SAN FRANCISCO—Before a campaign forum that would help to define her nascent political career, Kamala Harris, then a 38-year-old prosecutor, was bracing for questions about an uncomfortable topic: her relationship with the mayor of San Francisco, Willie Brown.

Harris’ consultant, Jim Stearns, had warned his candidate that her opponents would dredge up her ties to Brown, and the moment arrived at a church in the city’s gentrifying Noe Valley neighborhood. The race for San Francisco district attorney was still in its infancy, and Harris, who had never before run for public office, was polling in single digits. But she had an uncommon touch for fundraising and a biography that appealed to women and nonwhite voters. Her opponents took her seriously, but they also saw a weakness that could hobble her political ambitions.


In the mid-1990s, Harris had dated Brown, who was investigated by the FBI when he was speaker of the California Assembly and as mayor was dogged by conflict of interest, and she had benefited from his political patronage. As the speaker of the state Assembly, Brown had named Harris to well-paid posts on the California Medical Assistance Commission and Unemployment Insurance Appeals Board. As mayor of San Francisco in 2003, Brown was supportive of her district attorney campaign although they were no longer dating. Critics—including her opponents—were bemoaning cronyism at City Hall.

And so, when an audience member inside the church asked how, if elected district attorney, she could operate independently from Brown’s political machine, Harris was ready with not just an answer, but a counterpunch. “Make them understand that if they’re going to try to hurt you, they’re going to get more hurt,” Stearns said he counseled her.

“That was her cue,” Stearns said. Harris dismissed the question for its negativity while highlighting the most salacious elements of her opponents’ records, displaying a mix of flint and charisma that would one day lead her supporters to believe she could become president of the United States.

As Stearns tells it, Harris rose from her seat at the front of the sanctuary and stepped behind Terence Hallinan, the incumbent who billed himself as “America’s most progressive district attorney.” She told the audience, “You know Terence Hallinan has attacked Bill Fazio for being caught in a massage parlor,” a reference to a 1998 raid. Fazio, a former prosecutor who had run two close races against Hallinan and was now taking a third shot at the office, maintained he was there to conduct interviews for a legal case he was working on. He was never charged with any crime.

Then, Harris walked behind Fazio, Stearns said, and recounted the times her opponent had criticized Hallinan “for people having sex in his office,” referring to an incident in which two of Hallinan’s prosecutors were found in flagrante delicto inside the building.

“And then she walked back to the middle and said, ‘I want to make a commitment to you that my campaign is not going to be about negative attacks,’” said Stearns, who is still a Democratic strategist in the city. “’I believe we need to talk about the issues and the policies and the way we’re going to move our criminal justice system forward.”

The response was immediate. “People just jumped on their feet and gave her a standing ovation,” Stearns said. “And I was at the back of the church, and the look on the face of Terence Hallinan and Bill Fazio was, ‘Oh, shit.’’”

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Harris, now a U.S. senator from California who announced her candidacy for president on Martin Luther King Jr. Day, often speaks about her childhood growing up on the boundary between Oakland and Berkeley, the daughter of an Indian-born mother and a Jamaican-born father who pushed her in civil rights marches in a stroller. Her advisers believe that, like Barack Obama once did, Harris could appeal not only to white progressives in 2020 Democratic primary states like Iowa and California but also to black voters in the primary’s critical Southern states.

Harris has drawn on her record as a prosecutor, both in San Francisco and as California attorney general, to lend an intimacy to her progressive views on criminal justice reform. Yet she has struggled to reconcile her work as a prosecutor with the Democratic Party’s evolution on criminal justice in the age of the Black Lives Matter and #MeToo movements. Her first race for district attorney—and her entry into San Francisco’s fractious Democratic Party politics—reared her as a politician and offered a preview of her still-unfolding efforts to resolve those tensions with some of the party’s most leftward-tilting voters. San Francisco has sprung the careers of a catalog of Democratic politicians, including House Speaker Nancy Pelosi, Sen. Dianne Feinstein and California Gov. Gavin Newsom—all products, perhaps, of the intense, intraparty skirmishes in a politically homogeneous city of fewer than 1 million people.

“The San Francisco political arena is one of the most challenging, frankly, in America,” Art Agnos, a former San Francisco mayor, said. “We only have one member of Congress, two members of the Assembly, a state senator and a half representing the city.”

