Terence Hallinan felt like boasting about his new hire. It was 1998, and District Attorney Hallinan was already a legend in San Francisco politics. The son of an Irish Catholic attorney, he had grown up in a mansion, but had largely dedicated his legal career to defending the city’s most marginalised. He’d been a civil-rights advocate, committed to the principles of nonviolent protest, who also nurtured a life-long habit of resolving personal disputes with fist fights. Along the way, he’d cavorted with Janis Joplin and defended Patty Hearst. In any other major American metropolis, Hallinan’s profile would have made it impossible to become the city’s top law-enforcement officer. In San Francisco, it made him.
Hallinan wanted to talk about the young attorney he had just poached from across the bay in Alameda County. “She’s a terrific prosecutor and has a great reputation,” he told reporters. “We’re all very excited.” He was talking about Kamala Harris, then an outsider who was about to take her first step on a steep ascent that has led through California politics, the US Senate and the vice-presidency. Now Harris, 59, stands on the cusp of winning the White House.
The quickness of her rise galls Harris’s critics, who attribute it to a combination of opportunism and luck, rather than political skill. She did not, they will point out, have to compete in an open primary to win the Democratic presidential nomination, instead inheriting it when a faltering Joe Biden was privately shown the door by his party’s elders. They will also note the results of her 2019 primary campaign, which collapsed in dysfunction and recrimination before even reaching the first milestone, the Iowa caucuses.
In American politics, “San Francisco liberal” has been a reliable insult for decades. Unsurprisingly, Harris’s opponent, Donald Trump, has sought to go further, branding her “Comrade Kamala”. It’s true, the city’s current state is no advertisement for progressive policies. Its streets are haunted by fentanyl addicts, folded over and inert, as if inspecting the pavement. On a recent, ill-advised stroll through Sixth Street in the Tenderloin district I came across one being injected in the face by a companion. It was just a normal weekday morning in downtown San Francisco.
But most Americans misunderstand the city’s one-party politics. Power in San Francisco has always been more complicated than it appears from afar. Entrenched immigrant communities hold sway in a city whose permissive soul made it a hotbed of counterculture and a magnet for hippies, homosexuals, Black Panthers and others. Old money, from shipping and banking, mixes uneasily with new, from pharma and technology. And beneath a cutting-edge economy, labour unions thrive at the controls of an old-school urban political machine.
Far from fostering harmony, the Democratic party’s hegemony tends to make combat more vicious. “It’s a seven mile-by-seven mile fishbowl,” said Brian Brokaw, a political consultant who has worked with Harris. “Everybody knows everybody. Everybody has history. There are blood feuds.” In other words, in a single-party city, all wars are civil wars. It takes talent to break through and tenacity to survive.
“Think about San Francisco as an entire city of the Upper West Side,” said Peter Ragone, a veteran political adviser, variously describing it as incestuous, internecine and brimming with political talent. “There’s just an intensity to the politics of San Francisco that does not exist anywhere else.”
Harris arrived in Hallinan’s office to find the city’s power elite populated by a cast of characters, some of whom are still the country’s most powerful and well-known Democrats and several of whom have played decisive roles in this year’s election drama. They would include US Speaker of the House Nancy Pelosi, who represents San Francisco in Congress; the telegenic, liberal darling Gavin Newsom, the city’s former mayor, now California’s governor; veteran US House representatives Barbara Boxer and Barbara Lee; not to mention Jerry Brown, Dianne Feinstein and Willie Brown, former governor, senator and mayor, respectively.
During Harris’s early career, they mingled at near-nightly political events, all with the capacity to do favours or harm. “It’s all part of the knife fight . . . of San Francisco politics,” said Debbie Mesloh, who worked for Feinstein before leading communications for Harris in the district attorney’s office. “There’s alliances and enemies and, what shade of blue are you?” Harris “really transcended San Francisco’s parochial ruling class,” she said. But “there was a sense of: ‘Who do you think you are?’”
