'Undercover Boss': Stephen Cloobeck, Diamond Resorts' 'Explosive' CEO, Outs Himself Again And Again

'Undercover Boss': Hotel Exec Gives Employee A House, Surgery For Daughter

Stephen J. Cloobeck just can't get enough of "Undercover Boss."

Less than a year ago, the CEO of Diamond Resorts International LLC appeared on the CBS show to kick off the series' third season. During that episode, the high-energy boss distinguished himself by storming off the set, saying the failure of the staff to carry out his policies was "insanity."

On Friday's episode, Cloobeck appeared on the show again -- the first time that any boss had made a return appearance. And Cloobeck -- described by the show's narrator as "the most explosive boss" in the history of the series -- made it clear that his high-octane approach was still his lodestar. As in his first run, Cloobeck couldn't stop from outing himself as the boss -- twice, in fact, after being disappointed by his workers' performance. He also showed extraordinary generosity at the end of the show.

More: 'Undercover Boss': 5 Most Gripping Moments From Season 3

Veronica, a spa attendant at a recently acquired Diamond resort in Mexico, Cabo Azul, was the lucky recipient of the boss's largesse. During a site visit, she met Cloobeck -- whom she'd been told was a former construction worker named Mark Gargos, who was appearing on a reality show in the hope of opening a boutique hotel. She taught "Mark" how to properly operate a blow dryer without scorching the customer. (But he was much more at ease fixing a faucet while working with Marcus, a maintenance worker in Palm Springs, Calif.)

Veronica also told Cloobeck how she and her husband have to work two jobs as they try to save money for their daughter's surgery. Daniela, who was born prematurely, has two hernias. At the end of the show, when Cloobeck's identity already had been revealed (more on that in a moment), he showed some Oprah-size generosity: He told Veronica that he'd pick up the tab for Daniela's surgery.

And buy her a new car.

And a house. (Her reaction is in the video above.)

The first time Cloobeck outed himself in this episode, though, he did so calmly. It took place during the regular taping of the show, well ahead of the reveal. He was working with RK, who works in housekeeping at Cedar Breaks Lodge in Brian Head, Utah, one of the 220 Diamond properties in 28 countries that service 600,000 guests a year.

Immediately upon arriving on the site, Cloobeck was unhappy with what he saw at Cedar Breaks. The resort's landscaping was unkempt and rooms had mold.

It also became clear that Cedar Breaks' managers weren't on top of the situation. RK, a member of the housekeeping staff, told Cloobeck that he alerted the management of on-site problems, but nothing had come of it. And RK said that he'd yet to receive a properly spelled nametag, two years into his job. (The one he wore said "RJ.")

After hearing how RK was also raising a daughter on his own after his wife cheated on him, Cloobeck revealed himself. Very calmly, he then informed RK that he would provide him $25,000 for daycare, and a trust fund for his daughter's schooling that will grow to $50,000.

He was less cool while manning the front desk at Cabo Azul. Working with Stephanie, Cloobeck encountered a series of snafus. He found out that the workers at the front desk take down credit card numbers for reservation authorization, even though, according to Cloobeck, that's a violation of both privacy laws and his company's rules.

Guests also had problems with getting discounts processed, and showed up at the front desk to report their problems while Cloobeck happened to be there. In questioning one guest about her frustrations in getting her discounts processed, Cloobeck decided on the spot to reveal himself and let her know that he wanted to pick up the tab for her son's wedding that just took place at the resort.

Cloobeck initially was curt, however, with Stephanie and the other workers handling the issues at the front desk. "That's a problem for me," was Cloobeck's stern reaction to the shortcomings at Cabo Azul. Very shortly thereafter, though, he assured those employees that he knew it wasn't their fault, that they are just trying to do their job. Speaking to the camera, Cloobeck said that he learned "you can't just throw money at a new resort" and expect results.

Cloobeck showed his more playful side while visiting with Monique, an activities coordinator at one of his resorts in Palm Springs. Before arriving, he'd told the show's TV audience that he hoped his activities coordinator was "bubbly" because the job description is "making sure everyone has a good time."

He was pleased with the way Monique quickly pushed him to lead a dance lesson for guests. It turned out be a rare moment of shyness for Cloobeck. (After dancing, Cloobeck said that he'd felt like a "moron," given his struggles keeping up with the moves that he was supposed to be teaching.) Monique also demonstrated her authority on style and design in giving Cloobeck unvarnished feedback -- telling him that the location's uniforms are dull. And she showed that she had no problem in keeping all the kids in her class in control while handing out ice cream after the dancing session.