At the time of Harris’ race for district attorney, Brown ranked among California’s most powerful politicians. He had presided for 15 years over California’s state Assembly, and as San Francisco’s mayor, he had led the city through a period of rapid growth, muscling through the construction of a ballpark and housing and a renovation of City Hall. But Brown’s critics had long accused the mayor of wielding his influence to steer government contracts and jobs to allies, a charge Brown's supporters have denied. And as a relatively centrist, establishment figure, he was viewed warily by a generation of more progressive Democrats coming to power in the city.

At the time of Harris’ race for district attorney, Willie Brown (center) ranked among California’s most powerful politicians. | AP

Two years before Harris’ run, the San Francisco Chronicle ran a lengthy report on “Willie Brown Inc.” headlined, “How S.F.’s mayor built a city based on ‘juice’ politics.”

By 2003, the city’s entire political structure was in upheaval. The FBI was investigating allegations of corruption at City Hall. Hallinan was pursuing indictments against the city’s police chief and members of the department’s command staff, accusing them of being involved in a cover-up after three police officers were involved in a fracas over a bag of takeout fajitas. And a member of the San Francisco Board of Supervisors called police after a shouting match with Brown on the steps of City Hall. He had been worried, the Los Angeles Times reported at the time, that the mayor had “friends who are thugs” and he wanted to file a report “in case I go missing.”

Histrionics? Maybe. But a decade later, a sitting state senator from San Francisco, Leland Yee, was ensnared in a wide-ranging racketeering probe in which he admitted to taking bribes and agreeing to facilitate an illegal arms deal involving the importation of automatic weapons from the Philippines. The investigation, involving a crime ring run by a man named Raymond “Shrimp Boy” Chow, also felled Keith Jackson, a former school board member and prominent political consultant.

Eric Jaye, a political strategist in the city, said Harris’ emergence from San Francisco politics reminds him of Andy Dufresne, the Tim Robbins character from The Shawshank Redemption. “Andy Dufresne,” he said, quoting a line from the movie, “who crawled through a river of shit and came out clean on the other side.”



***

One of the first references to Harris in the San Francisco press came in 1994, when Herb Caen, the San Francisco Chronicle columnist, introduced the prosecutor to readers as Brown’s “new steady,” noting that at a celebration of Brown’s 60th birthday, Clint Eastwood had spilled champagne on her.

The following year, Caen chronicled the end of their relationship in similarly misogynistic terms—and with a comparison of Harris to other women Brown had dated: “This news came as a shock to many, including those who found Kamala Harris attractive, intelligent and charming. As a mutual friend once observed, ‘Willie has finally graduated from girls to a woman.’”

It is difficult to find any successful politician in San Francisco who does not have history with Brown. Before being elected mayor of San Francisco the same year Harris ran for district attorney, Newsom owed his start in San Francisco politics to an appointment by Brown to the city’s Parking and Traffic Commission, and later, to the San Francisco Board of Supervisors. Even so, Harris’ critics used the relationship to contend that she was not independently qualified to hold office and that, if elected, she would hesitate to investigate corruption at City Hall.

“At the time, anyone associated with Willie Brown was seen as part of the Brown-Burton machine,” Jeff Adachi, the city’s public defender, said, referring to John Burton, a former congressman and state Senate president. “Is there a machine? Yep. Was that machine in control of San Francisco politics for many years? Yeah, it was.”

Still, in Harris’ case, Adachi said “it wasn’t fair that somehow they were insinuating that somehow she was not qualified. The thing of it was, she had very strong qualifications coming into the D.A.’s office because she had worked her way up the ladder.”

Harris, in a 2003 interview with SF Weekly, pledged that “if there is corruption, it will be prosecuted,” and acknowledged that Brown constituted an “albatross hanging around my neck.” An early focus of her campaign was to shed it. Stearns, who described himself as “on the opposite side of the political spectrum from Willie Brown,” said he was selected as Harris’ consultant in part because Harris and her confidantes “wanted a person to run their campaign who was seen as independent from the power structure and would therefore give her an ability to communicate to a whole spectrum of activists and voters who might have been closed off to her.”

Rebecca Prozan, who managed the campaign’s day-to-day operations, said, “No woman likes to be judged by their relationships. We want to be judged by who we are, not who we are romantically involved with.” But Harris “knew as she was coming in … that there was no way that was not going to be raised as an issue,” she said.

Brown, who at the time was married but separated from his wife, declined to comment to POLITICO.

Yet it was not only Brown that Harris had to overcome to win her first political race. Then as now, it was also her 13-year career as a prosecutor—rife with hard judgment calls for her opponents to exploit. And Harris was running for office in the rare American city where, even in a race for district attorney, prosecutorial experience was not necessarily a boon.

