gubernatorial campaign

The rich, to paraphrase F. Scott Fitzgerald, are different. In California, they lose a lot of very expensive, very high-profile political races.

Over the past 50-plus years, a half-dozen fabulously wealthy men and women — William Matson Roth, Meg Whitman, Carly Fiorina among them — have clambered atop their hefty cash piles and, despite any significant political experience, tried to launch themselves into the office of governor or U.S. senator.

Every last one of them failed.

Others with at least some background in elected office — Michael Huffington, Jane Harman, Richard Riordan to name a few — sunk a goodly chunk of their fortunes and came up similarly short in their efforts to win one of California’s top two political posts.

That history is worth noting as the very-well-to-do Rick Caruso eyes a possible entry into the wide-open race to succeed Gavin Newsom. Caruso recently told my colleague Julia Wick he was “very seriously considering” both a gubernatorial run and a second try for Los Angeles mayor.

“I’m running down two parallel paths,” the billionaire developer said. “As we speak, there are teams very busy working on both of those paths.”

(Wealthy businessman Stephen J. Cloobeck, another political first-timer, has been campaigning for governor for months, spending liberally to little avail.)

There’s a common disclaimer in the field of investment — “past performance is no guarantee of future returns” — which certainly applies here.

Still, as waiting-for-Caruso replaces waiting-for-Kamala among political gossips, it’s worth asking whether there’s something — floating in the air, mixed in the water or soil — that has made California such an inhospitable place for so many lavishly monied candidates. Unlike, say, Illinois or New Jersey, which elected billionaire neophyte JB Pritzker and multimillionaire Frank Lautenberg, as, respectively, governor and U.S. senator.

Part of the reason could be the particular political climate.

“If you’re the rich outsider, you have to show up in an election cycle where people want the outsider,” said Rob Stutzman, a Republican strategist who worked for Meg Whitman’s failed 2010 gubernatorial campaign, which cost a cool $180 million.

(Yes, $180 million. The former tech CEO coughed up most of that sum at a time California’s median household income was about $61,000.)

All that lucre couldn’t override the prevailing sentiment among discontented voters who were ready, after nearly eight years of the uber-outsider Arnold Schwarzenegger, to embrace the tried-and-true experience of the reemergent Jerry Brown.

That said, there’s a lengthy enough record of futility to suggest more is at work than the changeable mood of a fickle electorate.

Garry South believes California voters are of two minds when it comes to super-rich candidates. In 1998, the Democratic strategist helped Lt. Gov. Gray Davis maneuver past two moneybags, billionaire former airline executive Al Checchi and Rep. Harman, to win the governor’s race. Four years later, South led Davis’ successful reelection campaign against another multimillionaire newcomer, William Simon Jr.

“Part of them kind of admires someone who went out and made a killing in our capitalistic society … and walked away filthy rich,” South said of voters’ dueling impulses. “But they also have a suspicion that, because of their wealth and because of the benefits that it confers on that person, they don’t really know how the average person lives.”

Call it an empathy gap.

Or, perhaps more aptly, an empathy canyon.

“If somebody has $150 million sitting around they can dump into a campaign for public office,” South said, channeling the skeptical sentiment, “what understanding do they have of my day-to-day life?”

Bill Carrick, a consultant for Harman’s 1998 campaign, agreed it’s incumbent on a rich candidate to “have something substantive to say and be able to articulate why you’re going to make people’s lives better.”

That’s no different than any other office-seeker. But unlike less affluent, more relatable candidates, a billionaire or multimillionaire has a much heavier burden convincing voters they know what they’re talking about and genuinely mean it.

Don Sipple, who helped elect Schwarzenegger governor in California’s 2003 recall election, said wealth often comes with a whiff of privilege and, even more off-putting, an air of entitlement. (To be clear, Schwarzenegger won and replaced Davis because he was Arnold Schwarzenegger, not because of his personal fortune.)

A lot of California’s failed rich candidates, Sipple said, appeared viable — especially to political insiders — “because of their money. And they really didn’t have anything to offer beyond that.”

“It’s the same as somebody who goes out and tries to earn a job,” he went on. “You never deserve it. You’ve got to out and work for it. And I think voters make the distinction.”

Of course, wealth confers certain advantages. Not least is easy access to the extraordinary sum it takes to become well-known in a place with more eligible voters — nearly 27 million, at last count — than the population of all but a handful of states.

California is physically immense, too, stretching approximately 800 miles from north to south, which makes costly advertising the only realistic way to communicate in a statewide top-of-the-ticket contest.

There’s another old aphorism about wealth, credited to the burlesque star and actress, Sophie Tucker. “I’ve been rich,” she famously said, “and I’ve been poor. Rich is better.”

That’s undeniably true, so far as it goes.

The singer and comedian never tried to be governor or a U.S. senator from California.

The Democrats running for California governor have spent the spring and summer working to win over the powerful donors and interest groups who could help them squeak through a competitive primary election.

But the candidates, and many deep-pocketed Democrats, are still waiting for the decision that will have the biggest impact on the race: whether former Vice President Kamala Harris is running.

Since Harris lost to President Trump in November, the race to replace Gov. Gavin Newsom has been in suspended animation, with candidates trying to plan their campaigns without knowing who their biggest opponents will be. A few are making contingency plans to run for other offices. And some major donors are waiting to write big checks.