It was in this hothouse that Harris, a young politician with evident star power, learnt her craft and thickened her skin. Those formative years may be as good a guide as any to understanding a politician who, less than a month before the vote, still remains an elusive figure to many Americans.
Kamala Harris grew up across the Bay Bridge in the Flats neighbourhood of Berkeley, where the houses tend to be smaller and more modest than those in the hills above. Her mother, Shyamala Gopalan, was the daughter of an Indian diplomat, who came to America for graduate school at the University of California and never left. At Berkeley, Shyamala met Donald Harris, a Jamaican student who would go on to become an economist at Stanford. After having children the couple drifted apart and eventually divorced. “The only thing they fought about was who got the books,” Harris wrote of the split in her 2019 memoir, The Truths We Hold.
Shyamala became the defining figure in her daughter’s life. Despite her heritage, she made a conscious decision to raise her biracial daughters as African American. “She knew that in the US everyone would only see them as one thing,” explained Mark Leno, the first openly gay man elected to the California Senate and a longtime friend of Harris’s. Compared with Barack Obama, who struggled in his youth to make sense of his biracial identity, “Kamala has always known who she is,” he said. “And that’s because of her mother.”
When it came to university, Kamala went east to Howard, the historically Black college in Washington, DC, and then, after graduating with degrees in economics and political science, returned to the Bay Area to attend law school at Hastings. What shocked many was that Harris, who talks about her baby-stroller view of Berkeley’s 1960s Civil Rights marches, opted to become a prosecutor as opposed to a public defender. Harris’s explanation was that she viewed America’s criminal justice system, tilted against the poor and the non-white, as inextricably linked with social justice. She wrote of wanting to be “on the inside, sitting at the table where the decisions were being made”.
The misery of the world in which Harris chose to spend her days is hard to overstate. San Francisco’s Hall of Justice is a grim, concrete-reinforced counterpoint to the neoclassical beauty of its golden-domed City Hall. On a recent morning, a judge and public defender were debating whether to allow home detention for a baby-faced Honduran immigrant, who spoke no English and had no fixed address. The next case was a man accused of being involved in a robbery, during which a boy was shot in the head with an AK-47 and killed. “Oh, God!” his mother wailed when bail was denied.
After graduating in 1989, Harris took a full-time position in Alameda County, which encompasses Oakland, the poorer, grittier city across the San Francisco Bay. Nancy O’Malley, who would go on to serve as Alameda district attorney from 2009 to 2023, saw Harris as distinct from the other young prosecutors in the office. “She never had that ‘I don’t know what to do here’” thing, she said. “She always had a maturity about her. That’s what drew me to her.” O’Malley eventually recruited Harris to work for her in a unit specialising in sexual abuse and domestic violence.
One of Harris’s early cases involved a woman who had been scalped by her boyfriend with a dull knife. Harris also dealt with children who had been sexually abused, usually by a family member or neighbour. She was skilled in court. But she also displayed a rarer talent: the ability to win victims’ trust and then guide them through delicate testimony, without which cases would crumble. “She had this innate empathy and compassion,” said O’Malley.
By day, Harris would toil in the courts. By night, she was gravitating to the glittery world of San Francisco. She might be at the symphony opening with Leno or the Getty mansion with Newsom and other swells. She was, by all accounts, bright and beautiful. But there was some other, ineffable quality that made her shine. “It was impossible not to survey the room and have your eyes fixed on her,” said Leno, recalling his first encounter with Harris in a crowded union hall in 1995. “She’s just a presence.”
Among others, Harris befriended several of the grand dames of San Francisco society, who were decades her senior, like Cissie Swig of the Fairmont Hotel fortune. She also began dating Willie Brown, 31 years her senior, and perhaps the city’s most dazzling political character.
