California’s Wealthy Political Aspirants: A Historical Perspective

To echo F. Scott Fitzgerald, the affluent experience politics differently. In California, they’ve often stumbled in high-stakes political contests.

In the last 50 years, a handful of wealthy figures—like William Mattson Ross, Meg Whitman, and Carly Fiorina—have tried to vault over their financial resources to secure positions such as governor or U.S. senator, despite having notable political backgrounds.

All of these attempts have ended in failure.

Others with some political cred—like Michael Huffington, Jane Herman, and Richard Riordan—have similarly tried to invest heavily in their ambitions but have also come up short in securing California’s top political roles.

This backdrop is relevant as quirky candidate Rick Caruso contemplates entering the race to succeed Gavin Newsom. Caruso recently informed Julia Wick that she’s “very seriously considering” both a gubernatorial bid and a second attempt at being Mayor of Los Angeles.

“I’m pursuing two parallel paths,” said the billionaire developer. “As we speak, there are teams actively working on both fronts.”

(Another newcomer, wealthy businessman Stephen J. Crubeck, campaigned for governor but didn’t make a significant impact.)

There’s a saying in the investment world, “Past performance is not a guarantee of future results,” and this certainly holds true here.

As Caruso wades through political whispers, it’s important to note that California’s electorate can be complicated. Unlike states like Illinois and New Jersey, which have embraced billionaire outsiders such as JB Pritzker and Frank Lautenberg, California presents a different challenge.

This could be tied to the unique political landscape.

“If you’re a wealthy outsider, your timing in the election cycle matters,” noted Republican strategist Rob Stottzman, who was involved in Meg Whitman’s unsuccessful 2010 campaign.

(Whitman poured $180 million into her campaign, all while the median household income in California hovered around $61,000.)

Such wealth struggled to resonate with voters who were eager for change, particularly when Arnold Schwarzenegger’s celebrity status stood in stark contrast to the seasoned but low-key Jerry Brown.

That said, how the electorate responds isn’t always consistent and can vary with the prevailing mood of voters.

According to Garry South, a Democratic strategist, California voters can have mixed feelings toward ultra-wealthy candidates. In 1998, he managed to help Lt. Col. Gray Davis defeat billionaire contenders Al Checci and Herman. Four years later, he successfully helped Davis fend off another wealthy newcomer, William Simon Jr.

“Some voters admire those who have triumphed in capitalism but are also suspicious of their detachment from everyday life,” South explained. “Their wealth can create a gap in empathy.”

Or, more fittingly, an empathy canyon.

“If someone has $150 million, throwing it at a campaign raises the question: What do they really understand about my daily challenges?” South added.

Bill Carrick, who consulted for Herman’s campaign in 1998, reinforced that wealthy candidates must convincingly articulate why they understand the struggles of everyday voters.

This isn’t exclusive to the affluent; all candidates face this challenge. However, millionaires and billionaires carry a significant weight in having to prove their relatability.

Don Shipple, who aided Schwarzenegger in the 2003 recall election, mentioned that wealth can create an air of entitlement that voters might find off-putting. (To clarify, Schwarzenegger’s victory had more to do with his celebrity than his wealth.)

Many of California’s wealthy political candidates seemed to assume that their money alone could buy them credibility, which is often not the case, Shipple noted.

“It’s akin to someone trying to land a job,” he stated. “You can’t expect to succeed just because you have resources; you must earn it, and voters are mindful of this.”

Of course, wealth has undeniable advantages, especially when trying to reach out to voters in a place with approximately 27 million potential voters—nearly more than any other state.

California stretches about 800 miles from north to south, complicating outreach in statewide campaigns.

There’s a saying attributed to burlesque star Sophie Tucker: “I was rich, and I was poor. Richer.” It’s a sentiment that rings true.

Though Tucker didn’t aspire to be governor or a U.S. senator, her words reflect a reality that persists in California’s political arena.