The Complicated Mystery That Is Danielle Outlaw

Through two tumultuous years, Outlaw — statistically minded, coolly professional, able to speak in perfect sound bites — has perplexed and infuriated a city that expects a crusader as its top cop. Hamstrung by COVID and controversy from day one, can she ever connect with the city—and fix the department she was hired to reform? 

Danielle Outlaw arrived in Philadelphia two years ago to much fanfare. But her tenure as police commissioner has been challenging. / Photograph by Colin Lenton

It’s a balmy fall afternoon in the middle of evening rush hour at Broad and Olney — one of the city’s busiest transit hubs — and I’m waiting for Danielle Outlaw as three horses and their urban-cowboy riders saunter past.

“They were just in the Wendy’s drive-thru,” East Police Division inspector Michael Zimmerman tells Community Relations Division commanding officer Jarreau Thomas, sharing a laugh about the vagaries of Philly street life.

Thomas, like many officers of color, is a first-generation cop — and the youngest inspector in Philadelphia’s policing history. Zimmerman, like many white officers on the force, is a cop’s son, with 17 years on the force. But he has also doubled as an academic; he was once an adjunct instructor at Rosemont College and has a master’s degree in homeland security. They represent the next generation of Philly’s top cops, the embodiment of a mind-set shift from cop-as-warrior to cop-as-community-guardian that police forces across the country have struggled to make post-Ferguson.

I’m here with them because they’re the officers that Danielle Outlaw, Philadelphia’s polarizing police commissioner, wants me to see. I’m waiting here with the neighborhood brass after spending months chipping away at the thick PR wall that’s gone up around Outlaw since she reported for duty in early 2020.

She started her job with much fanfare, arriving from Portland, Oregon, to become the first Black woman to lead Philly’s force. She was tasked with cleaning up in the wake of numerous departmental scandals, from the mishandled sexual harassment claim that toppled the former chief, department lifer Richard Ross, to the 300-some officers found to be posting racist content on social media.

But not long after Outlaw, 45, started, she found herself in a crucible of COVID, fury over her department’s violent response to protests, and anguish over the police killing of a civilian. In the span of a few months, she went from being the subject of adoring think-pieces about her hairstyle and fingernails to having major media outlets call for her resignation. Before she got to set her agenda — before we got to know who she is as a cop, as a person — the world fell apart, and we all retreated to our bunkers.

Yet two years later, despite all the bad press — and a flurry of December rumors that she was about to become New York City’s top cop — Outlaw is still here. She seems, improbably, to have weathered the storm, but I wondered whether she could salvage what remained of a tenure that got off on the wrong foot and just kept going.

She was brought to the city to be an outsider — to bring new perspective and a critical eye to a police department in need of reform. During her long career, she’s built a specific set of tools to do just that: a polished exterior, a reliance on data, a refusal to get riled up in the face of criticism. But are those same skills preventing her from breaking through in Philly? Or is Outlaw just in an impossible position during impossible times?

In other words: Is her academic, stats-based approach to policing anathema to a force forged in the scappo il capo — “break their heads” — mold of Frank Rizzo? Or is it possible that in the 21st century — the era of defund the police, culture wars over whose lives matter, and increasing national commissioner churn — Outlaw is maybe the most we can hope for from a big-city commissioner: a yeoman chief who’s affable but guarded, able to absorb a raft of shit from both the right and the left and do so without being actively sexist and racist?

My initial ask was to shadow Outlaw for a day, then sit down with her to pose questions: What have you learned from the gauntlet you’ve been through? How do you respond to your many detractors? Do you have a big plan for gun violence? And, real talk, who are you? Because we still don’t know. She seems borderline irritated talking to reporters. Her responses in press conferences tend toward terse bureau-speak, as if she’s trying to answer the question and make her escape as quickly as possible.

Her media people kept me at arm’s length, but after weeks in which I tailed her from public event to public event, they offered this — a chance to walk around with her for an hour. Just me, Outlaw, a bunch of cops, and thousands of SEPTA riders.

The sunlight has begun its slow slump beneath the horizon when, finally, she drives up, exits her black Tahoe, and apologizes for running late. It’s quickly apparent that this isn’t the buttoned-up Danielle Outlaw of pat answers and strained denials we’ve seen on TV. This version oozes energy and charm. And you can just make out the fascinated whispers among the stunned pedestrians here who slow and stare — Is that her?

