Illustration: Sam Wooley (Photos from Getty)

At 85, California Democrat Dianne Feinstein is the country’s oldest senator. To the disappointment of some on the left, she decided not to retire this year, saying she wants to keep the Senate seat she has held since 1992. With 26 years of wins under her belt, most people expected the election to be more a formality than a campaign; Republicans didn’t even bother running a real candidate against her in the primary.

Thanks to that, and California’s “jungle primary system”—by which the top two vote-getters regardless of party advance to the general ballot—Feinstein is now facing a formidable challenge in Kevin de León, a 51-year-old Democrat to her left, who, despite lacking her name recognition or war chest, has been eroding her considerable lead in the polls. Thanks to spending the last decade in state politics, most recently serving as president of the California Senate, de León even managed to seize the California Democratic Party’s endorsement.

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De León has been demanding for months that Feinstein face him in a debate, something she hasn’t done with an opponent in nearly two decades. Her campaign has said she is too busy with her responsibilities in Washington, D.C., where her seniority on the Judiciary and Intelligence Committees is key, particularly with the current confirmation hearings for Supreme Court nominee Brett Kavanaugh. But now, two months ahead of the election, she is facing a crisis of her own making that calls her years of experience in the Senate into question.

First the left was disappointed by her being “polite” to Kananaugh and expressing her frustration over the presence of protestors. Then things got crazier: The left had been looking for fodder to disqualify a candidate they consider unforgivably conservative, and Feinstein had a bombshell. In July, she had received a letter from a California professor who claimed to have been assaulted by Kavanaugh in the 1980s when they were both in high school. Christine Blasey Ford, who has since revealed her identity, initially asked that her story be kept confidential. Feinstein sat on the letter for over a month while Ford debated what she wanted done with the information, until news of the letter leaked last week, which prompted Feinstein to send the letter to the FBI.

Deciding what to do with the letter, given the accuser’s desire for confidentiality, certainly wasn’t an easy call. “It has always been Mrs. Ford’s decision whether to come forward publicly,” said Feinstein in a statement. “For any woman, sharing an experience involving sexual assault—particularly when it involves a politically connected man with influence, authority and power—is extraordinarily difficult.”

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Regardless, Feinstein’s failure to publicize the contents, or to share them confidentially with her fellow lawmakers, has proved controversial, leading to criticism from both the left and the right. De León’s campaign has been quick to jump on the news, putting out a press release about Feinstein’s “failure of leadership” and asking why Feinstein waited months to “hand this disqualifying document over to the federal authorities” while she “politely pantomimed her way through last week’s hearing without a single question about the content of Kavanaugh’s character.”

Since then, another Californian has come forward claiming to have offered damaging information about Kavanaugh’s relationship with a federal judge who resigned last year due to sexual harassment allegations, and for whom Kavanaugh had clerked in the 1990s. The California attorney says his letter to Feinstein about this was ignored.

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In an interview last week, de León put it simply: “Seniority means nothing if you don’t use it.”

While Kevin de León is far less well-known than Feinstein, he isn’t a complete newcomer to the national stage. The day after Donald Trump was elected, de León co-authored a public letter pledging to “lead the resistance” against the new president’s assault on California values, and he’s done so, getting two ambitious bills he authored on immigration and the environment passed: The first made California a “sanctuary state” and the second committed the state to use 100 percent renewable energy by 2045.

De León, who hit his term limits this year in the state legislature, says he decided to run against Feinstein last fall after she told an audience in San Francisco that “we have to have some patience” with Donald Trump. But it isn’t just Feinstein’s collegiality that de León has been attacking in his campaign. The son of a single immigrant mother and the first person in his family to graduate from high school, de León speaks the language of class warfare, and sees Feinstein as the enemy there.

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Kevin de León speaking in San Francisco
Photo: Kashmir Hill

During a series of speeches in San Francisco last week, de León called for fairer immigration policies and a strong government response to climate change, his signature issues. While speaking to a dozen people in front of a home in Bay View-Hunter’s Point, an area deemed San Francisco’s “most isolated neighborhood,” he argued that low-income people and communities of color should have just as much access to parks, clean air, and green technologies as wealthy elites, including those living “in Pacific Heights,” a dig at his opponent’s $20 million home in that particular neighborhood. (Feinstein is the second-richest person in the Senate, worth over $50 million.) De León, on the other hand, dropped out of UC-Santa Barbara after he lost his financial aid, and then cut his political teeth working as an organizer for immigrants, eventually running for office after California passed anti-immigrant legislation that convinced him immigrants needed a voice in the legislature.

