Running Uphill: The Challenge of Unseating Dianne Feinstein

Supporters of Senator Dianne Feinstein and of Kevin de León, the State Senate leader, at the California Democratic Party convention in San Diego in February.

OXNARD, Calif. — Kevin de León is one of the most prominent Democratic figures in the nation’s most Democratic state. He has drawn national attention from the Democratic left for a spirited challenge to Senator Dianne Feinstein and for the aggressive legislative challenges to President Trump’s policies advanced by the State Senate under his leadership.

But these days, Mr. de León is struggling for a toehold as he tries to negotiate the fraught and complicated terrain of trying to topple someone widely seen as a California institution. At 84, Ms. Feinstein is a five-term senator who began her political career as a member of the San Francisco Board of Supervisors in 1969, when Mr. de León was just 3 years old.

Mr. de León, 51, represents what many party members see as one of the leading faces of the next generation of California Democratic leadership amid calls for Ms. Feinstein to step aside to make room for the next class of leaders.

But Mr. de León’s struggles suggest that this moment of transition remains a work in progress. He would seem to have the right political makeup to lead the party to its next chapter. He is more liberal than Ms. Feinstein at a time when the left is on the rise. He is Latino in a state where the power of Latino voters continues to grow. And he is coming off almost four years as president of the Senate, giving him a platform to present himself as one of the state’s most aggressive leaders in opposing Mr. Trump.

Yet he is running against a powerful remnant of California’s old guard who enjoys strong historical, cultural and sentimental ties to many Democrats who have followed Ms. Feinstein’s career over the decades. Mr. de León’s run is exposing the challenges for a candidate who at any other time — or against another opponent — would seem to be a potentially powerful competitor.

Mr. de León is not, for the most part, facing questions on his record; rather, in the view of many of Ms. Feinstein’s supporters, she is a highly successful senator and foil to Mr. Trump, especially on national security issues, and there is simply no reason for her to go.

Ms. Feinstein’s hometown paper, The San Francisco Chronicle, in endorsing her, referred to Mr. de León as “the Young Turk.” In many ways, Mr. de León — who was blocked from seeking re-election to the Senate because of term limits — may end up being the right person but at the wrong time.

“I am not delusional,” he said over an açaí bowl at a diner in San Diego. “Listen, I am not naïve to the fact that people are not shouting my name all over the state of California. What we’ve identified is after 25 years of unchallenged incumbency, people in California want a change. And a new voice representing them. I want to be that voice.”

But, he said, “It’s a tough race.”

Mr. de León did have a moment of triumph, as it were, a few months ago when he drew 54 percent of the delegate vote at the state Democratic convention in San Diego. That was enough to block Ms. Feinstein from winning the party’s endorsement (she drew 37 percent) but shy of the 60 percent needed to secure it for himself.

Since then, there is little sign that any electricity generated from the convention floor has powered him to greater political success. The other day, he sat down for 90 minutes with the editorial board of The Chronicle making a case for its support; less than 24 hours after he left, the paper posted its endorsement of Ms. Feinstein. A few weeks later, another indignity — President Barack Obama, who has almost without exception stayed out of nonlocal Democratic primaries since leaving the White House, weighed in with a rare endorsement. He backed Ms. Feinstein.

Polls, while of questionable accuracy given the mostly unknown field of candidates from both parties, suggest Mr. de León is struggling to win one of the top two spots in the June 5 nonpartisan primary. Ms. Feinstein has $10.4 million in the bank, including $5 million she lent her campaign, compared with $672,000 for Mr. de León, as of March 31.

So it was that Mr. de León could be found one recent Saturday driving himself around in his blue Chevy Volt from rally to picnic, singing along to Morrissey on the radio, in a one-car campaign caravan that took him from downtown Los Angeles to Thousand Oaks to Oxnard.

Mr. de León has earned applause from some Democrats for leading the Senate as it challenged Mr. Trump.

But Mr. de León’s tenure was also marked by a flood of sexual harassment cases involving lawmakers and legislative aides. Nearly 200 women signed a letter complaining of rampant sexual misconduct in Sacramento, and the disclosures forced Mr. de León and other legislative leaders to revamp disciplinary procedures.

He has hammered Ms. Feinstein for showing a willingness to work with Mr. Trump and he has taken positions on issues — military intervention, health care, tax cuts, among them — that stand in contrast to the more moderate and measured senator.

More pointedly, he made a point of contrasting his background with Ms. Feinstein, portraying her as the wealthy doyenne of San Francisco Democratic politics and himself as the working-class son of a San Diego barrio seeking to become this state’s first Latino senator. Mr. de León recently took a reporter on a tour of Logan Heights, the San Diego neighborhood where he grew up, and lingered at a single-room apartment where he shared a bed with his single mother who worked as a housekeeper. The tour was memorialized by an aide for a Facebook Live feed.

“This is Logan Heights — and then there is Pacific Heights,” he said when he got back to his car, a reference to the neighborhood in San Francisco where the senator now lives. “They are two different planets.”

“I try to deal with the poverty gap — to do policies for all of us, rather than only for the wealthy,” he said. “She votes for two wars without a way to finance the wars, votes for a Republican tax cut that as a billionaire, she benefits greatly from. That is a gross abuse of power.”

It is a measure of Mr. de León’s standing in the polls — and the fact that as of now, at least, he is not viewed as a real threat to the senator — that Ms. Feinstein has while campaigning avoided engaging Mr. de León.

Her campaign manager, Jeff Millman, defended her performance. “Rather than responding to political cheap shots, Senator Feinstein is responding to the everyday needs of Californians by opposing Trump’s tax cuts for the wealthy, his attempts to repeal Obamacare and his attacks on Dreamers,” he said.

There is clearly an audience who share Mr. de León’s view that it is time for Ms. Feinstein to step aside.

“You shouldn’t have to push someone not to run,” Ryan Skolnick, 25, a speech coach from Simi Valley, told Mr. de León as he moved through a crowd of supporters at a restaurant in Oxnard.

R. L. Miller, the chairwoman of the environmental caucus of the California Democratic Party, nodded vigorously when asked if she thought Ms. Feinstein should retire. “Oh my gosh — where do I start?” she said. “We can upgrade. She’s reliable. But he has the heart of an activist — she does not.”

Graciela Soliz Ventura, 68, a retired schoolteacher, said that she had long been a “big supporter” of Ms. Feinstein, but that the senator’s time had passed.

“She’s not listening to California and our values,” she said. “Enough is enough.”

Still, Ms. Feinstein is widely respected, if not necessarily revered, which complicates Mr. de León’s task. In interviews, he repeatedly said he is not suggesting she is too old to return to Washington, but rather that she is ideologically out of step.

It is not an easy case to make.

“You are disrupting the status quo,” he said. “You are challenging the establishment authority that has been out of touch with California voters. Times have changed.”

Mr. de León suggests that Ms. Feinstein is treated deferentially, by the press and the public, because of her stature. “She gets passes,” he said. “She constantly gets passes.”

Mr. de León said he decided to challenge Ms. Feinstein after she called for “patience” with Mr. Trump.

“As Democrats we will never be fooled into believing that if we are patient enough, that Donald Trump could be a good president,” he said to applause from a group of voters ambling under the sun on a patio at a Mexican restaurant in Oxnard. “This is not a time to be polite or patient.”

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