Last week, MSNBC interviewed a Democratic Party donor, multi-millionaire Stephen Cloobeck. The interview itself gives credence to the fact that wealthy donors’ political views are somehow valuable to the political establishment, as Cloobeck’s dense opinions provide no substantive reason for why MSNBC should be giving him airtime. Indeed, the network’s decision to have him emboldens and normalizes money in politics as a positive.
Cloobeck’s comments during the interview spoke to just how out of touch, spoiled, and egotistic wealthy elites are:
I can tell you if we go far left, I’m out. I’m out. We need middle ground. It drives me nuts. So much so it would make me quit the party. And I’ve made it very clear; I’ll cut your money off. And others will do the same. We’ve had enough. We need a new brand.
During the 2016 election Cloobeck donated $1 million to Hillary Clinton’s Super PAC, Priorities USA; more than $100,000 to the DNC; $296,000 to the Hillary Victory Fund; $500,000 to the Senate Majority PAC; and several smaller donations to state parties and centrist Democrats. This year he’s donated the maximum $2,700 to centrist Democrats, including Senators Tim Kaine of Virginia, Kristen Gillibrand of New York and Sheldon Whitehouse of Rhode Island.
He also endorsed Republican Senator Dean Heller of Nevada for re-election this year, but since rescinded that endorsement because he was surprised Heller voted with other Republicans on several issues like healthcare. Cloobeck, an idiot, clearly has a tenuous grasp on politics.
Cloobeck is trying to swindle the Democratic Party into representing his hyper-capitalistic view of society and he’s acted the same in his business life. He’s the founder and former chairman and CEO of Diamond Diamond Resorts International, which he created to sell predatory vacation timeshares to customers. (Michael Flaskey is the current CEO, a spokeswoman for the company pointed out to me after this story ran.)
Cloobeck appeared on “Undercover Boss” in 2012, to perpetuate a fairy tale redemptive story of the cold hearted multi-millionaire who helped a handful of employees his business had treated poorly. His appearance sparked a backlash from dozens of owners in his timeshare business, who demanded refunds or financial remedies because their investments in Cloobeck’s business were a rip-off, the Las Vegas Review-Journal reported.
“Angry owners created a website, poipuowners.org, to gather information,” the newspaper said. They also started anti-Diamond Resort campaigns using social media.” The New York Times reported in 2016 on the company’s predatory tactics to con customers into buying timeshares that are designed to lose real estate value while the company prospers.
In response to criticism about his MSNBC comments, Cloobeck tried to poor shame his critics and defend his ultra wealth. “When u pay $70mil in tax in a year then you have a right to fight me,” he tweeted. “I’m proud to pay. Work hard and perhaps you can be rich wealthy and not jealous. I am a Democrat. Don’t judge. Work ur ass off.”
And this further revolting commentary: “Creating 20,000 jobs. Taking care of people putting many kids thru college. You must be a Bernie person that wants everything for free. Get a job and ad to the GDP. It’s ok to make money. U will realize when u grow up. Everyone wants to do well.”

Cloobeck’s definition of working hard is coat-tailing off his family’s business and investments. His father, Sheldon Cloobeck, was CEO of the International Resorts Group, who owned nearly half of Las Vegas’ time share industry before his son acquired his company.
The Democratic Party needs to sever ties with donors like Cloobeck who operate multi-million dollar businesses predicated on exploiting workers and ripping off customers. He’s a spoiled elitist brat throwing a temper tantrum at the popularity of Bernie Sanders and progressive views.
Cloobeck and donors like him want to keep the party tied to corporate interests. They favor the massive wealth and income inequality rampant in this country and want to keep wages stagnant as the cost of living soars because it allows them to ratchet up their exploitation of workers.
Cloobeck lives in an alternative reality where Horatio Alger rags-to-riches stories are believed, along with the myth that hard work brings financial success. Millions of Americans work hard, work more than one job, work over 40 hours a week, yet can barely afford to make ends meet and often find themselves buried in debt just to pay for necessary life expenses.
Meanwhile, the crooked Cloobecks of the world thrive with the help of the politicians they carry around in their pockets like loose change.