De León has charisma and a compelling personal story, but remains impoverished compared to Feinstein when it comes not just to personal wealth, but to fundraising. He’s raised a twentieth of what she has; when the campaigns submitted their financial reports in June, Feinstein had $3.7 million cash on hand while de León had just $400,000. And it shows. A CEO from a green nonprofit who had attended the Bay View-Hunter’s Point event chatted with me before his speech and suggested his campaign needed to do more advertising. “I didn’t even know he was running for the Senate and I’m a fan,” she said.

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Just having a more liberal candidate opposing her seems to have moved Feinstein to the left a little. She announced this year that she has changed her long-time stance on the death penalty to oppose it and now supports medical marijuana, bringing her more in line with the majority of her state’s voters.

Feinstein is an institution in California, with roots that go back to taking over as San Francisco’s mayor in 1978 after the sitting mayor was assassinated. She has been in the Senate since before many California voters were even born. She’s been around forever. In November, voters will decide whether or not forever is too long a time to be around.

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De León is the perfect candidate on paper to challenge Feinstein, and is widely seen as more representative of the future of the Democratic Party in California than is the centrist Feinstein, but he, like any politician, has made troubling decisions in the past. When I asked him about his stance on technology and privacy, he signaled an intent to stand with the powerful players. “Technology has helped California grow as a state,” he said. “We haven’t had a strong voice in Washington that stands up for technological interests.”

Last year, for example, de León allowed a bill to die that would have given Californians privacy from their Internet service providers, who have traditionally been significant donors to him. One of the bill’s biggest opponents, AT&T, had helped fund a lavish $50,000 celebration for De León at Walt Disney Concert Hall in 2014 when he became the California Senate president.

De León, further, has his own problems around women whose harassment claims were ignored that could come into play in November. He lives in Los Angeles, the district he represents, but when in the state capital of Sacramento each week for work, he was, until last year, roommates with now-former state Senator Tony Mendoza, who resigned last fall after being accused of sexual harassment toward women colleagues. Mendoza had pressured young staffers to come to his hotel room and to his home, and fired employees who complained about his inappropriate behavior. When this became public, De León quickly moved out of Mendoza’s home and, as Senate president pro tempore, established a new independent investigative body to respond to allegations of harassment. De León has claimed he was completely unaware of Mendoza’s behavior and when I asked him whether he’d become aware of any blindspots as a result of the episode, he told me he doesn’t think he has any (as well as clarifying that Mendoza was more his landlord than his roommate).

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“I didn’t witness any inappropriate behavior. The only women I witnessed come to the house were his wife and his daughters,” he told me. “This isn’t a state capital issue in Sacramento. It’s a societal issue that permeates [many industries and places.] If anything, what we’ve done is take a system I inherited and made the reforms to make it more responsive to any type of allegation of harassment.”

Liberal candidates across the U.S., from Alexandria Ocasio-Cortez in New York to Andrew Gillum in Florida, have been displacing less liberal Democrats this year, so De León could benefit if the trend continues in the Golden State. But longtime California political consultant Darry Sragow, who worked on Feinstein’s first campaign in 1990, thinks that strategy could backfire.

“In a race with no Republican candidate, moving to the left is not a recipe for winning,” said Sragow. “I think it’s his best shot, but that he’s doing it for the future. Being a state senator from Los Angeles isn’t a recipe for being known state-wide. This is a state of 40 million people and Californians don’t pay attention to politics. So just getting statewide name recognition and being seen as a progressive and a fighter is all upside for him.”

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Most political observers agree that de León’s run is a long shot. It’s unclear whether California voters will actually care about Feinstein’s missteps in the Kavanaugh hearing or the fact that she’ll be 91 at the end of her next Senate term. In theory, de León—a relatively young Latino leader with an appreciation for economic and ethnic diversity, fear about the environmental future of the planet, a desire for Medicare for all, and a deep-seated hate of Trump—is an ideal person to inherit the Senate mantle. He’s running on idealism, which is easy to theoretically cheer. In reality, Feinstein will probably win again, because she has a lot more money, a lot more name recognition, and California voters have had over two decades to get to know her. They know exactly what they are going to get, or perhaps don’t care. De León has a golden California shine. but voters don’t know who he is yet and there isn’t enough time to get to know him before November 6. Unless there is.

*Updated with link to most recent poll on the race