The 2003 campaign for Harris, seen here in a official portrait taken a year later, was her earliest political effort to pre-empt such charges by defining her prosecutorial career as a left-leaning enterprise. | AP

She had started her career as a lawyer in 1990, after graduating from Howard University and the University of California's Hastings College of the Law, at the Alameda County district attorney’s office in Oakland. From there, she was recruited to the San Francisco district attorney's office to run the department’s career criminal unit. As the 2003 race for San Francisco district attorney began, she had recently left for the city attorney’s office, where she began mulling a campaign against Hallinan, her former boss.

“A lot of people told her not to run,” said Debbie Mesloh, a Democratic strategist and longtime friend of Harris. Hallinan was a former defense lawyer who came from a well-known family of progressives. Mesloh described the Hallinan family as iconic and said Harris still refers to San Francisco politics as a blood sport.

Harris’ professional record still draws criticism in progressive circles. Just this month, the New York Times published an opinion article by Lara Bazelon, a former director of the Loyola Law School Project for the Innocent, headlined, “Kamala Harris Was Not a ‘Progressive Prosecutor.' ”

Harris’s 2003 campaign was her earliest political effort to pre-empt such charges by defining her prosecutorial career as a left-leaning enterprise. In campaign mail to San Francisco voters that year, Harris promoted her opposition to the death penalty and her support for treatment programs for first-time, nonviolent offenders. She vowed to help keep children out of gangs and advocate for tenants mistreated by landlords.

Harris positioned herself, Mesloh said, as “someone who’s progressive, but someone who prioritizes accountability.” The message differentiated her from Hallinan, whose tenure had become marred not only by the “Fajitagate” scandal, but a backlog of cases and low conviction rates.

“It was incredibly frustrating, and not just in terms of the day-to-day work,” Harris wrote in her memoir, The Truths We Hold, published this month. “I believed the district attorney was undercutting the whole idea of what a progressive prosecutor could be. My vision of a progressive prosecutor was someone who used the power of the office with a sense of fairness, perspective, and experience, someone who was clear about the need to hold serious criminals accountable and who understood that the best way to create safe communities was to prevent crime in the first place. To do those things effectively, you also need to run a professional operation.”

Harris asked Fazio in late 2002 if he was going to run for a third time against Hallinan, he said. When Fazio replied that he was, she told him she had decided to run, too.

Fazio recalled her saying, “I think it’s my time.”



***

With a mayoral race and a historic gubernatorial recall election unfolding in 2003, the district attorney’s race in San Francisco was not a major draw. But Harris wanted the job. By late 2002, she was organizing her campaign, soliciting money and lining up endorsements.

Gary Delagnes, a former president of the city’s police union who would later have a falling-out with Harris over her refusal to seek the death penalty in the case of a young police officer who was shot to death while on patrol, recalled a party where Harris approached him to ask for his support. “I was standing in the corner,” he said. “I didn’t know who she was … and she came up to me and she put her finger in my chest and she said, ‘You better endorse me, you better endorse me. You get it?’

“I took it as almost half-kidding, but also very serious, that, ‘Hey, I’m going to win, and you better endorse me,'” he said, the implication: “I’m a player and I’m going to be a player and you better get on board or get out of the way.”

“I never forgot it,” Delagnes added. “She’s an intelligent person. She is a—let’s see, I better pick this world carefully: Ruthless.”

At the start of the race, Harris did not appear likely to advance to the runoff. In her own campaign’s initial polls, she stood at about 6 percentage points. “She was unknown by a vast majority of voters,” said Mark Leno, a friend of Harris who was then a state assemblyman organizing her campaign.

Harris’ early polling, however, revealed an opening. In one survey, her consultants found that about two-thirds of likely voters supported Hallinan’s progressive policies, but about half of those people did not feel he was putting them into effect.

“That pretty much determined our strategy,” Stearns said. “That was our centrist kind of position, which is: ‘We’re progressive, like Terence Hallinan, but we’re competent like Terence Hallinan is not.'”

To Harris’ right, Fazio drew support from more moderate parts of the city. In San Francisco, he told me, an endorsement he received from local Republicans one year “turned out not to be a blessing in disguise."

"It turned out to be just at terrible thing," he said. "It was like a group of child molesters had endorsed me.”

He had thought being a good prosecutor was enough to win the election, calling himself “totally naive” and adding, “Kamala, she had connections to the mayor, which gave her access to a lot of money people up in Pacific Heights.”

