13 years. He left in February 2020 and was replaced by Frances Allen, who was previously the CEO of Boston Market. He went on to join the Culver's as CEO. 

Rick Silva (Getty Images)
Rick Silva (Getty Images)

2. Bikini Sports Bar & Grill, CEO & Founder Doug Guller, Season 6, Episode 3

Bikini Sports Bar & Grill was a 'breastaurant' as claimed by Doug Guller, who encouraged the waitress to wear a bikini. In the episode, Doug Guller went undercover and fired one employee because she over-served one customer and mentioned her career aspirations. However, the real reason why she got fired was because she refused to wear her bikini on TV.  He even passed sexist comments such as 'It's a big bummer from my point of view." The gender bias grew extreme when he offered a one-employee breast implant. 

This Texas-based company closed down its last restaurant in Austin on December 23, 2018. This restaurant was transformed into a new sports bar and restaurant called BBG which was more family-friendly. 

Doug Gueller undercover for an episode of 'Undercover Boss' (CBS)
Bikini Sports Bar & Grill, CEO & Founder Doug Gueller went undercover on an episode of 'Undercover Boss' (CBS)

3. Family Dollar, President and COO Mike Bloom, Season 5 Episode 7

The president and COO of the discount chain Family Dollar,  Mike Bloom, was fired during an episode of 'Undercover Boss'. He was fired by a warehouse supervisor because he was unable to safely operate a forklift. Rosali, the supervisor in the Virginia warehouse, fired a man he thought his name was Mark. Mike was undercover as Mark, an employee, and made several mistakes which led him to be fired. 

He said even though it is a little embarrassing for him he's glad that the supervisor takes the job very seriously. However, Mike Bloom left Family Dollar in 2014. He later joined the Executive Leadership Team as CMO at GPM Investments. Before that, he served as CEO of Fed's Inc.

Mike Bloom in an episode of 'Undercover Boss' (CBS)
Mike Bloom in an episode of 'Undercover Boss' (CBS)

4. Mayor of Pittsburg, Bill Peduto, Season 6, Episode 2

The mayor, Bill Peduto, was told by the District Attorney's Office that it may have been illegal for the mayor to give money to city employees. 

Mayor Peduto gave around $150,000 in checks to city employees he worked with while in disguise. 

His second term as mayor ended in 2022. 

Bill Peduto (Facebook/BillPeduto)
Bill Peduto (Facebook/BillPeduto)

5. Armando Montelongo Companies, Armando Montelongo, Season 6, Episode 10

Armando Montelongo is an American real estate entrepreneur and public speaker known for his role in Flip The House. He is the chief executive officer of the Armando Montelongo Companies, in the episode he hired a body double to help conceal his identity while undercover. 

Montelongo was sued in Texas by nearly 200 plaintiffs. They allege that he used his company’s $1,500 seminars to rope students into paying for more classes, costing them as much as $54,000.

Armando Montelongo (Instagram/@armandomontelongo)
Armando Montelongo (@armandomontelongo/Instagram)

6. Modell's Sporting Goods, CEO Mitchell Modell, Season 4, Episode 1

CEO Mitchell Modell went in disguise into his own stores to see things from an employee's perspective. He was later, accused in a lawsuit by rival Dick's Sporting Goods of entering a Dick's store in disguise to gain access to their retail secrets. A lawsuit was filed by Dick's Sporting Goods and alleged that Modell told Dick's store manager that he was a senior vice president of Dick's, visiting to gather information and meet with Dick's CEO Edward Stack.

The family-owned chain store, Modell's Sporting Goods filed for bankruptcy in 2020. Mitchell Model tried to crowdsource funds but he couldn't manage.

Mitchell Modell (Twitter/@mitchmodell)
Mitchell Modell (@mitchmodell/Twitter)

7. Belfor Property Restoration, CEO Sheldon Yellen, Season 2, Episode 14

In the episode, CEO Sheldon, disguised as Tom Kelly, flew from Detroit to Tulsa so that he could deliver a surprise to an admirer. He surprised Iowe employee Aaron Beck, a fan of the reality show 'Undercover Boss'. Shortly, after the episode aired Aaron from Tusla, Oklahoma, began writing letters about how much he loved the episode and how the CEO treated his employees.

Currently, in 2023, Sheldon Yellen is still the CEO of Belfor Property Restoration.

Sheldon Yellen (Getty Images)
Sheldon Yellen (Getty Images)

8. Shopper's World, CEO Sam Dushey, Season 7, Episode 3

His entrepreneurship and love for business have flourished since the age of fifteen. He was also deemed one of the most successful entrepreneurs in the industry. 

Back in January 2016, in an episode of 'Undercover Boss' Sam Dushey went undercover and met Nalini, an employee in Shopper's World for eight years. Dushey revealed at the end of the episode that it was Nalini who made him realize that employees weren't treated properly. He then gave her more hours and $15,000 as a bonus. He also promised her a $20,000 check for her wedding. 

However, the company did not give Nalini the money. The company in turn sent an explosive mail to her stating it was Nalini who failed to submit invoices requested from various vendors for her wedding. 

Sam Dushey is still serving as the CEO of Shopper's World.

Sam Duschey (samdushey)
Sam Dushey (samdushey)

9. Diamond Resorts, Stephen Cloobeck, Season 4, Episode 4

Steven J Cloobeck went undercover and he focused mainly on properties that Diamond Resorts International acquired from bankrupted Pacific Monarch Resorts.

Stephen Cloobeck is the founder and former CEO of Diamond Resorts, under his leadership, the company experienced tremendous growth and became one of the largest hospitality companies in the world. His net worth is close to $100 million. 

He left Diamond Resorts in 2016 to pursue other business ventures and still remains a Democratic donor and local philanthropist. 

Stephen Cloobeck (Blostephencloobeck)
Stephen Cloobeck (Blostephencloobeck)

10. Rick Forman, Forman Mills, Season 6, Episode 8

Rick Forman is the founder and CEO of New Jersey-based Forman Mills. In the episode, he goes incognito among his staff posing as a contestant on a television reality show.

Forman Mills fought off bankruptcy in 2023 but faced new legal challenges. It even laid off 119 employees, without notice, due to such severe economic circumstances. Now he is involved in a legal tussle as state law in New Jersey requires employers with at least 100 employees to give workers a 90-day notice and pay severance of at least one week's pay for every year of their service. 

Rick Forman (Twitter/@RickForman)
Rick Forman (@RickForman/Twitter)

The former 'Undercover Bosses' surely have big battles to fight!

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