We inch our way down Olney Avenue, because she listens to anyone who wants to talk. One of Outlaw’s big goals, she’ll later tell me, has been to humanize the people behind the badges. She’s looking to undo a half-century of policing philosophy that said professionalization meant minimal fraternizing between cops and the public, thus creating an us-vs.-them dynamic in the neighborhoods they patrolled. She uses public moments to try to show that cops aren’t undifferentiated pieces of that thin blue line.

I saw you on TV, so many people say, amazed to glimpse Outlaw in the flesh, and she always jokes back — well, maybe it isn’t a joke — “Don’t believe the bad stuff, ha-ha-ha.”

Danielle Outlaw’s journey to top cop here seems unlikely when you consider where her life started. Danielle Bowman was born in 1976 in Oakland, California, a national hot spot for police brutality. As a girl, she inherited a disdain for the Oakland police department that ran deep in Black and Latino communities. “No one was saying they wanted to be a police officer growing up,” Outlaw once told a reporter.

Her mother, Barbara Bowman, expected her to be somebody.

“When I was around five years old, my mother gave me a typewriter,” Outlaw told a group of middle-school girls at the Positive Image Youth Girls Summit at the PAL on East Tioga Avenue in Harrowgate in November. She was delighted by the gift, set the typewriter up, started clacking away, then announced that she was going to be an office worker when she grew up. But Barbara was aspirational and shut down that talk. She wanted her only child to aim much higher.

Though the pair lived in Oakland, Outlaw says Bowman used her parents’ Berkeley address — her father was a food worker and her mother a janitor at UC Berkeley — to enroll her daughter in that city’s highly rated public-school system. Later, Bowman had another idea — a pricey private Catholic girls’ prep school, Holy Names High. Outlaw was neither well-to-do nor Catholic, so it took some doing to get in — and once she was in, she had to take four buses to get there. She barely passed the interview process, because while her test scores were off the charts, her grades were atrocious. (The problem, she told the girls at the Harrowgate PAL, was that “I had a stank attitude.”)

Outlaw credits Holy Names with polishing her outsider’s rough edges and putting her on the road to success. And perhaps that experience made possible what came next: When she was 14, on a friend’s dare, she signed up for a two-week high-school career exploration experience in which she got to shadow a police officer. It so changed her perspective that by the time she got to college, she was already part of Oakland’s Police Explorers, a cadet program.

Outlaw earned her BA in sociology from the University of San Francisco, but by then she had a baby on the way, and her dream of an advanced degree would need to wait. Not long after giving birth, she took the fitness test, passed, and entered the police academy. On the academy’s Family Day, her disappointed father told everyone — recruiters, trainers, relatives — that his daughter had completely wasted her college degree.

Danielle Outlaw as a cadet in Oakland. / Photograph courtesy of Danielle Outlaw

Over the next 18 years in Oakland, Outlaw would steadily work her way from patrol officer to chief deputy in charge of bureau services, earning a master’s degree in business administration from Pepperdine University in 2012. As deputy chief, commander of the Bureau of Risk Management, Outlaw oversaw the Training Division, the Internal Affairs Division, the Office of Inspector General, and the Criminalistics Division under Oakland police chief Sean Whent during a period of reduced crime. Eventually, this career trajectory would become fodder for her detractors. “During her four years as a sergeant, she worked in patrol for a minute and then transferred to Internal Affairs,” writes one anonymous blogger who chronicles the inner workings of Philly’s police department. “She then became lieutenant after another minute in patrol.”

Still, someone a bit distanced from the rank-and-file was maybe just what Mayor Jim Kenney, who is reviled by the Fraternal Order of Police, wanted in late 2019 to shake up a department that had been rocked by scandals of sexual harassment, racism and ineffectiveness. “Make no mistake: While I have tremendous respect for our officers, the Philadelphia police department needs reform,” Kenney declared on December 30, 2019. “I am appointing Danielle Outlaw because I am convinced she has the conviction, courage and compassion needed to bring long-overdue reform to the department.”

Danielle Outlaw arriving to her introductory press conference in Philadelphia in December 2019. / Photograph by Monica Herndon / The Philadelphia Inquirer / Associated Press

He’d chosen Outlaw from a pool of 33 candidates, bringing her here from Portland, where in 2017 she’d been named the first Black woman to head that city’s 1,000-member police force. (Philly’s force has about 6,000 members.)

