Three months after becoming San Francisco's district attorney in 2004, Kamala Harris faced a trial by fire.

Harris had just won her first run for office by positioning herself slightly to the right of her liberal predecessor and by promising to run a more professional office as the city's top prosecutor. She pledged to tackle domestic violence and sex trafficking and stand up for those who had felt ignored.

And she had promised never to charge the death penalty — a promise that was put to the test when a 29-year-old police officer, Isaac Espinoza, was shot and killed by a gang member.

Nevertheless, Harris kept her promise, announcing before Espinoza's funeral that her office would seek life without the possibility of parole.

At the time, Harris said she believed that the majority of San Franciscans wanted to see "the most severe crimes be met with the most severe consequences" and that in this liberal city, life without parole would likely be the most severe consequence a jury would hand down.

But former police officers' union president Gary Delagnes says the timing of Harris' announcement alienated many in the San Francisco Police Department.

"By having a press conference before the kid was even in the ground to announce that she was not seeking the death penalty, I mean, it was such a cold political move that, I mean, it just showed a complete lack of compassion," he said.

But while the timing of her announcement poisoned the young prosecutor's relationship with the police union, even Delagnes acknowledged that she made the right call in a progressive city where opposition to the death penalty is strong.

"Obviously, no San Francisco jury was going to convict a 19-year-old African American man — they're not going to give the death penalty to somebody in that situation, and I said that from the beginning," he said.

Harris' office did get the conviction and sent Espinoza's killer to prison for life, without the chance for parole.

Breaking boundaries

Throughout her time in politics, Harris has found herself caught between two very different groups that see themselves in her: law enforcement and progressive activists pushing for a more racially just legal system.

Harris is now the Democratic nominee for vice president and in recent years has been outspoken about the need for systemic change to policing and criminal justice in America.

But long before she was the second Black and first South Asian woman to serve in the U.S. Senate, when she became district attorney of San Francisco and then attorney general of California, she was considered an outsider by many in the world of law enforcement, says Debbie Mesloh, a longtime adviser to Harris.

"I recall many situations where people who had been in leadership within the DA's office or within the police department seemed to struggle with her leadership," Mesloh recalled. "That first meeting with the District Attorneys Association of California, she was the only woman to walk in that room. She was one of, I think, three people of color."

Mesloh said that throughout her career, Harris has had to absorb "subtle and not-so-subtle messages that were sent to her of, you know, 'Who do you think you are? You need to know your place. You know, you may have won an election, but there's only one of you. We outnumber you.' "

Mesloh said Harris never let those messages intimidateher.

Wanting a seat at the table

Suzy Loftus, who worked under Harris as both a deputy district attorney and assistant attorney general, said the conviction of the policeman's killer was important to Harris — and consistent with her principles. And, she said, Harris learned from the case.

"She made the decision quickly, announced it quickly and recognized later that there were so many people who were so deeply impacted in that moment and in grief and in pain. And that loss was exacerbated by an announcement in the middle of it. So I think she endeavored to learn from her mistakes," said Loftus.

That lesson? Don't rush out to make an announcement — take into account the public's pain and grief. But, Loftus said, it didn't make Harris a different or more cautious politician.

"I think by function of being a prosecutor, you're more careful," Loftus said.

Jim Stearns, who ran Harris' first campaign, said that while the Espinoza decision soured some in law enforcement on Harris at the time, it also won over many voters, making her something of a political star in San Francisco.

"I think what galvanized the city for her was this was the first time people could remember that a politician made a difficult promise, like, 'I will never enforce the death penalty,' and actually did it under the most incredible pressure," he said.

Stearns said there has been a tension throughout Harris' career: between what's expected of her as a member of law enforcement and what's asked of her by progressive activists who see themselves in her.

"Kamala has always wanted to have a seat at the table," he said. "So it would be a mistake to see Kamala or to expect from Kamala that she is ever going to stand outside of the system and demand the kind of wholesale changes that people who stand out of the system want."

That tension would play out most dramatically when Harris took on her next job, as attorney general of the state of California.

"Someone ... who's been so vilified"

In 2010, Harris won the narrowest of victories to become California's first female and first Black attorney general.

It was a tough race. Law enforcement unions had overwhelmingly backed Harris' opponent, Los Angeles' Republican district attorney, Steve Cooley, who used those endorsements to paint Harris as anti-police.

To build relationships with local prosecutors, sheriffs and police officers, the first thing Harris did when she became attorney general was to visit all 58 California counties. Loftus, her longtime deputy, planned the tour.

"It was incredibly effective, because I think there's nothing like actually getting to talk to someone — especially who's been so vilified," she said.

Four years later, when Harris ran for reelection, police groups largely supported her. But she soon found herself at odds with another key constituency: progressive Democrats.

Deadly police shootings were in the news, and Democrats in the California State Legislature were pushing a bill to require independent investigations of deadly use of force.

Sacramento Assemblyman Kevin McCarty authored a 2015 bill to require the attorney general to take away investigations of police shootings from local district attorneys, who, he said, have an inherent conflict of interest.

"You know, if you're at a high school baseball game looking out there and seeing the umpire is the uncle of one of the star players, are you going to trust that umpire to call balls and strikes fairly? The answer is no," said McCarty.

Harris opposed the bill, and it died. She also declined to support another bill requiring police officers to wear body cameras, even though she was the first to mandate them at a state agency, the California Department of Justice.

Still, her opposition to statewide legislation didn't sit well with the California Legislative Black Caucus. They saw her as on the wrong side of the fight.

Sen. Holly Mitchell, a Los Angeles Democrat and member of the Legislative Black Caucus, told the Los Angeles Times in 2016 that Harris' "absence is noticeable," adding that "people are looking to her for guidance and direction."

Now a lawmaker, not a law enforcer

It's not surprising for an attorney general to face such pressure — and that's especially true for one who is a Black female, said LaDoris Cordell, who was an independent police auditor in San Jose.

"There's this fine line. You're the top cop, but you're also a prosecutor which is representing the people. And oftentimes those two things are not compatible," she said.

Investigations of police shootings are in some ways a no-win situation, Cordell contends.

"The feeling is that people are passing around this hot potato. When these shootings happen, they're very controversial. The public is very aware. There are protests, and it's sort of like, you know, people just don't really want to handle them," she said.

Harris said her opposition to the bill wasn't based on fear of catching a hot potato, but rather concern about interfering with local prosecutors.

She knew firsthand how that felt: In 2004, some San Francisco officials pushed the then-state attorney general to take the Espinoza murder case away from her office after she declined to seek the death penalty.

Loftus, Harris' longtime deputy, says that experience cut deeply.

"I think she fundamentally always believed it's a local prosecutor's job to do the right thing and not to punt," she said.

Now that she's in the Senate and on the presidential campaign trail, Harris has been outspoken on policing issues, introducing legislation to ban chokeholds, racial profiling and no-knock warrants, as well as to make lynching a federal crime. In her speech accepting the Democratic nomination, she called out systemic racism in America, naming two recent victims of police violence, George Floyd and Breonna Taylor.

Mesloh, Harris' longtime adviser, said she's not taking those positions now because she has changed her mind: The difference is that she's now a lawmaker, not a law enforcer.

"Having worked with her for so long, these were conversations we would always have," Mesloh said. "She may have not been having them externally, but this is the Kamala that I have known and seen for 20 years."

Mesloh said that because of who Harris is — a Black, South Asian woman and the daughter of civil rights activists — she was often expected to align herself with liberals pushing for change from the outside. But for most of her career, she has been a prosecutor, working to change the system from the inside.

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