Born in 1934 in a small east Texas town that was still segregated, Brown made his way to San Francisco after high school. He worked as a janitor to put himself through law school and then built a legal practice representing prostitutes, pimps and other so-called undesirables. Nattily dressed, wily and razor sharp, he held the Speakership in the California State Assembly for 15 years before becoming San Francisco’s mayor in 1996. The machine he helped build dominated the city’s politics for decades. Even today at the age of 90, Brown is still considered by some “Da Mayor”, as he was known in office.
Opponents have criticised Harris for her relationship with Brown. When pressed, her current campaign tends to downplay him as a boyfriend from 30 years ago. But, as with most things concerning Brown, it’s complicated and defies easy characterisation. “I think he opened doors for her. He introduced her to people,” said Mark Buell, a prominent developer and philanthropist who played a pivotal role as an early Harris fundraiser. “Having Willie’s name attached to something is pretty credible.”
In 1994, before he was mayor, Brown appointed Harris to two well-paying side hustles, a $70,000-per-year seat on the board of the California Medical Assistance Commission and a $97,000-per-year post on the California Unemployment Insurance Appeals Board. Harris has defended those jobs by saying she did the work. “I think he saw talent and elevated it,” said Jason McDaniel, a politics professor at San Francisco State University. “And she proved it was the case.”
But it was Hallinan who brought Harris to town, hiring her in 1998 to start a major crimes division. Three years earlier, his election had been something of a watershed. At a time when the nation — and California — were building prisons and politicians were outdoing one another to appear tough on crime, Hallinan promised a more compassionate path. “I don’t see this right-wing Republican approach, this ‘lock ’em up for longer and longer periods of time’, as the only solution to crime,” he told The New York Times upon entering office.
Hallinan was following the family tradition. His father, Vincent, was a labour lawyer who ran for US president from a prison cell in 1952 on the Progressive party ticket. Vincent taught his sons to box, and Terence was good enough that he vied for a spot on the 1960 US Olympic team, sparring against a young Cassius Clay.
Like everyone in San Francisco politics, he had a long history with Brown. Because of his record of rabble-rousing, Hallinan was refused admission by the California State Bar after graduating law school. Brown, by then an ally, testified to his good character, helping win a reversal after a two-year legal battle.
Among Hallinan’s first acts as San Francisco’s district attorney was a wild swing. He fired 14 veteran prosecutors by leaving pink slips on their desks while they were out to lunch. (He later got into a fight at a local steakhouse as a result.) Hallinan managed to diversify the district attorney’s staff and delivered on some progressive promises. But, by his second term, the office was a mess. Files went missing. There weren’t enough computers. Its conviction rate, hovering around 50 per cent, was the lowest in the state.
“I could already see he was slipping,” said Fred Gardner, Hallinan’s spokesman at the time. Gardner, who went to work in the San Francisco district attorney’s office in 2000, remembered Harris as thoughtful and diligent. She recommended books and took the time to explain the office’s inner workings to him. She also became his go-to when he needed someone to speak to the media about the office’s opposition to a state ballot initiative that would give prosecutors more leeway to try minors in adult court.
He had a less flattering memory of another rising prosecutor: Kimberly Guilfoyle. A San Francisco native, Guilfoyle was dating Newsom, the scion of an old San Francisco family with business connections to Getty Oil and familial links to the Pelosis. Newsom had volunteered for Brown’s mayoral campaign and was later appointed as the youngest member of the San Francisco Board of Supervisors. (Currently, Guilfoyle is engaged to Donald Trump Jr.) “Kimberly was in my office every morning wanting to make sure she got put in touch with the more important media people,” Gardner recalled.
Guilfoyle’s ticket to cable television stardom was the second chair on a savage dog mauling case that convulsed the city. In January 2001, two Presa Canario dogs got loose in an apartment building in Pacific Heights and killed a 33-year-old woman as she was returning home with groceries. It turned out the husband-and-wife attorneys keeping the dogs were looking after them for a member of the Aryan Brotherhood, who was serving life in prison. (In another only-in-San Francisco twist, it emerged that they had adopted him and may have been romantically involved with him.)
