As Elon Musk steps up his work on behalf of former President Donald Trump, Kamala Harris is calling in her own billionaire, Mark Cuban, to reprise the role he played for Hillary Clinton in 2016 by holding a series of high-profile appearances alongside the vice president and her husband this week.
Cuban appeared with Harris in Wisconsin on Thursday and is set to hold a town hall for her Saturday in Phoenix before heading to Michigan the following day to campaign alongside Second Gentleman Doug Emhoff.
“This election is a battle for entrepreneurs,” Cuban said in La Crosse, Wisconsin, on Thursday, before warning that Trump’s trade and tariff policies will drive up prices, ruin Christmas by making gifts more expensive and “crush the dreams” of entrepreneurs by making their costs unsustainable.
“Donald Trump is the Grinch that wants to steal your Christmas,” he said. “The Grinch doesn’t understand how tariffs work… The Grinch is the one that’s going to be putting these small business out of business.”
The “Shark Tank” star, who did not respond to a request for comment, brings business credibility, tech-savvy pop culture appeal, and a maverick persona that is seen as especially appealing to young men, who have become one of the most hotly contested demographics in an election that has seen the gender gap grow to historic proportions.
Harris — whose campaign linked Cuban’s tour to its engagement with male voters — has recently appeared shows like “All The Smoke“, “The Breakfast Club” with Charlamagne Tha God. The campaign has also run ads on platforms with male-skewing audiences, such as gaming site IGN, major sporting events and sports talk radio.
Though Cuban has downplayed the need for Harris to target men, he could be integral to those efforts and has already been making the case for Harris in a semi-official capacity in podcasts and media interviews.
He’s also been an emissary to the business world, helping found a group called Venture Capitalists for Kamala, which now has almost 900 signatories, as well as Business Leaders for Harris.
Cuban’s effort comes as Musk, the CEO of Tesla and SpaceX and one of the world’s richest men, has been appearing alongside Trump, himself a billionaire, and is now holding a series of “conversations” with voters in Pennsylvania separate from the campaign.
Unlike Musk, who has donated nearly $75 million and counting to Trump-aligned groups, Cuban is not a political donor. Federal Election Commission records show a single, $1,000 donation to Rep. Zoe Lofgren, D-Calif., in 2022 under Cuban’s name.
But Harris allies say Cuban’s voice and persona is more valuable than his money.
For instance, a new survey from Equis Research, which focuses on Latino voters, found Cuban to be the most popular figure it tested among Hispanic men under 50, with a net favorability rating 15 percentage points higher than Musk’s.
Ben Wikler, Wisconsin’s Democratic Party Chair, praised Cuban’s “talents” and said he has credibility to reach voters on business and economic issues. “His many fans — including fans of Shark Tank and aspiring entrepreneurs across Wisconsin — know that he means what he says and says what he means,” Wikler said.
Cuban has warned Musk not to trust Trump.
“[Trump] will burn everything he touches. He doesn’t care,” Cuban told NBC News host Chuck Todd. “I said to Elon, ‘There’s going to come a time when you need something from Donald Trump and he’s going to disappoint you. Guaranteed.’”
The 6’2” former NBA team owner (he recently sold his majority stake in the Dallas Mavericks, but retains a smaller portion of the team) is comfortable and confident on platforms that appeal to men, but that other Democrats typically avoid, such as “All-In,” the podcast popular with anti-woke Silicon Valley types.
In a recent appearance on comedian Theo Von’s hugely popular podcast, Cuban gamely dropped f-bombs, joked about disgraced hip hop mogul Diddy and knifed Trump with a smile to a host who is a fan of the president and had him on as a guest a few weeks earlier.
“I like the guy, if he was here and we were just talking s—, I’d get along great with him. But that’s different from wanting him to be President of the United States again,” Cuban told Von. “I think you need someone you can trust. Is Kamala perfect? No. Do I agree with everything she’s going to do or says or do? No. But I trust her.”
None of this, however, is unfamiliar territory for Cuban, who played a similar role in 2016 for Clinton’s ultimately unsuccessful campaign against Trump.
That year, Democrats were thrilled to watch Cuban taunt and insult his fellow billionaire-turned reality TV star in ways that Clinton herself would never dream of doing in public, questioning if Trump was really a billionaire and saying he was unfit for office.
“I got at least twice as much money as him,” Cuban said on Stephen Colbert’s show, before running through a set of insult comedy jokes about the size of Trump’s hands, his multiple bankruptcies and his “shiny, orange” appearance.
“Donald, the only way you’re worth $10 billion is if I paid you $9.5 billion to wash my balls!” Cuban said as the audience cheered like background actors in the “You Got Served” film franchise.
Democrats loved that Cuban seemed to be able to get under Trump’s skin. Clinton invited him to sit in the front row of one of her debates with Trump.
“If dopey Mark Cuban of failed Benefactor fame wants to sit in the front row, perhaps I will put Gennifer Flowers right alongside him!” Trump tweeted ahead of the debate, referencing a woman who claimed to have an affair with Bill Clinton before his 1992 presidential run.
Before that campaign, Trump and Cuban had a hot-and-cold relationship. In 2014, Trump tweeted that he had “far greater wealth and athleticism” than Cuban. In another tweet that year, he called Cuban “an asshole” and said “Major League Baseball was really smart when they wouldn’t let Mark Cuban buy a team.”
Cuban has toyed with the idea of running for president himself — Trump tweeted in 2017 that Cuban is “not smart enough to run for president!” — though Cuban last year shut down the idea of running in 2024.
Still, not all Democrats are thrilled to see the party’s leaders bring a billionaire on the campaign trail.
Cuban, after all, has his own agenda and some on the left question what he might want from a potential Harris White House
“Mark Cuban is a talented communicator, and I get why having a billionaire reality TV show personality combat Donald Trump holds appeal to the campaign. But billionaire tech bros often have a lot in common,” said Jeff Hauser, founder of the Revolving Door Project, a progressive group focused on personnel appointments to key economic policy positions.
Cuban has called for the removal of the head of the Security and Exchange Commission over his approach to cryptocurrency regulation and has said he would be interested in the job for himself.
“Head of the SEC, head of the SEC, that’s the job I would take,” he said last month when asked by a Fox News host if he would entertain taking a job in a Harris administration. He added that “maybe” he would consider being in charge of the Department of Health and Human Services as well.
He’s also called for removing Federal Trade Commission Chair Lina Khan, a hard-charging progressive darling, prompting Rep. Alexandria Ocasio- Cortez, D-N.Y., to declare there would be “an out and out brawl” if “billionaires [who] have been trying to play footsie” with Harris push for her removal.
“Harris’ paid ads reflect a populist bent on economics, but it is worrisome that Cuban might be able to instead elevate plutocratic aims within a Harris Administration at odds with her ads by dint of personal charisma.”
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