OAKLAND, Calif. — Two decades ago, LeRonne Armstrong and Danielle Outlaw bonded as trainees in the police academy here. Both had grown up in the city — he in West Oakland, she in East Oakland — and both were new parents in their 20s, each trying to balance the job with a young child at home.

Perhaps more important, both recognized that they were young, black, and from the community they would serve. And in Oakland, the birthplace of the Black Panthers in the 1960s and a city profoundly impacted by the War on Drugs 20 years later, young black residents had not traditionally rushed to join the force.

“We both came in understanding that this was bigger than just us,” said Armstrong, now an Oakland deputy police chief. “We took on the challenge of trying to be part of the change.”

Twenty years later, Outlaw’s career is about to hold broader significance once again — this time on a much bigger stage.

When she takes over Monday as Philadelphia’s police commissioner, she’ll be the first black woman to lead the department, which has been rocked by recent scandals over racism and sexual harassment in a city combating levels of gun violence not seen in years.

Interviews with nearly a dozen close associates and friends here — where she spent the first two decades of her career — reveal that in the insular and testosterone-filled culture of policing, Outlaw, 43, has long approached her work with ambition, confidence, and determination. Along the way, she developed unique allies both within and outside law enforcement.

She also has proudly infused her identity as a black mother of two sons — now 18 and 21 — into her management style, and she is unapologetically herself: short of stature and with several tattoos, a changing mix of hairstyles, a plainspoken and sometimes blunt communicator.

Friends say Outlaw, who just spent two years as chief in Portland, Ore., is committed to injecting her profession — often militaristic and wary of change — with fresh ideas. Some acknowledge that those aspirations have led to jealousy or skepticism from some colleagues.

If Outlaw had been seeking a larger platform, she has one now. Leading the 6,500-member Philadelphia Police Department is often considered one of the most challenging municipal police jobs in the country. And Mayor Jim Kenney made it clear in announcing her appointment — which comes with a $285,000 salary — that he expects her to confront race and gender discrimination claims, beleaguered morale, a long-standing lack of community trust, and a rising homicide rate.

Outlaw, through Philadelphia officials, declined to comment ahead of being sworn in. At her introductory news conference Dec. 30, she said she was “very qualified” to take over in Philadelphia, a bigger and poorer city than either Oakland or Portland, with nearly seven times as many police officers as either city, and more annual crime.

Armstrong, like others in Oakland, believes his former academy colleague is ready for the challenge.

“I think you guys will be surprised by what she can handle,” he said, describing Outlaw as “somebody who’s willing to be uniquely different than what you’ve had before.”

In East Oakland, Outlaw spent part of her childhood on a tidy block near 75th Avenue that offers sweeping views of the Bay Area. Her neighborhood sat between two sides of the city: the affluent and largely white communities perched in the hills above, and the poorer areas largely populated by minorities below.

Her father was a state transportation worker and her mother an AT&T employee, but she has not shared much about her personal life. As a teen, she spent much of her time in a leafy enclave of Rockridge, about seven miles from East Oakland, at Holy Names High School for girls — an institution that she has said “probably saved my life.”

Founded in 1868, the private Catholic school — one of Oakland’s first high schools — serves a racially and economically diverse population of girls, most of whom receive financial aid. The school has long been known for its arts programming and college training: In recent years, staffers say, every student has graduated and attended college, and alums have included prosecutors, musicians, writers, and local politicians.

Linda Brownell, who was an adviser to Outlaw’s class of about 60 girls in the early 1990s, said Outlaw arrived as an outspoken and opinionated freshman, and frequently pushed her classmates to question norms at the tradition-rich institution. Brownell said Outlaw — who twice served on class council — sometimes came across as brash, but ultimately learned to channel her inquisitiveness so effectively that she inspired even Brownell to ask administrators to try new things.

One example: Brownell said Outlaw’s class was the first to push to have a sleepover at school, in which students watched movies, played games, and bunked in the gym. The proposal required administrative approval and teachers willing to chaperone, but it was so successful, it remains a tradition.

“She helped me see that I could” branch out, said Brownell, now the school’s director of academic services.

During a two-week winter intersession at Holy Names, Outlaw participated in a ride-along program with Oakland police.

