'Undercover Boss' Reveals The 'Most Generous' CEO Of All

Without fail, the CEOs featured on "Undercover Boss" lavish their employees with extravagant gifts and promotions. But there's been a good deal of skepticism about how genuine these bosses actually are about helping the rank-and-file. This past Friday, the CBS reality series devoted the episode to celebrating "Epic Bosses," and Stephen Cloobeck, the founder and chairman of Diamond Resorts, arguably stole the show.

Cloobeck -- the only boss to undergo the " 'Undercover' journey" twice -- has contributed $2 million to his workers, $1 million of which came from his own pocket. He's paid for a worker's life-saving cancer treatments, as seen in the video above. And he's also created a special crisis fund for all his 5,600 employees. (He announced this during his second appearance earlier this season.) "I realized I couldn't just give to a couple of members [of my resorts]," he said on Friday's episode. "'Being on 'Undercover Boss' changed my life forever. ... I learned it's important to take care of as many people as possible."

Viewers of the episode tweeted their approval. "Stephen J. Cloobeck is an amazing person," tweeted Nevi Lawrence (@nevilaaa). "ATTABOY Stephen!!!," tweeted another, Stacey Bracey (@thebracygroup).

As viewers learned Friday, the fund literally has saved lives. A salesman for Diamond Resorts named Jacob appeared on the special episode, even though he did not take part in Cloobeck's other appearances on the show. Dressed in a suit, and with a full head of hair, Jacob told the camera that the last time he visited the company's corporate office he was "completely bald," as a result of treatment for a complex and rare cancer that he didn't name. The disease required the attention of the No. 1 oncologist in Las Vegas, Jacob said, which he was able to afford thanks to the crisis fund.

"Without that help, I wouldn't be here today," Jacob said, "I'd be dead."

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

But as noteworthy as Cloobeck's generosity is in its own right, perhaps the real reason that he stands out is because that attitude seems to stand in such stark contrast as income inequality grows sharply in corporate America. (The average American CEO earned $12.3 million in 2012, 354 times more than the average worker, according to the AFL-CIO, the largest federation of trade unions in the country.) Meanwhile, Diamond Resorts' average salary for it workers --$42,775 -- is on par with the average salary among all workers in the U.S., according to the salary information website, Glassdoor. (Cloobeck's annual salary is not publicly available, as Diamond Resorts is a privately held company. But his net worth is estimated to be $100 million, according to Celebrity Net Worth, an online digest of celebrities' financial information.)

The lengths that Cloobeck had gone to simply overshadowed those of other bosses who took their turn on the "Epic Bosses" episode, as they described minor shifts they'd made at their companies. Subway now invites its workers to pitch sandwich ideas, the company's chief development officer, Don Fertman, announced. And Rick Silva, the CEO of Checkers and Rally's, announced a new gift of $15,000 to workers there who turned around a branch that he shut down during his appearance.

But with so many U.S. workers toiling at or around the minimum wage, if they are lucky enough to have work at all, it wouldn't be surprising if viewers weren't so impressed by these execs' change of heart. Case in point: Thanks to appearing on "Undercover Boss," Sheldon Yellen, CEO of Belfor, a property-restoration company, told the cameras Friday that he feels more in touch with his workers -- so much so that he now wants to take public transportation.

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I love this guy, he is great!...

September 01 2015 at 9:52 PM Report abuse rate up rate down Reply

After seeing undercover boss has such respect for this man.Wise and has such a good heart.Some CEO on the show put money to improve the company.But this man not only done that. But out of all the shows CEO gave most money for the people that work for him
To all the haters, Dont be so jealous of the man.If you was in his shoes would you be so generous? Or would the money go to *****, gambling, drinking drugs?.

