SANTA ANA, Calif.—Fourteen people and three rescue cats were awaiting Kevin de León when he pulled up to a PetSmart and stepped inside through drizzling rain. In his briefing folder, an aide had included a note titled, “Cat puns you can use, if you’re feeling festive!” De León hit nearly all of them. “Meow is the time,” he told the members of Kitty Devore Rescue, describing himself as an “alley cat.” Grateful for de León’s attention, a woman beamed back at him, “Someone knows our name!”

It had been two weeks since de León impressed a crowd on a more brightly lit stage. In a coup at the California Democratic Party’s annual convention last month, de León—until Wednesday the Democratic leader of California’s state Senate—deprived Dianne Feinstein of her own party’s endorsement by outpolling the state’s senior senator by 17 percentage points in the delegate vote. Although de León fell short of the 60 percent threshold necessary to claim the party’s backing himself, he embarrassed Feinstein and put a California institution on her heels.

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For de León and his supporters, the convention marked a turning point not only in his quixotic campaign to unseat Feinstein, but also in a generational struggle among Democrats in the nation’s most populous state. For decades, Feinstein and her centrist brand of politics have appeared as immovable as House Minority Leader Nancy Pelosi and California’s fourth-term governor, Jerry Brown. For once, a restless, more progressive class of Democrats had unsteadied the establishment. De León skewers Feinstein for her moderation and depicts her as unfit to battle President Donald Trump. He is also testing the muscle of the nation’s newly emboldened left.

“Time’s up!” de León’s supporters chanted as Feinstein left the convention stage. Tom Steyer, the billionaire environmentalist and Democratic megadonor who once considered challenging Feinstein himself, described the contest on MSNBC as “incrementalism versus visionary thinking in the Democratic Party.”

Yet if de León’s success at the convention showed the power of the Democratic Party’s left flank, the days that followed have laid bare its limitations. A champion of progressive causes in Sacramento, de León is largely unknown statewide. Typical of state lawmakers, despite his outsize influence crafting state law, de León’s plight outside the capital is jarring anonymity. Calls he places to prospective donors go to voicemail, and the checks he does receive are small.

Watching de León campaigning between displays of DentaStix and turkey-and-sweet-potato dog food, state Sen. Josh Newman, a colleague of de León and a representative from the area, turned and said, “What is it, 9 in the morning on a rainy Saturday? And he’s out talking to cat people.” Newman took that as a positive sign. It wasn’t long before the 2008 presidential election, Newman said, that “Barack Obama was speaking to crowds of, like, eight.”

Leaving the PetSmart, de León climbed into the passenger seat of a staffer’s Honda Odyssey for two more campaign stops and 12 hours on the road.

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The odds against de León are so overwhelming that when Sara Nichols, a retired environmental attorney, begged him to challenge Feinstein at a fundraiser in Los Angeles a year ago, she recalled him telling her: “It’s a suicide mission. I’m not going to do it.” Now, heading north from Santa Ana to Santa Barbara on California’s coastal Highway 101, de León put it this way: “Hard as hell? Yes!” before adding, “But things have always been hard for me.”

De León, 51, says he spent part of his childhood living with his mother and sisters in a basement with a bathroom up a flight of stairs outside. He would ride the bus with his immigrant mother from San Diego’s Logan Heights to her jobs cleaning houses in wealthier neighborhoods. He was the first member of his family to graduate from high school and the first to attend college, at the University of California, Santa Barbara. He then became the first to flunk out. “I was embarrassed to go back home,” he said. “I didn’t know what I was going to tell my mom.”

So de León stayed in Santa Barbara, going to work for a nonprofit that taught English to immigrants in preparation for their citizenship exams. He bounced checks at a local restaurant and slept on a floor in his office, he said, showering with water that he heated on a hot plate.

“I was completely oblivious as to what he was doing, and I was very confused by it,” says San Jose Vice Mayor Magdalena Carrasco, de León’s former girlfriend and the mother of his now-grown daughter. “Who does that? You’re supposed to be studying, and you’re supposed to be having fun, and you’re supposed to be hanging out with the boys.”

