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This Is How Trump Will Try to Take Down Kamala Harris

Are the Democrats ready for grotesque attacks about the senator’s ex-boyfriend Willie Brown?

Samuel Corum/Getty Images

Biden’s search for a running mate is getting messier by the day. Over the last few elections, vice presidential candidates have been announced just days before the party conventions, so the pace of Biden’s selection process seems to be well within, if not ahead of, precedent. Still, the squabbling over the pick this time around has been highly visible and fraught. We can credit that partially to petty intra-party politics. But there’s also a sense among Democrats that Biden’s choice could be pivotal, given his age and the likelihood that Trump will turn attention to the other half of the ticket if his attacks on Biden continue to fail.

The conservative press has spent the past few weeks dredging up material to deepen Democratic anxieties. Representative Karen Bass, a fast-rising contender, has had to explain past remarks on Cuba and the Church of Scientology. Former national security adviser Susan Rice’s role in the Benghazi pseudo-scandal has been resurfaced. Meanwhile, Senator Kamala Harris remains a top-tier candidate, if not the frontrunner, for reasons that have been obvious since the selection process began: She’s conventionally experienced, she’s built a large national profile and political network, and she would satisfy Democratic voters and leaders who want Biden to pick a woman of color. This is not to say that she’s escaped recent scrutiny. Her lack of remorse over the criticisms she leveled at Biden during the primary has reportedly convinced some in the campaign that she’s an inauthentic striver more interested in succeeding Biden than supporting him. Harris’s defenders have countered that slights against her ambition reflect a sexist double standard.

It’s doubtful that this conversation would be electorally important if Harris were chosen. Voters are used to seeing the critics of primary candidates reverse themselves once those candidates are nominated. As a Biden-Harris campaign would surely point out, the very same thing happened with Mike Pence in 2016. It also seems unlikely that the criticisms Harris received from the left during the primaries will matter much either; Trump, invested in the message that Democrats are dangerously soft on crime, won’t have much of an incentive to highlight her prosecutorial record.

But there is one thing about Harris’s past that Trump and the right are almost certain to focus on if she’s chosen. Briefly in the mid-1990s, Harris, then a deputy district attorney in California’s Alameda County, dated future San Francisco Mayor Willie Brown, who was then speaker of the state assembly and a powerful figure in state politics. Brown was married, but he had by then been estranged from his wife for over a decade; his other relationships were frequently reported and commented on in the local press. While they were dating, Brown gave Harris a car and appointed her to the California Unemployment Insurance Appeals Board and the California Medical Assistance Commission, where she earned more than $400,000 over the course of five years.

Harris spent her early years in politics defending what she’d accomplished in those positions—“whether you agree or disagree with the system,” she said in 2003, “I did the work”—and tried to distance herself from Brown, who has been investigated multiple times by the FBI. That effort basically succeeded⁠, despite Brown’s attempts to insert himself into her career and affairs. In January 2019, less than a week after Harris launched her presidential campaign, Brown penned a short piece on their relationship for The San Francisco Chronicle. He wrote, “Yes, I may have influenced her career by appointing her to two state commissions when I was Assembly speaker. And I certainly helped with her first race for district attorney in San Francisco. I have also helped the careers of House Speaker Nancy Pelosi, Gov. Gavin Newsom, Sen. Dianne Feinstein and a host of other politicians. The difference is that Harris is the only one who, after I helped her, sent word that I would be indicted if I ‘so much as jaywalked’ while she was D.A.”

In other words, Harris’s appointments were defensible because they’d been made within a very large and influential political machine and because Harris would go on to promise, almost a decade later, to keep an eye on Brown as district attorney.

Ultimately, Brown never became a problem for Harris’s presidential campaign, and interest in him faded even within conservative media, which latched onto the issue for a moment when Harris was announced. Curiously, the right is keeping mostly quiet about him, even now as Harris returns to the spotlight as a vice presidential contender. On his show Monday night, Tucker Carlson opened with a segment on the veepstakes in which he argued that Biden’s running mate will be the “actual Democratic nominee” and “the person who will run the government if Biden wins in November.” Before turning to Susan Rice, whom he framed as the frontrunner, Carlson singled out Harris, Bass, and former Georgia gubernatorial candidate Stacey Abrams for criticism. “In a normal year, no mainstream candidate would consider any of these people,” he said. “All of them would be disqualified without debate.” He went on to list their faults: “Karen Bass is a lunatic Fidel Castro acolyte who praised Scientology and once belonged to an armed revolutionary group. She’s out. Stacey Abrams is so delusional she thinks she’s the governor of Georgia—and by the way, she’s essentially unemployed. In one of her last regular jobs, she wrote bad porn novels—for real. Kamala Harris, meanwhile, is so transparently transactional, even Democratic primary voters, who have a strong stomach, found her repulsive. Pretty much no one who knows Kamala Harris likes her.”

One of these critiques is not like the others: The dirt on Bass and Abrams was followed by a hit on Harris’s personality and ambition. It would be truly odd if researchers who went to the trouble of bringing up a B or C list contender’s writing career managed to miss Willie Brown. But he wasn’t mentioned—not on Carlson’s Monday show, not in Sean Hannity’s remarks on Harris the same night, and not in Carlson’s extended riff on Harris last week.

This may well be a simple oversight—a stuck gear in the typically well-oiled conservative noise machine. But there are two other possibilities. It’s plausible that conservative operatives just don’t think they can use the Brown material. It’s also plausible that they’re waiting for Harris’s selection to “discover” the story and use it against her. It shouldn’t be forgotten that one of President Trump’s favorite subjects of late has been the governance of Democratic cities. In fact, he and the rest of the right have been particularly fixated on San Francisco, which the conservative press regularly depicts as a lawless progressive dystopia. Moreover, it’s hard to imagine a more irresistible line of attack for Trump: He is obviously comfortable deploying both crude sexism and racist innuendo for his own ends. And there’s no reason to believe corruption in his administration would render him any less willing to make patronage an issue. After all, the assault accusations leveled against him in 2016 didn’t dissuade him from resurrecting the allegations against Bill Clinton. Rather, they encouraged him to do it.

But the inevitability of a discourse about Brown if Harris is selected has less to do with Trump’s particular traits than the fundamental habits and strategies of Republican mudslinging. Figures like Brown have been the subject of right-wing messaging and attack ads for generations. Whether those attacks will actually work on anyone outside the Republican base in this particular election is an open question. For one, Trump’s bigotry and culture war offensives have alienated moderate and suburban voters over the course of his presidency—doubling down on them against Harris or anyone else could very well backfire. And voters of all stripes clearly have more important things on their minds right now; the coronavirus pandemic might drown out Republican attempts to drum up scandal as thoroughly as the financial crisis helped drown out messaging about Tony Rezko, Jeremiah Wright, and all the other opposition research against Barack Obama in 2008. But as the effort to have us imagine Karen Bass as an armed revolutionary demonstrates, it’s likely that a flailing Trump campaign will try to throw the sink at Harris or whoever the running mate is anyway.