September 10 2013 at 12:44 AM Report abuse rate up rate down Reply

I'd like to see this show come to my company and do this, these big wigs forget what it's like to be the peons making them rich because w/o all these low paying workers they wouldn't have a company or all their $$$ . If my company had a call in sick out day.... of the 65,000 plus workers on a holiday no less.... I'd like to see what the CEO/management/department heads would do.....the place wouldn't be able to open safely! I work for the largest, most recognizable profitable entertainment companies in the world, based in Florida it is the largest company employing over 65,000 people. Yet it has been nationally reported to be the second, behind Comcast as one of the lowest paying companies since it's inception in1971! Steadily over the years the morale and company image has declined, but it starts at the top and they need to get out there like this show has them do to see and live it and be aware of what is happening, otherwise they have no one else to blame for the decline of the business but the management, or lack of knowledgeable managers or caring supervisors that know what the job entails, there is no respect and no incentives....it is a sad world when a place that people come to and save for years to bring their family on vacation plus just want to forget the real world and be a "kid" again, should have the best the company can offer yet the business is lacking in experience and knowledge of it's product and when you barely make above minimum wage, work double shifts yet still can't pay your bills and enjoy a balanced, work/family life something is wrong and someone needs to open their eyes and stop being so greedy, $$$ has always been the root of all evil, these bosses forget how they earned all that $$$ and it wasn't by their own doing! The "happiest place on earth" needs to wake up and see what is happening internally or they may all be out of work someday.....

May 25 2013 at 7:42 AM Report abuse rate up rate down Reply
1 reply to my2000pony's comment

And you would think that they care, not, they look to replace older employees by fresh kids earning low wage salaries, so they can cash in on the deal., just like the stock market buy low and sell high.

February 10 2014 at 6:55 PM Report abuse rate up rate down Reply

....CEO's are the most overpaid people on the earth....they should give back to the folks that do the real work.

May 23 2013 at 9:55 AM Report abuse +1 rate up rate down Reply

Diamond Resorts is a pyrimade scheme. Fees are paid on points. These fees are in no way what the points are worth. A silver member (15000 points) was able to defer fees by useing points, but this is no longer true. In order to use points to cut fees you must be a gold member (30000 points). At almost $1.00 per point cost to obtain the additional points but only worth .05/point in fees payment when they charge anywhere between .12 to .17 per point in yearly fees for you to use them. This is a total ripoff. NOW he uses these collected fees to setup plans for employees. And now I hear that the yearly fees will be going up. RIPOFF

May 22 2013 at 9:47 PM Report abuse rate up rate down Reply

i think this show is a piece of crap and why good shows are bieng cut so shows like this can be on is really us being screwed by the man just in a different way

May 22 2013 at 8:18 PM Report abuse rate up rate down Reply

i guess it's a start, $2 million to his workers, and he's created a special crisis fund for all his 5,600 employees.
I learned it's important to take care of as many people as possible." he should of stated, all of his employees as possible,
$2,000,000 div by 5,600 = $357 each, how far will that go, hopefully the employees will not need to much,
how about better pay, health plan and benefits, just the one person who had cancer, which is very expensive, probably took a big chunk out of it, also, how long does a person have to work there to be eligible

May 22 2013 at 2:18 PM Report abuse -2 rate up rate down Reply
1 reply to impactvqi's comment

It's a very large company, I am SURE they have benefits. He didn't NEED to donate that, you know. Besides that, 5,600 people are not going to have a **crisis**. Contracting stage four cancer, is a crisis. Paying off your Miata is not.

May 22 2013 at 5:13 PM Report abuse +1 rate up rate down Reply
The Riley's

Can anyone please tell me why corporate CEO's are suddenly the bad guys in America. Can any of you complaining snivel nosed brats tell me what you have done to improve the lives of your fellow citizens. I didn't think so. Corporate America has provided you with the opportunity to live the life you now enjoy, and you are probably living it due to the hard work of some other American. Most of you have no idea what it would be like if it wasn't for the leadership of those greedy CEO's. I just returned from a trip to several Asian countries and you can see the devastating poverty of the people who live in countries that think Capitalism is evil. If you are smart, take risks, and provide great leadership you should be greatly rewarded. When was the last time you worked for a poor person. Although I would bet that most of you are receiving your livelihood from a organization that is essentially bankrupt, The United States Government. What will you do when they can no longer afford to support you in the life style your have become accustomed to?

May 22 2013 at 12:40 PM Report abuse rate up rate down Reply

Great. However if these CEO's were paying the employees the amounts they actually deserved for the work they were doing, they would have already had enough to pay for the things they so desperately need. And what about all the employees not featured on these episodes? They still toil in relative poverty. The show makes it look like the 'boss' is doing something above and beyond when these companies should have been paying more all along. No wonder so many workers are so unhappy at their work and that companies say they can't find 'qualified' workers. I think it would be interesting to see how many 'qualified' workers came out of the woodwork if companies started paying 'qualifying' wages.

May 22 2013 at 12:10 PM Report abuse rate up rate down Reply

Stephen has many good and many bad qualities like most of us. I won't go into either here but what he did on the show was admirable.

May 21 2013 at 2:08 AM Report abuse +2 rate up rate down Reply

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