SAN FRANCISCO — The rebuttal sounded something like a threat. That seemed to be Kamala Harris’s point.
It was December 2003, a final debate in the final days before the runoff election in Ms. Harris’s race for San Francisco district attorney against her onetime boss, Terence Hallinan. And Mr. Hallinan, the crusading progressive incumbent, was going low: Ms. Harris could not be trusted to prosecute city corruption, he suggested, because of her relationship with Willie Brown — the outgoing mayor, peerless local kingmaker and Harris supporter whom she had dated years earlier. “He has an interest,” Mr. Hallinan speculated, “in having a friend in the district attorney’s office.”
Ms. Harris conjured a different hypothetical. She would take on crooked actors of all kinds, she said. In fact, she already had a prospective target in mind.
“I will set up a public integrity desk,” she vowed, building to the velocity of a TV lawyer in full riff, “dedicated to dealing with investigating and prosecuting cases involving corruption by any public official — be it Terence Hallinan or anyone else.”
Mr. Hallinan seemed to wobble. “That really takes the breath away,” he said. Eight days later, Ms. Harris took his job away.
Sixteen years on, as a California senator seeking the Democratic nomination for president, Ms. Harris is not, by her own admission, the candidate of structural upheaval, like Senators Bernie Sanders of Vermont or Elizabeth Warren of Massachusetts. She is not an old-guard centrist, like former Vice President Joseph R. Biden Jr. But in a party weighing how best to counter President Trump’s boundless capacity for brawling, Ms. Harris is the one who knows how to hit hardest, friends say, because that is how you win in San Francisco.
The 2003 race, the first of her career, is where she learned.
“San Francisco is the bluest of blue,” said Tony West, her brother-in-law and longtime informal adviser. “All political wars there are civil wars. And so it’s like a family fight. And those are often the worst.”
For Ms. Harris, who was 38 when she ran for district attorney, the campaign arrived at an inflection point — a period of restlessness, according to former colleagues, in the career of a hard-charging deputy accustomed to straddling disparate orbits. After a decade of unglamorous work for local prosecutors and a studied induction into San Francisco’s social elite, a Candidate Harris was by turns a society-page veteran and a prolific loiterer at supermarket parking lots, unfurling an ironing board from her back seat as a canvas for campaign literature. She began her evenings at fund-raisers in ritzy Pacific Heights and ended them at the modest apartment where she lived alone in the city’s SoMa neighborhood, stretching across her living room floor to compose longhand thank-you notes to donors.
“She was always the candidate who was like, ‘I got everything done on my list. Did you get everything done on your list?’” said Jim Stearns, a top consultant to Ms. Harris in 2003.
Often enough, those lists included the kinds of strategic choices that seemed endemic to success in San Francisco politics, particularly against someone like Mr. Hallinan, known locally as “Kayo” (as in “K.O.,” for knockout) since his boxing youth.
When her pledge to obey a voluntary campaign spending cap proved nettlesome, Ms. Harris did not hesitate to reverse herself, earning a hefty ethics fine.
Eager to extract information about her opponent’s operation, a senior Harris aide once posed as a Hallinan volunteer over email under an assumed name, before being found out and told to attend a nonexistent rally at 10 p.m. on a Sunday.
And subjected to gendered insinuations that Mr. Brown, three decades her senior, had facilitated Ms. Harris’s rise by introducing her to the city’s ruling class, the candidate was quick to flag her rival’s own sensational baggage, accusing Mr. Hallinan of fostering a debauched workplace where prosecutors had sex in the office.
It is no coincidence that some of Ms. Harris’s sharpest moments as a national voice have come in political combat. As a senator, she has won viral recognition for her lacerating questioning during hearings. In June, she flattened Mr. Biden in a debate exchange over his warm remembrances of segregationist senators. After some polling stumbles since then, she turned her attention to Mr. Trump from the Houston debate stage on Thursday, comparing the president to the “really small dude” behind the curtain in “The Wizard of Oz.”
Yet if her 2003 run proved that Ms. Harris could thrive in campaign conflict, it was also an early lesson in the challenges of negotiating the party’s base, particularly for a politician more inclined toward within-the-system reform than simmering revolution.
In many ways, no 2020 candidate has faced a hometown electorate more analogous to today’s Democratic primary conditions than Ms. Harris has. Then, as now, she was a self-described progressive, introducing herself as a potentially history-making pick in a multicultural city of vanguard liberalism, parochial neighborhood factions and often staggering income inequality.
But Ms. Harris also ran unambiguously to Mr. Hallinan’s right in a place that prided itself on showing offenders compassion. “She was the moderate,” said Nathan Ballard, a friend who worked with her as a deputy city attorney. “She was somebody who wanted to prosecute criminals.”