“It creates a little bit of a limbo situation,” said Tony Thurmond, the state superintendent of public instruction who launched his gubernatorial campaign in 2023.

The Democrats in the race are talking to many of the same potential donors, Thurmond said, and most have the same question: “Is she going to run?” The only answer, Thurmond said, is an unsatisfying one: “We don’t know.”

Since leaving Washington in January, Harris has mostly stayed out of the public eye, settling back into her Brentwood home with her husband, Doug Emhoff, and talking to close friends and confidantes about what she should do next. She is weighing whether to leave politics, run for governor or run for president for a third time. She is expected to make a decision about the gubernatorial race by the end of summer.

The Democrats who are already running for governor lack Harris’ star power, and her entry could upend the race. But the former vice president would also face questions about her 107-day sprint to the White House, what she knew about President Biden’s decline and whether someone who has run unsuccessfully for president twice really wants to be California’s governor.

“She is looking closely where is the best place to put her energy and focus and her time,” said Debbie Mesloh, a longtime Harris ally.

The few public appearances Harris has made this year — meeting with firefighters in Altadena, attending a high school graduation in Compton and headlining a Democratic National Committee fundraiser in the Bay Area — have been fodder for those trying to read the tea leaves. What does it mean that Harris skipped the state Democratic Party convention? That Emhoff has taken a teaching job at USC?

Harris had originally planned to take a two-week vacation at the end of this month but has canceled her trip, according to someone familiar with her plans.

Harris has also been in New York, where she attended Broadway plays and the exclusive Met Gala; in San Francisco, where she dined with her niece Meena at the high-end Japanese restaurant Shoji; and in Los Angeles, where she has shopped for groceries at a 99 Ranch Market in Westwood and the Brentwood Farmers Market.

As the months have worn on, some gubernatorial campaigns have started to think that Harris’ victory feels like less of a foregone conclusion than if she’d announced in January after leaving office.

Former Los Angeles Mayor Antonio Villaraigosa, former Biden Cabinet secretary Xavier Becerra and former U.S. Rep. Katie Porter of Irvine have said that they will stay in the race no matter what.

Veteran state Senate leader Toni Atkins of San Diego said she is also staying in if Harris runs, saying in a statement that “while the vice president has her own path, our campaign is moving full speed ahead.”

Former state Controller Betty Yee said in an interview this week that even if Harris runs, she is staying in, too.

“No, no, no,” Yee said, of the possibility of seeking another statewide office. Being governor, she said, “is what I feel like I’ve prepared to do. I will be staying in the race and really leaning into my fiscal and financial background.”

Yee said when she talks to donors, they want to know two things: how California can push back against the Trump administration, and what she will do if Harris enters the race.

Dan Newman, a political strategist who’s worked for Newsom, Harris and several of the gubernatorial candidates, said that the race is at an odd inflection point, with candidates who “don’t know who their potential voters are, because they don’t know who they’re running against,” and some donors who are waiting — at least for now — to write big checks.

“They’ve got a good excuse to not give, because even if they are a big fan of a candidate who’s in the race now, they don’t know if the candidate will stay in the race,” Newman said. “Then there are others who don’t want to give to someone who might run against her.”

Eric Jaye, a political strategist who previously worked for Villaraigosa’s 2018 gubernatorial campaign and advised Newsom when he was mayor of San Francisco, said he’s hearing “frustration” from donors who are ready to see the race pick up speed.

“They’re not going to wait much longer,” Jaye said. “There are going to be donors who say, ‘We have to go. We’re not going to wait for you.’”

But even if Harris entered, that wouldn’t be a guarantee that donors would back her again, including those who are angry that she spent nearly $1.5 billion in campaign funds in her compressed campaign for the White House in 2024.

“The money is very, very upset with her,” said gubernatorial candidate Stephen Cloobeck, a businessman and Democratic donor who is running for California governor. “They’re my friends. I’m part of that money. Everyone is thoroughly reeling.”

The amount of money that candidates raise is one way to gauge their support — and prospects. That picture remains a little fuzzy, though, since gubernatorial candidates have until July 31 to report their fundraising hauls from the first half of the year.

The only candidate to release numbers so far is Becerra, who said he raised $2.4 million since entering the race in early April, including a $1.1-million transfer from his congressional campaign account. Becerra’s campaign has $2 million on hand, including the largest contributions allowed by law — $39,200 — from the politically connected Agua Caliente Band of Cahuilla Indians and Pechanga Band of Indians.

Campaigns are required to report contributions of $5,000 or more shortly after they receive them. Those figures don’t represent total fundraising, but can still show a campaign’s trajectory.

Three of the eight candidates have raised less than $100,000 this year in chunks of more than $5,000 at a time, state data show. Yee reported $71,900 and Thurmond, $32,500.

Lt. Gov. Eleni Kounalakis reported raising $70,000, including $5,000 from Google. Her campaign said Kounalakis, who has been raising money since entering the race in April 2023, has $9 million on hand.

“I want to be clear that I’m in this race to win,” Kounalakis said.

Villaraigosa, who entered the race last summer, has raised almost $1 million this year through large donations, data show. Atkins reported about $381,000 this year, and Cloobeck, about $132,000.

Porter, who entered the race in March, reported almost $475,000 in larger contributions, according to state data. She also transferred $942,000 from her U.S. Senate account to her gubernatorial account, according to federal filings made public Tuesday.