Trump and the millionaires: How the Republican Party bet on the very, very rich

In Wisconsin, making his second bid for Senate after a near-miss 2012 primary loss, Hovde quickly consolidated Republican support, stumping with an Omega watch on his wrist and introducing himself as a fortunate man whom nobody could buy.

“I don’t need their special interest money, and I won’t take it,” Hovde said in one of his first TV ads, which also adopted an idea from Trump: He would donate his entire Senate salary to charity.

He kept up that theme as his campaign went more negative on Baldwin, demanding that she release her domestic partner’s financial information and suggesting at their only televised debate that the Democrat might be casting votes to enrich herself. According to a summer financial filing, the CEO of Sunwest Bank is worth more than $195 million; Hovde has loaned his own campaign more than $20 million, trimming Baldwin’s fundraising lead before Republican PACs intervened on his behalf.

“You take massive amounts of money from Big Pharma. Your whole campaign is funded by Wall Street, Big Pharma and Big Tech,” Hovde told Baldwin on Friday. “I think drug prices are wildly too high, and I’ll actually do something about it, because I’m not taking Big Pharma’s money.”

Baldwin, during her only in-person chance to respond to his attacks on her relationship, framed Hovde’s attempt to go after her partner’s finances as campaign sleaze.

“Eric Hovde should stay out of my personal life,” she said, “and I think I speak for most Wisconsin women that he should stay out of all of our personal lives.”

Over the weekend, as the senator joined Democrats for canvass launches across the state, she argued that Hovde’s argument about his wealth providing financial independence wasn’t persuading voters. Her campaign had spent months reminding voters of Hovde’s mansion in California’s Orange County; it slapped the slogan “what’s with this guy?” on videos of the Republican, mostly in his failed 2012 bid, saying that farming wasn’t as physically draining as it used to be and that he could support raising the Social Security retirement age.

“He’s trying to buy a Senate seat,” Baldwin told Semafor. “He’s spent, I think, about $20 million of his own wealth. It’s a staggering amount of money, [and] I have to follow the rules to raise dollars.”

Republicans have previously tried to recruit wealthy candidates to spare themselves some fundraising headaches, but Democrats have also proven adept at finding opposition research to turn those assets into liabilities. For every Ron Johnson or Rick Scott, there’s a Dr. Mehmet Oz, who blew $26.7 million on his Pennsylvania Senate bid) or Kelly Loeffler ($23.7 million in Georgia).

And Democrats have embraced their own self-funding candidates, too; the wealthiest sitting senator is Virginia Democrat Mark Warner, and the seat Baldwin and Hovde are fighting for was held for 24 years by the late Milwaukee Bucks owner Herb Kohl.

Still, their case against Hovde is cropping up in other states where incumbent Democrats face personally wealthy challengers.

In a debate this month with Republican Dave McCormick, made $22 million in his last year as CEO of the Bridgewater Associates hedge fund, Democratic Sen. Bob Casey attacked him for “investing in China’s oil companies, managing money for Saudi Arabia’s oil companies.” McCormick hit back that Casey didn’t understand how to create jobs.

In Ohio, as luxury car dealer Bernie Moreno built his Republican campaign against Sen. Sherrod Brown, Democrats went after his wealth — at least $26 million — and the multiple lawsuits filed by former employees who accused Moreno of stiffing them. Moreno has countered by touting his business acumen as a positive alternative to “career politicians who have no idea how anything works,” as he put it to Megyn Kelly this week.

The new breed of Republican thinking about personal wealth in politics is most prominent when it comes to Musk, who the Trump campaign has elevated as a surrogate — a one-man study in how private enterprise can do what the government fails at. Within hours on Monday night, the Trump campaign sent its donor list two Musk-themed texts.

At Musk’s Pennsylvania town halls, open to any registered voter in the state, audiences thrill at his basic offer: Elect the candidate of his choice who will let him remake the administrative state and give his own companies more government contracts.

In Harrisburg, Musk fans asked if he could take one of his flamethrowers to federal regulations (on a live stream), or if his Boring Company might be able to “build an island off the coast of Israel” and relocate Palestinians there, ceding their land claims while giving them a new state.

“Could there be enough rubble in Gaza to do it?” she asked.

“Gaza is a thorny problem indeed,” Musk responded, saying that he didn’t have the solution, but wanted America to disentangle itself from foreign conflicts.

Musk is personally spending more than $75 million to get Trump elected, and to win a role in his administration. Pennsylvanians who attended his events were raring to do it — in part, because they bought into the idea that the wealthiest man in the world is an insurgent working to dismantle a larger machine.

Self-funders don’t guarantee an election victory. Everyone reading this newsletter probably saw a Mike Bloomberg ad in 2020; everyone in South Carolina probably got one from Tom Steyer that year. And Democrats spent most of this year happy that they were defending incumbent senators from wealthy opponents, not politicians with well-known brands.

But non-Democratic voters have historic levels of distrust for politicians, especially young men. While Democrats home in on Trump’s in-person promise to wealthy donors that he will cut their taxes and de-regulate their industries, there are plenty of voters to whom this sounds like a good idea. Why would a government that can’t build rural broadband or high-speed rail after years of funding and tax incentives handle public money better than titans of industry?

So it’s not exactly clear that Republicans’ rich-men campaign brand will fall short this year the way it has in the past. It will depend on how subtly they navigate one fact: Neither party wants to be seen as the home of the billionaire, even if one party feels newly comfortable nominating wealthy people. That explains Musk’s insistence that Democrats are actually bought and paid for by the elites.

On Tuesday, when Barack Obama and Tim Walz campaigned in Madison, Walz mocked Musk as Trump’s “running mate” and said that their alliance would mean new government contracts handed to the world’s richest man.

“He could spend millions to make more than $10 billion on the back end,” said Walz. “Donald Trump, in front of the eyes of the public, is promising corruption.” And in an interview after a weekend campaign stop in Stevens Point, Wis., Sen. Elizabeth Warren said that Musk “and the rest of the billionaires” were showing that they didn’t think the normal rules applied to them.“They think that they get to write just a special set of rules, and get to do whatever they want, because they’re rich,” said Warren. “I think that’s a big part of what’s on the ballot this time around.”

Some Democrats don’t want to see the party pick a fight with Musk, separating him from the self-funders they want to keep out of office.

“Not sure going after Musk is a great play for Dems’ final 2 weeks,” former Maryland Rep. John Delaney, himself a wealthy businessman, wrote on X. “He’s deeply admired as a visionary by many people in tech, which is not a small part of the economy. He’s also not on [the] ballot!!!”