Around the time Guilfoyle’s star was rising, Harris’s appeared to falter. In August 2000, she and half a dozen other senior prosecutors quit the district attorney’s office in protest at its mismanagement. Harris decamped to the San Francisco city attorney, leading a division focused on children and families. Then, in 2002, she announced her campaign for San Francisco district attorney. She was taking a swing at Hallinan. “It was very audacious to take on a city incumbent, who had the support of Nancy Pelosi,” her friend Andrea Dew Steele said of Harris’s decision to challenge Hallinan. “She said, ‘OK, Andrea. I’m ready to run for office. What do I do?’”
In Harris’s telling, the underdog campaign was a homespun affair. With Shyamala at her side, she went all over the city, lugging an ironing board that she unfolded and used as a desk to hold her campaign literature. She chose Third Street in the predominantly Black Bayview-Hunters Point neighbourhood for her headquarters to demonstrate that she intended to represent all San Franciscans.
One of her campaign advisers, Jim Rivaldo, was a living link to the city’s historic gay rights struggle. He had helped his friend Harvey Milk become the first openly gay man to win public office in California, when he claimed a seat on San Francisco’s Board of Supervisors in 1977. Milk and mayor George Moscone were assassinated a year later. News of the deaths was announced to the world by Dianne Feinstein, then president of the city’s Board of Supervisors, who went on to become mayor, before being elected to the US Senate.
Harris’s first campaign was Rivaldo’s last. This June, during a speech in Los Angeles, Harris paid tribute to her late friend, who died in 2007. Rivaldo, she said, had taught her how reactionaries would attempt to label you as subversive and opposed to American values. “That’s the pathology of it all,” she said. “That’s how it works.”
To build a war chest, Harris asked Mark Buell, the developer, to chair her finance committee. His wife, Susie Tompkins Buell, co-founded the Esprit and North Face clothing brands and is a close friend of Hillary Clinton. It so happened that Buell had a grudge against Hallinan for blocking his nomination to a city board years earlier. Over lunch at Balboa Cafe, a restaurant owned by Newsom, Harris explained her plans to modernise the district attorney’s office, cracking down on serious crime while investing in rehabilitation. “The more we talked,” Buell recalled thinking, “I realised she’s smart. She’s on the ball. Maybe she’s got a chance?”
At the time, only 6 per cent of voters knew who Harris was, according to campaign polling. In addition to Hallinan, she was also facing Bill Fazio, a well-known defence attorney who had run in the previous cycle. Buell decided it was essential to raise a lot of money fast to prove the seriousness of Harris’s campaign. In September 2002, he set a goal of $100,000 by year-end. They raised $100,500. “She’d talk them out of their money, because she made sense,” Buell said, recalling hours spent together in his office, as she dialled potential donors from his list of contacts.
“It’s time for new solutions,” was Harris’s mantra. Then 37, she presented herself as a fresh alternative who could combine Fazio’s toughness with a trace of Hallinan’s San Francisco eclectic values. Newsom, meanwhile, was vying to become mayor. “There was a lot of excitement in the air with these two young candidates,” Dew Steele recalled.
The incumbent did not appear to take Harris too seriously. Hallinan kicked off his re-election campaign with the endorsement of Woody Harrelson, the Hollywood star and avid cannabis user. He may have been distracted by a bizarre controversy known as Fajitagate, in which off-duty police officers beat up two men outside a bar, demanding their takeout food. Hallinan alleged a cover-up and went after the police force’s top brass, but his case eventually unravelled.
Steadily, Harris made gains. She won the early backing of Amelia Ashley-Ward, publisher of the Sun-Reporter, the city’s oldest Black newspaper. The endorsement was a difficult call. Hallinan’s father and mother had been dear friends to the paper. So had he. They would go to lunch on Fridays and chew the fat, Ashley-Ward recalled. “Sadly, we never spoke after that,” she said of her decision to endorse Harris. “It became really brutal because the DA had always been a white male, and here comes Kamala, this brilliant, beautiful Black woman,” she said, describing her friend as “tough”. But, ultimately, “a sister’s a sister”; the friend who checks in, who calls when you lose a loved one, who has the gumption to tell you you’re dating the wrong person, as Harris once did with Ashley-Ward. “And she was right.”