At the time, she didn’t think particularly highly of law enforcement. Her cousin had been arrested by Oakland police, Outlaw said in a 2018 TEDx Talk, adding that “as kids, we were told to run” from the cops.

But Outlaw was paired for a week with Officer Tim Sanchez. And watching him perform simple acts — getting food, joking with her, talking about the city — changed her perceptions of what law enforcement could be.

“I got to see Tim the human being,” Outlaw said in the TEDx Talk. “We had so much in common.”

Sanchez, in an interview, said he’d taken students on ride-alongs before and after Outlaw’s and always enjoyed them. Still, he was surprised by the impact this one apparently had.

“I didn’t know she thought it was that big of a deal,” said Sanchez, who retired in 2008. “You have a high school student in the car, they have no idea what they’re going do with their life. I don’t know that she talked about, or I talked about, her being a cop. What did stick out ... is just our connection with Oakland.”

He added: “I guess I sort of humanized the [job] for her.”

After graduating from Holy Names in 1994, Outlaw studied sociology across the bay at the University of San Francisco, a Jesuit school. As a junior, she had 15 minutes of fame appearing on Wheel of Fortune and winning $40,000. Onstage, when host Pat Sajak asked what she wanted to do after graduating, she said to go into law enforcement.

Her father was not thrilled by that career path, insisting it was a waste of a degree. But Outlaw pursued it anyway after college.

By the time she reached the police academy, she was a single mother with a 1-year-old son. Armstrong said he and Outlaw initially bonded because he also had a young child, making them the rare cadets who had to think about day care too.

Once out of the academy, Outlaw started her career in patrol. Sanchez, her former ride-along mentor, did, too. He said he sometimes worked with Outlaw, and the traits that drew them together when she was a high schooler served her well during her early days on the job.

“Growing up in Oakland meant it was tough for anyone to pull anything over on her, because she could see right through the bull—,” Sanchez said, calling her sharp, quick-witted, and street savvy.

“It was tough for anyone to pull anything over on her, because she could see right through the bull—.”

Outlaw spent only a short time as a patrol officer before she quickly began climbing the ranks, working in community relations, media relations, internal affairs, and as a patrol supervisor, among other roles.

Desley Brooks, a former city council member who chaired the public safety committee, said Outlaw seemed to be the rare Oakland cop who was genuinely invested in the city, in a department that traditionally attracted recruits from elsewhere.

“In law enforcement, I think there’s too much that’s done for show,” Brooks said. “She was engaged,” often staying at community events, such as block parties in Brooks’ East Oakland district, well beyond when other public officials or cops had left.

Barry Donelan, the head of Oakland’s police union, who took the test to become a sergeant at the same time as Outlaw, said she was hardworking, decent, and invested in keeping her colleagues safe.

In 2014, he said, Outlaw was tasked with a mundane and unpopular assignment: refitting every officer and squad car with a new police radio. Two years earlier, the radio system had famously failed while President Barack Obama was in town, and Donelan said the replacement effort was resisted by stubborn city workers on one side, and police union officials on the other who were desperate to have the radios installed quickly.

Donelan said Outlaw expertly managed the process, informing key stakeholders in personal meetings, and keeping in mind that successful installation could help protect police.

“She was good, because she had the same level of empathy and concern that I did,” Donelan said. “She got it. She pushed it over the goal line.”

Oakland had plenty of turmoil while Outlaw was on the force, leading her to seek some unconventional allies.

One was Janeith Glenn-Davis, about a decade older than Outlaw, and the highest ranking woman in the department in 2000. She was expected to be promoted to captain that year, but was passed over after becoming pregnant. The job remained vacant until Glenn-Davis went on maternity leave. Commanders then promoted someone else.

Glenn-Davis sued for discrimination in 2002 and left Oakland to become police chief at California State University, Hayward. A federal jury ruled in her favor and awarded her $2 million.

Despite her tumultuous departure, Glenn-Davis said that Outlaw sought her out for advice about being a woman and a leader while navigating the ranks. The two would chat several times a month, said Glenn-Davis, who described Outlaw as “really good at seeing things in people” and unafraid to seek advice from any corner.

