Kamala Harris’s Early Career Involved Courtrooms and the Social Elite

In August 1996, a jury in an Oakland, Calif., courtroom convicted a man of slicing off a portion of his girlfriend’s scalp. The prosecutor was Kamala Harris, and the gruesome case was one of the few that made news early in her career.

“It was a vicious crime,” Ms. Harris told The Oakland Tribune. She was in her seventh year as a rank-and-file prosecutor in Alameda County, doing battle with suspected drug lords and murderers in Oakland, which was still contending with the crack epidemic.

Weeks later, Ms. Harris was back in the news, this time across the bay in San Francisco as a boldface name in the society pages, among the young and fashionable who had gathered for a martini party at a Polo Ralph Lauren store ahead of the Fall Antiques Show. It was hosted by a group of art lovers who called themselves the Young Collectors, raising money for underserved children while collecting “antiques, art, knowledge — and parties,” Pat Steger, The San Francisco Chronicle’s society editor and columnist, wrote.

During these formative years, when Ms. Harris was in her 20s and 30s, her life ran along two tracks that proved pivotal to her political ascendancy. By day, she developed the courtroom skills that have shaped her methodical approach as a candidate. By night, she moved through San Francisco high society, nurturing the financial and political connections that became instrumental in her national rise.

Ms. Harris, who grew up in a modest neighborhood in Berkeley, Calif., with a single mother, showed a talent for forging relationships with some of California’s most influential elites while she was still a young prosecutor.

She dated Willie Brown, one of the most powerful legislators in state history who became mayor of San Francisco. She cultivated relationships with Susie Tompkins Buell, the founder of two iconic clothing brands, and Laurene Powell Jobs, a businesswoman who was married to Steve Jobs, the entrepreneur who made Apple a tech powerhouse.

“The ability to have people want to open up to you is not that different in a courtroom than it is in a cocktail party,” said Teresa Drenick, who worked with Ms. Harris as a prosecutor in the 1990s.

The Gritty Streets of 1990s Oakland

The Alameda County District Attorney’s Office was for decades known as a place for ambitious lawyers to cut their teeth. When Ms. Harris arrived, Oakland was struggling at the tail end of the crack epidemic, and the war on drugs was in full force and homicides were at near record levels.

“When I was coming out of law school and you wanted to be a D.A., you wanted to be either in Alameda County or Manhattan,” Ms. Drenick said. “Those were the golden rings of D.A. offices at the time.”

A few years before Ms. Harris joined the office, Felix Mitchell, an infamous drug lord in Oakland whose career was an inspiration for the movie “New Jack City,” had been arrested by the F.B.I. and later stabbed to death in prison. That led to a leadership vacuum on the streets, as new drug bosses violently competed for territory.

“The Oakland that me and Kamala came into was an Oakland where his top lieutenants and new players in the game were recarving up Oakland,” said Terry Wiley, a former prosecutor who joined the Alameda office the same year as Ms. Harris.

Centrist Democrats, including President Bill Clinton and Joseph R. Biden Jr., who was a powerful senator of Delaware at the time, advanced tough-on-crime policies that flooded cities with police officers and that used incarceration to fight drug use. Black communities were devastated by the harsh sentences that were imposed on crack cocaine but that weren’t applied to the powdered version of the drug favored by wealthier white people.

Ms. Harris traveled down the path of a new prosecutor — first misdemeanors, then felony preliminary hearings, then felony trials.

She lived in Oakland, where the housing was still affordable, scooping up a one-bedroom condo near Lake Merritt for $116,000. She drove a Toyota Corolla and wore skirt suits in the time before pants were considered acceptable for women lawyers.

Her days, she recalled in her memoir, regularly included poring over autopsy photos with the coroner and trying to get survivors of rape to talk while they recovered at the county hospital.

A Splashy Debut in High Society

By early 1994, Ms. Harris entered San Francisco’s society circles with a splash in the column of Herb Caen, the dapper and influential columnist for The Chronicle who was close friends with Willie Brown, then the speaker of the California State Assembly.

Appearing in Mr. Caen’s column was the San Francisco version of a mention on Page Six of The New York Post, where Ms. Harris’s future challenger for the White House, Donald Trump, was showing up regularly.

Mr. Caen’s column that day in 1994 had an item about Mr. Brown’s star-studded surprise birthday party — Barbra Streisand and Clint Eastwood were in attendance — at a Beverly Hills mansion.

Mr. Eastwood, Mr. Caen reported, ended up spilling champagne on “the Speaker’s new steady, Kamala Harris, an Alameda Co. deputy D.A. who is something new in Willie’s love life. She’s a woman, not a girl. And she’s black.”

Mr. Brown was married, but he and his wife, Blanche Brown, had lived separate lives since the 1980s. The speaker liked to joke that his age plus the age of his girlfriend could not exceed 100. At the time, he was 60 and Ms. Harris was 29.

Ms. Harris was among several future political stars whose careers were propelled by Mr. Brown; that list included Gavin Newsom, now the California governor, and London Breed, the mayor of San Francisco. Mr. Brown appointed Ms. Harris to two state boards, and he gave her an expensive present: a BMW to drive to Sacramento for meetings.

Society columnists closely tracked Mr. Brown and Ms. Harris, commented on her fashion choices and referred to her as “stylish, slender, successful and very social.”