Getting that chance meant subjecting herself to an unpalatable fate: confronting the two men who had helped her, to a point, and were now threatening to stand in her way.
“I mean, I know how to fight,” Ms. Harris said in an interview. “But most people like to avoid a fight if you can.”
For a short while, the office was big enough for them both.
After several years across the bay in Alameda County, Ms. Harris joined Mr. Hallinan’s team in 1998 as an assistant district attorney overseeing the career criminal unit.
Friends say Ms. Harris initially admired his instinct for empathetic prosecution, which prized diversion over jail for many nonviolent lawbreakers. She spent off-hours helping his 1999 re-election and took a particular interest the next year in trying to defeat a state ballot measure, also opposed by Mr. Hallinan, that effectively shifted many young offenders into the adult justice system.
This, it seems, is where some of the tensions began. Fred Gardner, an office spokesman at the time, said that Mr. Hallinan became concerned as Ms. Harris assumed a public-facing role in the ballot debate, growing suspicious that Ms. Harris might run against him. (Mr. Hallinan’s son, Brendan, said his father, now 82, was not able to give an interview.)
In Ms. Harris’s telling, the office, which Mr. Hallinan had steered since 1996, was tumbling into disarray — epitomized one afternoon, she said, by a mass firing of lawyers who returned from lunch to find pink slips on their chairs. “The place was falling apart,” Ms. Harris said in the interview. “People were urging me to run.”
She left in 2000 for the city attorney’s office. Mr. Hallinan did not attend the send-off. Some other lawyers stayed away, too, Mr. Gardner said, fearing that they would “get reported back to the boss as disloyal.” He estimated that half the office attended anyway.
No longer under Mr. Hallinan’s purview, Ms. Harris began considering a campaign to replace him in earnest. She produced a low-tech bio page, pressing a photograph of herself against the sheet and making multiple copies. “I think we went to, like, Kinko’s,” Ms. Harris said. “Very high-level, professional operation.”
Mr. Stearns, her consultant, cautioned that Ms. Harris was occupying a dangerous political space: the center — wedged between Mr. Hallinan and a more conservative challenger named Bill Fazio.
“He kind of scratched his head and said, ‘O.K., this is going to be difficult because you’re running up the middle,’” Ms. Harris said. “I have this saying, which is: ‘No good public policy ends with an exclamation point.’”
Ms. Harris, who has strained at times as a presidential candidate to convince progressives of her convictions, was asked if this tension felt familiar lately. “There probably are some parallels,” she said. “There’s an appetite for statements that end with an exclamation point. And it’s really challenging.”
Mr. Hallinan’s supporters believe his punctuation, as it were, was commendable for a district attorney, praising his commitment to rehabilitating drug users in the throes of the tough-on-crime era. Kenneth Wine, a longtime law partner of Mr. Hallinan’s brother’s, said that while Ms. Harris was “a good, honest, straightforward prosecutor,” she won the job in part by questioning the kind of progressivism that Mr. Hallinan championed.
“He shocked a lot of people with his progressive ideas,” Mr. Wine said. “Kamala Harris became the D.A. sort of backtracking on those to some extent.”
Ms. Harris liked to say there was nothing progressive about being “soft on crime.” Volunteers furnished doorknobs with fliers stuffed with muscular adjectives (“Tough. Fair. Effective.”), trumpeting her support from law enforcement groups. The headshots of local elected endorsers specked her campaign materials.
And about five or so faces into that roster — not so prominent as to draw immediate attention, not so buried as to suggest deliberate camouflage — voters were greeted by a smiling mayor.
The thing was, it could feel as though everyone who hit it big here owed a debt to Willie Brown — the showman power broker enamored of Brioni suits, well-directed patronage and his own legend.
The current California governor, Gavin Newsom, was a young businessman when Mr. Brown elevated him to the city’s Parking and Traffic Commission and, soon after, to the Board of Supervisors — placing Mr. Newsom on the fast track to succeed him at City Hall. The current mayor, London Breed, was once an intern in Mr. Brown’s administration.
Ms. Harris’s example is more complicated. She began dating Mr. Brown, now 85, around 1994, when she was working in Alameda County and he was speaker of the California Assembly. He appointed her to two well-compensated state posts. He gave her a BMW. He introduced her to people worth knowing.
“When I first met her, she was Willie’s girlfriend,” said John Burton, a former congressman and chairman of the California Democratic Party. “Everybody gets their start through somebody else. Jack Kennedy got his start through his father. Bobby got his start through Jack.”