Instead, said Carrasco, who remains close to de León, “He was hanging out with all the older women who were cleaning the dorms, and he was teaching them English, and he was helping them get ready for their U.S. citizenship classes.”

De León went on to work as a labor organizer, and in 1994 he helped organize a massive protest against Proposition 187—the voter initiative, later overturned by the courts, that barred undocumented immigrants from receiving certain public services. Years later, he graduated with honors from Pitzer College in Claremont. And after defeating a granddaughter of the late labor leader Cesar Chavez to win a seat in the California State Assembly in 2006, he went on to amass a string of legislative victories on liberal causes from climate change to gun control to wage and labor law.

But it was the election of Trump that gave de León a platform from which to run for higher office, drawing national media attention—if not widespread name recognition—as a principal combatant in California’s Democratic resistance to the president. After Trump’s election, de León pressed for state money to provide legal assistance to immigrants facing deportation, and he introduced California’s so-called sanctuary state legislation, which limits local law enforcement officials’ ability to cooperate with federal immigration authorities. The headlines kept coming this year, when de León responded to the Republican tax overhaul in Washington by introducing state legislation seeking to give California taxpayers an end run around new limits on the state and local income tax deduction.

After spending much of the past year passing—and now defending—the “sanctuary state” bill, de León says he recoiled when Feinstein suggested at a public forum last year that Trump, given time, could become a “good president.”

“That was a very powerful statement to make that violated the values I abide,” he said, pointing to tracts of strawberry fields where he once recruited English learners for his classes outside of Santa Barbara. “You can’t ask Dreamers to have patience. You can’t ask a hard-working immigrant mother who’s fearful of being detained and deported to have patience, who’s been here for decades to have patience. You can’t ask someone who is a beneficiary of health care to have patience. You can’t ask those who suffer disproportionately from climate change and the harmful effects of toxic pollution to have patience. That comment, I believe, runs strongly contrary to the values of who we are as a great state. And that’s when I actually started thinking about it for the first time.”

Now, sprinting across the state from one small crowd to another, de León paints Feinstein as a creature of Washington out of touch with California’s younger, more progressive electorate. He criticizes her support for the Iraq War and the PATRIOT Act, and for her skeptical view of single-payer health care. And though he scrupulously avoids mentioning her age directly—at 84, she is the Senate’s oldest member—his frequent praise for her “decades of service” appears designed to make the point.

“I do believe this is a campaign of vastly different values,” de León says. “You know, I respect her service to California and the nation, but the state has changed dramatically in the past quarter-century, and it requires, I believe, a new voice that carries the values of California today, not yesterday.”

De León’s politics—and his circumstances—diverge sharply from those of Feinstein, one of the wealthiest members of Congress. He does not own a house, and his investments include stocks worth no more than $40,000, according to financial disclosures filed this month. In the home he rents in Mount Washington, in northeast Los Angeles, two hammocks hang across the room from a chess board and a weight bench that he uses when he finds time. His favorite suit has holes in its lining. For a “bad stretch” during the campaign, de León says, he was eating at In-N-Out Burger every night.

Twelve years after de León defeated her in his first legislative campaign, Christine Chavez, Cesar Chavez’s granddaughter, says she likely will vote for him.

“I just think he really sticks his neck out there when not so many people are willing to be as bold as he is, when he’s talking about protecting the rights of undocumented immigrants, protecting Dreamers,” she told me. However, she says, “You need money to run ads on TV, and you need money to get your message out there.”

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While De León’s thumping of Feinstein at the state party convention startled many in Washington, it was not unexpected by most political observers in California. Feinstein has long maintained a tenuous relationship with the party’s most progressive activists, and she lost the state party endorsement once before, to John Van de Kamp, when she ran for California governor in 1990.

But state party conventions reflect a more fervent class of Democrats than exists within the party statewide. In that broader landscape, Feinstein remains stalwart, outpolling de León 42 percent to 16 percent among likely California voters, according to a poll released Wednesday by the Public Policy Institute of California. As one woman put it to de León at an event in Santa Barbara, to vote against Feinstein—after marking ballots for her for decades—seems “counterintuitive.”