In addition to connections that Harris had through Brown, she developed her own network in San Francisco’s legal community and through her work with religious and charitable organizations that often intersect with the law. The Rev. Amos Brown, a civil rights activist in the city and former member of the Board of Supervisors, said he met Harris when she was a prosecutor in Oakland and he was helping a young defendant. In 2000, she worked on his unsuccessful reelection campaign, he said.

Despite warnings from her consultants that the location was too remote, Harris opened her campaign headquarters in San Francisco’s Bayview-Hunters Point neighborhood, a historically nonwhite area in the city’s southeastern corner. The campaign, she recalled last year, was “total retail.”

“Do you guys know about campaigning with ironing boards?” she asked a group of reporters in Iowa before the midterm elections, to which no one responded that they did. “When I first ran for office, for D.A., I would grab my ironing board, I’d put it in the back seat of my car. I would then go to the local grocery store with my posters and duct tape. … Then I’d get out of my car, I would open the ironing board in front of the grocery store, because, you see, ironing boards were the first standing desk.”

In her later campaigns—for state attorney general and U.S. Senate—Harris would come to rely, as all California politicians do, on television advertising. But in 2003, she said, “I’d walk up and down the hills and knock on doors, I’d stand at bus stops starting at 6 in the morning until 8 at night, begging people to talk to me on their way to work.”

Harris raised money aggressively. She raked in more than $100,000 before December 2002. By the end of the campaign, she had raised and spent money so prolifically that the city’s ethics commission found Harris violated a pledge not to exceed a voluntary $211,000 spending cap. The Harris campaign apologized and said it was a misunderstanding, according to the Chronicle. She used the money to bombard voters with mail touting her progressive credentials.

Yet by Labor Day of 2003, Harris was still polling between 6 percentage points and 8 points.

Prozan recalled a meeting with Harris around that time. “I looked at her,” she said, “and I was like, ‘You’re at 8 percent. What am I supposed to do with that?’ And she said: ‘You just need to get me into the runoff. If you can get me into the runoff, Rebecca, I can win this race.'”

The Chronicle provided her with a lift, and so did her opponents. Endorsing Harris in October 2003, the newspaper wrote that Harris “offers the best hope of repairing the damage inflicted on that critical city office during the past eight years of Hallinan’s reign.”

The morning the endorsement was published, Prozan said, Harris called her at 6:30 a.m. “There had better be enough Chronicle endorsement flyers for me to hand out to voters,” the consultant recalled Harris saying.

Harris’ campaign juxtaposed a color photograph of Harris with black-and-white photographs of Hallinan and Fazio in a mailer that listed the reasons the Chronicle had endorsed Harris.

The race tightened. Then, just days before the election, Fazio’s campaign resorted to a mailer that hit Harris for her relationship with Brown. The Chronicle at the time described the mailer as being sent to 35,000 voters with a photograph of a woman and the quote, “I don't care if Willie Brown is Kamala Harris’ ex-boyfriend. What bothers me is that Kamala accepted two appointments from Willie Brown to high-paying, part-time state boards—including one she had no training for—while being paid $100,000-year as a full-time county employee.”

“They were dumb to do it,” Stearns said.

Even after the Chronicle endorsement, Harris entered the weekend before the election 5 percentage points behind Fazio and 10 points behind Hallinan, according to an internal tracking poll by a mayoral candidate, Stearns said. The Fazio campaign’s attack backfired and afforded Harris an opportunity to move up. In a recorded telephone message to likely voters that weekend, she addressed the criticism while dismissing it, as she had at the forum months earlier.

The closing argument for Harris' campaign: Photos of over 100 years of San Francisco District Attorneys, all white men.

The ad had made Fazio “seem like a desperate, dirty campaigner who’s doing something I don’t agree with,” Stearns recalled. In contrast, “here’s this fresh, articulate woman calling me on the phone and walking me through it."

Harris vaulted past Fazio and into the runoff, where she defeated Hallinan in a landslide and became the state’s first African-American district attorney. Not only did she cut into Hallinan’s progressive base—especially with black and female voters—but she also carried more conservative areas of the city, garnering votes that had gone to Fazio.

The campaign’s closing argument was, Prozan said, “one of the most effective mail pieces that we did.” The words were familiar and prosaic: “It’s time for a change.” The images told the story. Harris’ staff had gone to the library and retrieved photographs of more than a century’s worth of San Francisco’s district attorneys, every one from 1900 to 2003. They were all white men.