Ms. Harris’s allies have bristled at any suggestion that Mr. Brown powered her ascent, dismissing the charge as sexist and making clear that she was plenty capable of impressing on her own. Few could argue that Ms. Harris, hovering around 5 percent in early polling, entered the 2003 race at much of an advantage, even as her fund-raising drew on an ungainly Filofax full of high-end contacts. (Eventually, friends insisted she transfer to a Palm Pilot.)
Fair or not, Ms. Harris understood quickly that Mr. Brown would shadow the campaign. “No woman likes to be judged by who she dates,” said Rebecca Prozan, a top 2003 campaign aide. “Was it something that we wanted to address? No. Was it something we had to address? Yes.”
Ms. Harris hoped to maintain distance without alienating his supporters. An internal memo suggested hiring Mr. Stearns as a consultant in part because he was associated with “the anti-Willie Brown camp which may be helpful.” Ms. Harris told SF Weekly in 2003 that she was so independent of Mr. Brown that he “would probably right now express some fright about the fact that he cannot control me.”
“His career is over,” she said, as Mr. Brown’s second mayoral term wound down. “I will be alive and kicking for the next 40 years.”
But Ms. Harris also promoted Mr. Brown’s support on her fliers. And his barely hidden hand helped propel her precedent-busting fund-raising. “He was instrumental behind the scenes,” said Mark Buell, a major Democratic donor who served as Ms. Harris’s finance chairman. “Willie Brown told me — and I didn’t want to believe him — you have to raise $1 million to win this race. And we did.”
Mr. Brown, who now writes political columns, cheekily declined to be interviewed, on the grounds that he could not assist a rival publication. “I write for The Chronicle,” he said, quickly ending a phone call. (In one of those columns in January, he wrote: “Yes, we dated. It was more than 20 years ago. Yes, I may have influenced her career.”)
Ms. Harris, in the interview, called her 2003 opponents’ references to Mr. Brown “frustrating” and “designed to degrade, frankly, the conversation about why we needed a new D.A.”
Asked if Mr. Brown was a factor in the race — either as a boogeyman deployed by her rivals or as a sitting mayor with an interest in the outcome — Ms. Harris said: “Um, I’d — you know. You can ask the pundits. I — yeah.”
Asked if she found the attacks misogynistic, she said, “I think most people think that that’s the case.”
Enough voters seemed to.
Just before the election, the campaign of Mr. Hallinan’s other challenger, Mr. Fazio, circulated a mailer quoting a woman critical of Ms. Harris: “I don’t care if Willie Brown is Kamala Harris’ ex-boyfriend,” it read. “What bothers me is that Kamala accepted two appointments from Willie Brown to high-paying, part-time state boards.”
The approach backfired. Former Harris aides credit public disgust over the mailer with helping to push her into the two-person runoff at the expense of Mr. Fazio, who had been polling ahead of Ms. Harris throughout the race. (Reached by phone, Mr. Fazio said he did not remember the mailer but suggested it sounded like “some desperation on my campaign’s part.” He said he supported Ms. Harris’s presidential run.)
Perhaps more relevant, Ms. Harris proved to be a relentless and versatile campaigner, parking herself at transit stops, gay bars and senior-center bingo sessions where she worried her hot streak one night might upset the regulars. She established her headquarters in the predominantly nonwhite Bayview-Hunters Point neighborhood, posing for photographs beneath an indoor graffiti mural that read “Justice” and watching her mother, Shyamala Gopalan Harris, instruct supporters on proper envelope-stuffing form.
Ms. Harris also excelled in more exclusive company. She held events with the musician Boz Scaggs and Eve Ensler, author of “The Vagina Monologues.” She persuaded the party’s powerful central committee to withhold an endorsement before the first round of voting, a major setback for Mr. Hallinan.
On the night of the runoff, Ms. Harris entered her victory party to chants of “D.A.! D.A.!” as “We Are the Champions” blared, relatives gathered beside the “Justice” mural and Mr. Brown held court with reporters.
Mr. Hallinan was terse in conceding defeat. “It’s a tough job,” he said, wishing Ms. Harris luck.
More recently, Ms. Harris has likewise found that the city’s politics can be fickle. Many of San Francisco’s progressive activists prefer Ms. Warren or Mr. Sanders. Mr. Buell, her 2003 finance chairman, remains a supporter but has also raised money for Mayor Pete Buttigieg of South Bend, Ind. “I think she’s a little miffed,” Mr. Buell said.
And in the city’s latest district attorney’s race, to be decided in November, Mr. Stearns has taken on a new client: Chesa Boudin, a public defender running on reducing mass incarceration.
“He is actively criticizing Kamala’s record,” Mr. Stearns said. “2003 has never seemed so much like yesterday.”
Kitty Bennett contributed research.