The couple attended San Francisco Symphony galas and celebrated the wedding of Mr. Caen’s son at Grace Cathedral and Mr. Brown’s 61st birthday at a party where Ray Charles performed. They shot pool at Tosca, a legendary North Beach bar, during an episode of ABC’s “Primetime Live,” which profiled Mr. Brown, by then the mayor of San Francisco, and his flashy lifestyle. The couple traveled to Paris together and attended the Academy Awards.

While Mr. Brown may have given her entree into those spaces, Ms. Harris’s charisma was a force of its own, several political contemporaries recalled.

Mark Leno, a former state senator from San Francisco, recalled meeting her at a mayoral campaign event for Mr. Brown in 1995 and being struck by her star power and easy banter.

“I thought, Who is this woman?” Mr. Leno said, adding that they became fast friends, dining regularly over Caesar salads at the city’s popular Zuni Café.

Ms. Harris became a trustee of the San Francisco Museum of Modern Art, where she started a program to connect students with art mentors. Danny Glover, the “Lethal Weapon” actor and a San Francisco native, was the chairman of the new effort.

After Mr. Brown was elected mayor of San Francisco, Mr. Caen described Ms. Harris as “the new first-lady-in-waiting.” Shortly after, though, Ms. Harris broke off the relationship when it became clear there was no real future with Mr. Brown, the former mayor has said.

Ms. Harris has excised Mr. Brown from her life story, never mentioning him in her two memoirs. She has bristled at the notion that he launched her career.

As she campaigned for district attorney eight years after breaking up with Mr. Brown, she told SF Weekly, “His career is over. I will be alive and kicking for the next 40 years. I do not owe him a thing.”

‘My Original Gangsters’

In 1998, Ms. Harris left Alameda and became an assistant district attorney in San Francisco overseeing the career criminal unit under Terence Hallinan, the progressive district attorney known as “Kayo” for his earlier life as a boxer.

While San Francisco was regarded in prosecutor circles as less prestigious than Alameda, Ms. Harris saw a better opportunity there to seek the top job. There were too many good lawyers in Oakland with their eyes on running for office, said Nancy O’Malley, the former Alameda district attorney who oversaw Ms. Harris’s work.

“When Kamala went over there she knew she was going to take him down,” Ms. O’Malley said, referring to Mr. Hallinan. “She was assessing, frankly, the landscape everywhere to see where she could go to move up.”

There, the two worlds she had been inhabiting — courtrooms and high society — came together, propelling her future political career.

In her first trial in San Francisco, a robbery case, Mr. Brown, who was still the mayor but no longer her boyfriend, dropped by the courtroom to watch Ms. Harris’s closing arguments. “The jury was a bit taken aback by the mayor’s presence in the otherwise empty spectator’s gallery,” one of the city’s gossip columns noted.

Ms. Harris left in 2000 to work for the San Francisco city attorney, but she didn’t stay away from the prosecutor’s office for long.

When Ms. Harris decided in 2002 to run for district attorney against Mr. Hallinan, the bonds she had cultivated with political elites in San Francisco paid off. Few were more important than her relationship with Ms. Tompkins Buell, the founder of the clothing brands Esprit and The North Face, whose daughter, Summer Tompkins Walker, had befriended Ms. Harris through the city’s social scene.

Ms. Tompkins Buell’s husband, the real estate developer and Democratic Party mega-donor Mark Buell, agreed over cheeseburgers to become finance chairman for her campaign. He took the meeting as a courtesy but was quickly won over, Mr. Buell said in an interview.

He assembled a finance committee that included Vanessa Getty, the daughter-in-law of the oil tycoon Gordon Getty, and Susan Swig, the daughter of Richard Swig, the chairman of Fairmont Hotels. They paved the way for the who’s who of San Francisco society to host receptions for Ms. Harris, each of which generated healthy sums of cash. (Ms. Harris spent thousands of dollars on flower bouquets to thank the hosts of the events, according to Jim Stearns, her campaign consultant in the D.A. race.)

Rising politicians often court the wealthy, but this group was particularly fruitful, given the kind of stratospheric wealth that the Bay Area would accumulate during the tech boom over the next two decades.

Ms. Harris entered the race polling at just 6 percent, but she wound up beating her former boss, Mr. Hallinan.

“No one thought you could upset a sitting D.A.,” Mr. Buell said.

“It was really the beginning signs that when she puts her mind to something … ” he added, his voice trailing off.

That promise came full circle this summer.

It was July 2, 19 days before President Biden would end his re-election campaign and endorse her as the Democratic nominee. Ms. Harris stood before a small group of deep-pocketed, longtime friends at a private fund-raiser for the Biden-Harris ticket in San Francisco.

Joyce Newstat, a top Democratic Party fund-raiser, and her wife, Susan Lowenberg, a real estate executive, hosted about three dozen people for lunch at their condominium atop Nob Hill, with sweeping views of the bay. Ms. Harris seemed relaxed and happy to have traded Washington, D.C., for her former home of San Francisco, at least for a few hours.

She called those in the room — including the Buells — “my OGs” and then laughed as she explained that it meant original gangsters.

“The people in this room have been on this journey with me from the beginning,” Ms. Harris told them. “I miss San Francisco. It all started here.”

Audio produced by Sarah Diamond.

Susan C. Beachy contributed research.