In October 2003, with the first ballot just weeks away, the city’s biggest paper, the San Francisco Chronicle, also endorsed Harris, calling her “highly competent, dedicated to law enforcement and a force for innovation”.
Then, on the eve of the election, Fazio played the Willie Brown card. His campaign sent out flyers to 35,000 voters with an unflattering picture of 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 move was an acknowledgment that Harris had gone from an afterthought in the race to a threat.
But it didn’t work. Fazio was eliminated after the first ballot. Hallinan came in first and Harris second, helped by her majority support among Black voters. Before a second round, the two faced off in a debate in which Hallinan repeated the Brown attacks, suggesting the mayor was seeking to use his protégé to control the district attorney’s office. Harris held her own, sounding at times like a daughter scolding a dissolute father. “Terry blames everybody for his problems instead of taking responsibility,” she said at one point.
It is not clear how much use Brown would have been to Harris, in any case, according to Jim Ross, a Bay Area political consultant. A whiff of corruption had by then settled on Da Mayor, and his popularity was in decline. “Brown was kind of letting Newsom and Harris sink or swim on their own,” Ross said.
Harris won 56 per cent to 44 per cent. It was the end of one San Francisco political career, and an era, and the dawning of another. In a factoid that Harris partisans still cite, she received even more votes in that contest than Newsom did in his mayoral race. Shyamala would look on as her daughter was sworn in at the Hall of Justice, the same day Newsom was inaugurated at City Hall.
The two have been inextricably linked and compared ever since. They are generational talents who come from the same political scene, with overlapping donors and even advisers. One is expansive and a natural at political manoeuvring, the other lawyerly and studious. One was practically to the Getty mansion born, the other was not.
After Biden’s disastrous televised debate with Trump this June, it was Newsom many progressives dreamt of replacing him with, not Harris. Biden’s extraordinary ousting was greatly helped along by Pelosi, 84, a giant in the Democratic caucus, who urged the president to think again about his campaign. Harris stood by, playing the loyal vice-president. Several San Francisco political operatives told me party elders expected Newsom to emerge as Biden’s replacement. If so, Biden foiled the plan by endorsing Harris within minutes of his July announcement that he would relinquish the party’s nomination.
Among Harris’s first acts as district attorney was to paint the dingy offices and to buy a new photocopier. She eventually boosted the office’s conviction rate beyond 70 per cent. Some complained that this was achieved, in part, by accepting plea deals as opposed to taking cases to trial. Harris also changed the office’s mindset when it came to crimes against women. She was not interested in vilifying prostitutes. Rather, she viewed them as victims in need of protection, especially teenagers. It was the traffickers who were to be targeted.
One of the accomplishments Harris touts most was the establishment of a programme known as Back On Track. The idea, as articulated in her 2009 book, Smart On Crime, was to address the causes of delinquency and so reduce the cases piling up in her office. Back On Track allowed non-violent, first-time offenders to clear a felony conviction from their record, provided they pleaded guilty and completed a programme, including parenting classes, community service, job training and remedial education. Lateefah Simon, whom Harris recruited to lead Back On Track, is now running for US Congress, representing a district that includes Oakland.
After Harris discovered a statistical correlation between high school dropouts and homicide victims and suspects, truancy became another focus. “I believe fighting truancy might very well be the single most important thing we can do to impact the future of crime in this country,” she wrote in Smart On Crime. Some of the punitive measures she championed, including criminal prosecution of parents whose children missed school, did not endear Harris to Democrats on the left.
All that was nearly undone a few months into her term. On the Saturday night before Easter, 2004, Isaac Espinoza and another police officer were patrolling the neighbourhood where Harris had headquartered her campaign, when they approached a man they suspected of carrying a gun. The 20-year-old withdrew an AK-47 from under his coat and began firing. Espinoza, who was married with a young daughter, died at the hospital.