De León has secured endorsements from two politically powerful unions, the Service Employees International Union and the California Nurses Association, and he may benefit from getting to run against Feinstein twice: Because of California’s unusual top-two primary rules, he and Feinstein are each likely to advance from the June primary to face each other a second time, in a runoff in November. But de León’s fundraising to date is concerning not only to de León’s supporters, but also to the candidate himself. Feinstein held close to $10 million in cash on hand at the end of last year, while de León reported raising just $500,000.

Told by an aide following an event in Santa Barbara that a supporter had cut a $50 check, de León’s eyes grew wide and he responded enthusiastically, “Are you serious?”

When de León made a brief round of fundraising calls on the road to his next appearance, no one answered. “Therein lies the challenge,” he said. “When I talk to folks, they say ‘I’m voting for you.’ But I don’t have the money to get the message out.”

When I asked him why his prospective donors aren’t answering his calls, he smiled and said, “Because they love me, but they don’t know if I can win.”

Fabian Núñez, California’s former Assembly speaker and a childhood friend of de León, says it has frustrated de León that, after serving as president of the state Senate, “still people in California don’t know who he is.”

“That’s a real frustration,” Núñez says. “I think he expected more people would know him.” On the other hand, Núñez says, “he’s banging the drums so loudly now, they are starting to take notice.” He added, “If people knew him—if he’s able to get out there and build that contrast between him and her—then I think he can win.”

De León has proved adept—and tireless—at cultivating the news media. He rises early for cable TV hits, returns reporters’ telephone calls and is a reliable fount of rhetoric lambasting Trump. On the evening this month that Attorney General Jeff Sessions announced his lawsuit against California’s “sanctuary state” legislation, de León fielded calls while collecting Carrasco’s son from a track event. In the middle of talking about the Department of Justice’s record in court against the state (“I like our odds”), de León interrupted himself as he steered his Toyota Camry around a neighborhood in San Jose. “Where is this kid?” he said.

For her part, Feinstein has been largely dismissive of de León. De León cannot run for reelection to his current seat because of term limits, and Feinstein’s longtime campaign adviser, Bill Carrick, said of de León’s U.S. Senate candidacy, “Oh, please … He’s a termed-out politician looking for a gig.” Of all the races he could have entered—for governor or lieutenant governor or any other statewide office—Carrick said, “This is probably the biggest challenge he could have taken on.”

Even so, Feinstein’s allies have started to chip away at de León. Christine Pelosi, the chairwoman of the California Democratic Party’s Women’s Caucus and the daughter of the House minority leader, regularly criticizes him for his handling of a sexual harassment scandal in the state legislature that has led to the resignation of two Assembly members and one senator, Tony Mendoza, in whose house de León previously stayed while working in Sacramento. Pelosi has said legislative leaders should have done more to investigate complaints and shield victims from reprisals, while de León said he was “really proud” about procedural changes the legislature made to address sexual harassment in recent months.

De León says the scandal won’t present a political problem for his Senate run. “They’ve politicized it,” he says. “We understand what they’re going to do.”

If his campaign takes flight, de León’s critics are likely to grow louder. Days after de León’s convention performance, former state Treasurer Phil Angelides, labor icon Dolores Huerta and a handful of other Feinstein supporters formed a super PAC to back Feinstein in her reelection bid. Angelides, a former state party chairman, advised Democrats to focus instead on “taking back the House and the Senate.”

Still, Angelides acknowledged the winds that de León is hoping to ride. “There’s a tremendous amount of restlessness in the country,” he said. “There’s a lot of tumult. Our politics right now are in a sense turned upside down.”

If de León falls short, he could run for mayor of Los Angeles or for another statewide office. He says he’ll “cross that bridge” if he has to in November. But on this day, he had come to San Luis Obispo, where he stood on a stage with red, white and blue bunting, and looked down at a crowd of about 100 people inside a community hall. The city’s mayor, Heidi Harmon, introduced de León as the “next United States senator from California and professional thorn in the side of the federal government.” People were cheering, just like at the convention.

Leaving town for the long drive back to Los Angeles, de León turned up Morrissey and sang along, tapping his phone on his knee, “The more you ignore me, the closer I get.” He was yawning, but he offered to drive.

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