Outlaw also developed a working relationship with John Burris, a civil rights lawyer who had made a career out of suing the Oakland Police Department. One of Burris’ biggest cases began in 2000, when he sued over a scandal in which four Oakland cops were accused of assaulting and planting drugs on suspects.

The suit resulted in a $10.9 million settlement in 2003 in which the police department agreed to work toward reforms. Burris said Outlaw seemed to view the scandal as an opportunity to improve the department, particularly in reforming practices for recruiting, screening, and hiring candidates. But because she did not have final say, he said, her ideas could only go so far.

“She didn’t always feel good about what was going on there,” Burris said, adding that Outlaw sometimes shared frustrations with him if she felt she had been “overruled by [a] good ol’ boys network."

An example came to light in 2016, when Oakland again attracted international attention for a police scandal. Several officers were accused of having sex with a teenager and trying to cover up the alleged encounters. In the aftermath, the department cycled through three chiefs in just nine days, with the mayor saying: “I am here to run a police department, not a frat house.”

Outlaw by then had been promoted to deputy chief, and said publicly that the department would bolster its background checks and make training classes smaller to try to ward off problematic recruits.

But Outlaw already had been advocating behind the scenes for such reforms for years, Burris said.

“I think she recognized she could scream about things all she wanted,” he said. “But she couldn’t change it.”

Glenn-Davis wouldn’t say if Outlaw complained about the department during their discussions. But she had no doubt that Outlaw had been underestimated because people viewed her as “a woman with kids.”

To achieve the rank she did in Oakland, Glenn-Davis said, Outlaw “already had to be better than a lot of people.”

Glenn-Davis, now retired, said Outlaw also had become friendly with Glenn-Davis’ husband, Ron Davis, a former Oakland cop and East Palo Alto police chief who later headed the federal Office of Community Oriented Policing Services.

Davis is a Philadelphia native who now runs a consulting company that counts former Commissioner Charles H. Ramsey as a partner.

Ramsey said in an interview that he met Outlaw a few years ago when he was president of the Major City Chiefs Association, and that he had a mostly congratulatory discussion with her after her appointment in Philadelphia was announced.

Burris said he believed Outlaw’s widespread and diverse networking led to some jealousy within Oakland’s department, and caused skepticism among peers that may have kept her out of the “in crowd.”

Tony Ribera, a former San Francisco police chief who helped recruit Outlaw to serve on an advisory board for a criminal justice institute at the University of San Francisco, said her time in Oakland likely taught her the importance of having a trusted inner circle while remaining decisive and clear about her objectives.

“She’s not going to equivocate,” he said.

Glenn-Davis said of Outlaw: “There’s no shame in her game … Folks are going to underestimate her. And that’s going to be a mistake.”

In 2017, following the teenage sex scandal in Oakland’s police department, the mayor tapped an outsider, veteran law enforcement official Anne Kirkpatrick, to be the city’s new chief.

Later that year, Outlaw left her hometown, accepting the job as chief in Portland.

Her time there included controversies over how police handled protests, and about tactics regarding when officers used force against mentally ill people. She also acknowledged publicly that being an outsider, and the first black woman to lead the department, came with challenges, including being viewed as a “diversity hire.”

When she announced last month that she’d accepted an offer to lead Philadelphia’s force, some in Portland grumbled that it seemed as if Outlaw had used the city as a stepping-stone — and others said she hadn’t reformed the culture after only two years.

Her appointment in Philadelphia comes with similar expectations of culture change. How Outlaw structures her command staff to achieve that remains to be seen; 18 internal candidates were interviewed for the job, and two of the three current active deputies are scheduled to retire in the next four years. Last week, Joseph P. Sullivan, a deputy since 2017, abruptly resigned.

Armstrong, Outlaw’s friend and former academy colleague in Oakland, said her career there showed that she will lead in her own style.

“She’s never been one to follow. She always did it her way.”

For a few years, he said, Outlaw was his boss and held weekly planning meetings to discuss crime-fighting strategies. She often asked commanders how a proposed policy might impact her sons — a departure from how most cops talk about tactics, Armstrong said.

But Armstrong appreciated Outlaw’s candor, and has no doubt she’ll bring it with her to Philadelphia.

“It’s a victory for those of us in law enforcement who believe we need an injection of new blood,” Armstrong said. “She’s never been one to follow. She always did it her way.”