Police were distraught and then infuriated when Harris announced that she would not pursue the death penalty, in keeping with a campaign promise. It was not only her decision that angered law enforcement, but the apparent speed with which she reached it. “She made the decision after just three days. My son wasn’t even in the ground yet,” Carol Espinoza, the officer’s mother, told the Los Angeles Times.
Espinoza’s funeral was held at Saint Mary’s, the city’s principal Roman Catholic cathedral, before hundreds of officers. Thousands more, from across the state, lined the streets outside. Inside the vast cathedral, Newsom praised Espinoza as a hero “who died a hero’s death”. Feinstein, by then a US senator, talked about the young officer’s plans to move up the ranks. Then she surprised everybody by calling for the death penalty. The crowd roared. Harris, who was also in attendance, had been given no warning. “She just poured fire on it,” a former Harris aide recalled in disbelief.
The new district attorney’s relationship with the police was forever impaired. Some viewed it as a form of hazing by Feinstein and the city’s old guard. Their message: Harris might have won office, but she had not truly arrived. Behind the scenes, she has never been particularly close to Feinstein or Pelosi, who is thought to be grooming her daughter as a successor.
The Espinoza case has been wielded against Harris in every election since, including by Trump. There are those who believe that the episode changed Harris, deepening her lawyerly sense of caution. Her tendency to prepare in all matters like a prosecutor going to trial is often held up as one of her great virtues, except when, as one former aide put it, “She does occasionally get into her head and blows it.”
One of the chief criticisms of the current campaign is that Harris’s team is playing it too safe, only deploying her at highly scripted events and shielding her from mainstream media. If she prevails, caution will have been deemed shrewd; if she loses, foolish. Newsom, critics will inevitably say, would have done it differently.
But it is unlikely he would have done better than Harris when she stood toe-to-toe with Trump during September’s debate. Over 90 minutes, the seasoned prosecutor did what no other contender, be it Ted Cruz, Jeb Bush or Hillary Clinton, had been able to do. She made him look small. Once again, she was the sensible pragmatist waiting out the older, male candidate’s semi-coherent tirades.
As she has in previous races, Harris has been slowly chipping away at her opponent, heavily outraising and outspending him and rolling out a vice-presidential pick that surprised odds makers and energised the Democratic base. By late September, according to NBC news, Harris’s favourability had jumped 16 points, the biggest increase for any politician since President George W Bush after 9/11. Even so, the race is likely to be extremely close. As of October 8, an average of national polls showed Harris and Trump neck and neck.
History suggests Harris will not buckle. Much like her match-up with Hallinan, her 2010 contest for California attorney-general was also a nail-biter. Harris was pitted against Steve Cooley, a moderate Republican and popular Los Angeles district attorney. Once again, she was the underdog. Leno, her friend, remembered people urging him to prevail upon her not to even run. “They would say, ‘Mark, I know she’s your friend but she can’t win.’”
In a debate between Cooley and Harris after she made it through a crowded primary, Cooley touted his unanimous support among police unions. Harris responded with an icy contempt that called to mind a warning Ashley-Ward had relayed to me: she’s nice and smart, but you don’t want to ruffle her. “I will take a back seat to no one on my law enforcement credentials,” Harris began. “I am a career prosecutor. I have personally prosecuted everything from drug crimes to homicides. I have looked in the eyes of mothers of homicide victims, and I have looked in the eyes of rapists and child molesters. And I have sent them to prison for very long periods of time.”
That race was close. Cooley prematurely declared victory around 10pm on election night, whereas Harris went home to rest. The count dragged on for weeks. It was agonising, Brokaw, the political consultant, recalled. As new results would filter in, sometimes bad ones, he would call the boss to report them. “There were a few days when it looked like our deficit was widening,” he said, before it turned decisively Harris’s way. But “she never panicked.”
Joshua Chaffin is the FT’s New York correspondent
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