They know California is littered with rich people who thought their infinite wealth and wisdom in the private sector would carry over into electoral politics — only to be soundly rejected by the electorate for the most powerful offices. Sparing no penny, Bloomberg is the latest out to prove himself the exception — in large part by leading with his dozen years as mayor, his philanthropy and holding out a list of liberal accomplishments that portray him as a self-made slayer of Big Oil, Big Tobacco and the National Rifle Association.

His push comes as he takes incoming from the party’s liberal flank, led by Elizabeth Warren and Bernie Sanders. Bloomberg’s bet hinges on none of his opponents consolidating support and building unstoppable momentum in the first four states.

But nowhere more than in California is his run turning the presidential landscape into a giant political science experiment that tests how an aging ex-Republican known for his withdrawn campaigning style — and led by a seasoned band of political assassins — will fare. A multicandidate primary presents opportunities for Bloomberg to pick off delegates: Public polling shows a strong majority of Democrats in the state prefer elevating a nominee who could beat Donald Trump to picking a candidate whose policy views align more closely to theirs.

“It’s hard to bet against someone who has been as successful as he has in his life,” said former California Gov. Gray Davis, who vanquished several wealthy opponents as he climbed the ranks of state office. Davis lauded Bloomberg as a “fighter,” mentioning their past work together on gun control and redistricting. “I kid my friends. I said, ‘There are two billionaires in the race—and Trump is not one of them,’” Davis said, pointing to Bloomberg and liberal ex-hedge fund manager Tom Steyer, the climate and impeachment activist from San Francisco who is also running.

But Davis warned that Bloomberg will need a sizable retail component if he’s to shatter deeply ingrained resistance to candidates that parachute in and spend big. “What people still want, if they can, is to touch you, connect with you, and if they can’t connect with you personally, to see someone on television [news reports] with you at a coffee shop or barber shop or veterans hall that they can relate to.”

For now, Bloomberg’s three terms as mayor and his work personally funding organizations and individuals with connections to the state have opened up platforms unavailable to his rivals. He scored a rare public sit-down in San Francisco last week with Jerry Brown, the four-term former governor who remains one of the most popular figures in the state, to chat about climate change. The pair had appeared together before, including at climate talks in Germany, and while Brown didn’t offer his endorsement, he lauded Bloomberg’s stewardship of New York as “very good.”

“I believe he is not to be discounted,” said Steve Westly, the former state controller who raised more than half a million dollars for Barack Obama during each of his two campaigns. “The narrative of Warren and Sanders — ‘it’s just another billionaire trying to buy his way in’ — that doesn’t hold water. He’s a three-time mayor of New York. It’s one of the most diverse demographic areas on the planet. He was one of the best mayors in the country. Do not discount him.”

Whether Bloomberg can overcome a wealth curse whose largest exception was Arnold Schwarzenegger in a recall election is another question entirely.

California has a rich history of rejecting well-heeled candidates — so much so that its veteran class of operatives all have a pithy soundbite at the ready about the carcasses of millionaire candidates left to rot on the shoulders of freeways. They point to former eBay CEO Meg Whitman, whom Bloomberg campaigned for against Brown in 2010, and the more than $140 million of her own fortune that the Republican candidate blew through in her failed bid for governor; former Hewlett-Packard CEO and 2016 Republican presidential candidate Carly Fiorina; former GOP congressman and banker Michael Huffington; and airline and hotel executive Al Checchi, a Democrat who ran against Davis. They all spent millions of their own money before going down in defeat.

There are commonalities to the wealthy outsider approaches: Whitman, the business exec, shipped hundreds of thousands of copies of her 48-page policy plans to voters, while Checchi distributed his 90-page “Checchi Plan” that promised sweeping changes to education policy.

Now, as he bombards the state with nearly $15 million in TV ads, Bloomberg is touting his background along with his fights against coal plants, tobacco companies and gun-makers. He’s grown his support modestly to the mid-single digits in polls, but the more troubling aspect at the onset is his negative image with likely Democratic voters.

“There’s just not an appetite for self-funding billionaires in California,” said Doug Herman, a Democratic strategist in Los Angeles.

“Californians approach things differently,” he added. “That’s what attracted people to settle out here. It’s what attracted people to leave the East Coast. What works in the East doesn’t work here.”

Buzz for Bloomberg’s candidacy is still being surpassed by the current frontrunners, given his late start and strategy to skip the debates and first four states. “We all obviously have seen his TV ads. But it’s just not been a topic of conversation,” said Wendy Greuel, a former L.A. city controller who has met with several of the presidential candidates.

“Everyone is scratching their head and clearly looking at who can beat Trump,” she said. “Everyone is looking to see how people do in Iowa and New Hampshire.”

Others who at the start of the year were touting the virtues of a Bloomberg run are now cycling though other candidates.

Bill Bloomfield, a Democratic donor who challenged former California Rep. Henry Waxman as an independent in 2012, said he has no doubt Bloomberg would “smash Trump” in a head-to-head matchup. But as Bloomfield watched Pete Buttigieg’s rise, he said the young mayor developed a personal connection that will be hard for Bloomberg to match: “He has a calming mannerism talking from huge intelligence. It feels like you’re in the living room with him with no press around.”

Of Bloomberg, Bloomfield said: “I think he’s missed his time.”

Bloomberg’s campaign points out he’s just getting started. His national team has brought on its first slate of hires, including operatives that worked on House races across the state in the midterm elections. They’ve informally consulted with some of the state’s best-known strategists, testing out theories of where to campaign and probing for more plugged-in senior talent to head up regions.

Bloomberg aides insist he’ll be visible beyond the TV airwaves. They are teasing frequent trips with elected officials who can vouch for him, and a focus on his record rather than “100-page plans” that tripped up past wealthy campaigners in the state. They’re also vowing promising that their operation will extend to far-flung areas — from the Central Valley to Orange County to the Inland Empire — that were “frequently overlooked by presidential campaigns that parachute in the last two weeks,” a Bloomberg official said.

During his first visit as a presidential candidate last week, Bloomberg worked to expand his appeal by rolling out endorsements from the mayors of San Jose and Stockton, cities that span the state’s economic and ethnic diversity. He’s chatted with Los Angeles Mayor Eric Garcetti, a 2020 free agent being courted by virtually the entire field.

“He’s happy to welcome him to L.A. and provide any goodwill and advice,” Garcetti spokesman Yusef Robb told POLITICO.

Former San Francisco Mayor Willie Brown, who huddled with Bloomberg after the climate event in the city, said Bloomberg spent a lot of time talking with “average folks” in the room before meandering over to chat with him. “The ego was not at all at play on this one,” Brown said. “I really did out-ego him.”

They talked mostly about Bloomberg’s efforts to maintain Nancy Pelosi’s majority in the House, his funding for programs like Stacey Abrams’ voter rights group and whether any of the Democrats can beat Trump. Brown, the former longtime speaker of the state Assembly, said he came away impressed with Bloomberg’s focus on down-ticket party building and his style. But Brown stopped short of predicting of how Bloomberg would play with Californians.

“I love the fact that this is the one really rich guy that never ever apologizes for his money,” he said. “There’s no bullshit.”

Maggie Severns and Carla Marinucci contributed to this report.