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Cloobeck brought his distinctive bravado to the reveal. In addition to his gifts to Veronica, he told Monique that he wants her to design new uniforms for her hotel, and will pay for her to attend fashion school in Los Angeles. He'll also foot the bill for an apartment while she's studying.

And he went even further. He announced to a meeting of his entire staff that he plans to start a crisis fund for them. He will put in $1 million of his own money, and the company with match it.

It was a departure from the usual storyline of the series, in that the only workers who normally have benefited from the boss's generosity were those who actually appeared on the show.

But the question remains: Just how will Cloobeck top himself during his third appearance?

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He should take more care of people who own his properties instead of raising maintenance fees every year since he took over. He's reduced services, taken away hot tubs that were a part of the units when purchased years ago because he can't come up with the money to maintain them. We now get a sun room in its place! Really first class resort is a thing of the past. And then he goes on TV TWICE to throw money around like it's water to make himself look like a great guy. It's all about his grandiosity and his ego that know no bounds. His business practices are a sham! His prices are outrageous and the maintenances costs out of control for years because he's a lousy manager in reality. It's all false and his approach is like medicine men trying to get you to buy the miracle answer to all your problems. Our resort in Virginia has gone downhill and he keeps charging more for less! The only change noticeable at our resort is the number of sales people that try to get you to purchase points from Diamond and the high pressure they use to get you to buy more points at high costs. It's really our money he's throwing around to his staff. He wants to be the next Hilton but he has no clue. Talking service doesn't make it happen and buying an identity is also a cover up for a reality that needs a lot of improvement.

July 11 2013 at 10:58 AM Report abuse rate up rate down Reply

Bill. i was victum of a recient buyout by diamond. they aparently pruchased Monarch resorts. The first notice I recieved stated they had purscased my loan. I had no idea what they were talking about! I called the number on the letter and learnd they had taken over my monarch accoint. After three voice messages to please call me. and many attempts to reach a real person. I was able to contact some one by calling there payment group.who tried to help me find out what was going on. her coment was I had no idea we were that hard to get any information from.
I was very dissapointed with the experiience, but was told there was NO WAY CANCLE A CONTRACT WITH DAIMOND! I really did not want deal with them any further. MY ADVICE TO PONTIAL CUSTOMERS DON'T BECOME ONE I feel the undrecover boss was just a show and refelected little or no reality The company is very well sealed and seems to have little interest in your needs.

January 21 2013 at 7:08 PM Report abuse rate up rate down Reply
1 reply to blgris's comment

Just a suggestion - proofread and spellcheck! I mean, really - I can see why no one acknowledged you!

January 13 2015 at 5:55 PM Report abuse rate up rate down Reply

I wish everyone the best!

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December 06 2012 at 12:48 PM Report abuse rate up rate down Reply

A capitalist with a heart? How could that be? He obviously cares very much about his business, but also his employees - a guy who recognizes happy employees make for a better environment for those who stay at his hotels. It's a win/win situation and it should be taken at face value with nothing more read into it. I'm sure there are many that think he had some ulterior motives but he could have gotten away with giving a lot less cash. A very generous guy.

December 04 2012 at 7:29 PM Report abuse rate up rate down Reply

Hey Stephen why don't you help your resorts in Las Vegas where you actually live? Must be nice to come up from "Daddys'" money..huh!!!

December 04 2012 at 1:26 PM Report abuse rate up rate down Reply

Are we to beleive that people still fall for this???????????

December 04 2012 at 12:31 PM Report abuse rate up rate down Reply

Its great when rich folks make others dreams come true.

December 03 2012 at 10:19 PM Report abuse rate up rate down Reply

He should give evertbody 100k

December 03 2012 at 8:57 PM Report abuse rate up rate down Reply

He's passionate about what he does and that's a good thing. But, he's also passionate about the people who work for him. He demands perfection and so he should, the customer should always come first. Kudos to Mr. Cloobeck for his generosity.

December 03 2012 at 3:06 PM Report abuse rate up rate down Reply

'Undercover Boss': Stephen Cloobeck, Diamond Resorts' 'Explosive' CEO, Outs Himself Again And Again
So, Are the Mexicans now US citizens? Green cards? working here legally? An American should have got the money, not foreigners........The US and a lot of Businesses have got this all messed up........NO MORE FOREIGNERS OR ANY SPECIAL GIFTS ,PRIVEALGES OR ANYTHING....PEOPLE OF THE US ARE REALLY STUPID HELPING THEM OUT AND OTHER COUNTRIES, WHEN WE THE USA NEED TO TAKE CAREOF OUR OWN PEOPLE 1ST, 2ND AND 3RD OF ALL

December 03 2012 at 12:47 PM Report abuse rate up rate down Reply
3 replies to ronnie's comment

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