The point of the outsider police chief is to send a very public signal — business as usual is no longer accepted — in order to restore public trust. However, an outsider has a steep learning curve. Outlaw needed to find an executive team she could trust, gain a deep understanding of the politics of the community, connect with elected officials and news media, and make the rank-and-file feel heard. On top of it all, she had to make a significant difference in a short period of time.

But between his announcement of her selection and the day Outlaw started, Kenney watchers say, the Mayor, disgusted by the messes of the police department, had already disengaged, leaving Outlaw on her own to struggle with cleanup while he battled the pandemic.

She admits to me during one of two walk-abouts we do that she feels she lost a year of getting to know Philadelphians, between COVID and the civil unrest. She says she’s just now — two years into her tenure — beginning her onboarding process.

“She started with three strikes against her — she’s a woman, she’s Black, and she’s from the outside — and some people can’t get over those issues,” says Phil Goldsmith, former managing director during the John Street administration. Add the other challenges of this unsettled era, and, Goldsmith muses, “I can’t think of a worse time to be a police chief.”

It has, indeed, been the worst of times.

Outlaw started on February 10, 2020. Governor Tom Wolf announced a public health emergency on March 6th, and every aspect of police work had to be rejiggered. A week later, Corporal James R. O’Connor IV was shot to death as he was serving a murder warrant in Frankford — the first Philadelphia cop killed in the line of duty in five years, and only the second time in Outlaw’s career that she had to deal with a fallen officer. She would present five more fallen-officer flags that year, all to the families of victims of COVID.

Then came the national unrest following George Floyd’s murder by a Minneapolis police officer on May 25, 2020. For days, peaceful protests and violent looting intermingled, especially in Center City. It boiled over on June 1, 2020, when police fired tear gas into a crowd of protesters who were illegally but peacefully marching on the Vine Street Expressway during rush hour. (Police also used tear gas in residential parts of West Philadelphia and in Kensington.) A month later, the New York Times published a damning second-by-second video of the Vine Street confrontation, and hell broke loose anew. At least 100 cities used tear gas that summer to curtail rioting, but it was Philadelphia that became the poster child for excessive force. Condemnations came from as high up as the United Nations.

Police officers respond to the George Floyd protests in Philadelphia. / Photograph by Matt Rourke / Associated Press

Outlaw responded to the crisis with her signature polished, unflappable bureau-speak. She first told the press that tear gas was selected because “other options were not effective,” a claim countered by state police radio communication from the event. Then she said the decision was based on bad information, but only after the New York Times video went viral. The Inquirer editorial board called for her head: “Over the course of three days and many bad decisions, the police created chaos and danger instead of delivering order and safety. There is no more profound law enforcement failure than that. There is no simpler rationale for the mayor to ask the police commissioner to resign.”

She survived, but her reputation didn’t. A SWAT officer who’d pepper-sprayed a protester was fired. Managing director Brian Abernathy, who was responsible for the city’s operating units, including the police, was ousted and replaced by Tumar Alexander. Mayor Kenney came to Outlaw’s defense, feebly, at an awkward press conference during which deputy commissioner Dennis Wilson, the incident commander, claimed full responsibility and took a voluntary demotion to chief inspector.

Yet what’s happened since has been perhaps even more frustrating. Every other week since March, the PPD has held a gun violence briefing. Outlaw and her team report on Operation Pinpoint — the data-driven strategy, started under her predecessor Richard Ross, that concentrates resources in the most impacted areas. There’s evidence this is lowering crime in hot spots — but that’s been little relief in a city with a murder rate that seems to defy gravity, and the media has been unmoved.

Danielle Outlaw speaks to the media in the aftermath of Floyd’s killing. / Photograph by Tim Tai / The Philadelphia Inquirer / Associated Press

The bad press has frustrated Outlaw, who argues that no police chief can combat what is a national increase in gun crimes. “A win is a win is a win,” she’s said, “and at any time when there’s optimistic info or a chance to point out one thing is working, or persons are arduous at work, we now have to offer individuals their kudos for that.” But it’s hard to stand numbers up against the mounting stories of teenagers shot down in their prime or the shots of grieving mothers on Action News.

After we wrap up our walk at Broad and Olney, I tag along with Outlaw to Martin Luther King High School for a community listening session about gun violence, organized by State Representative Stephen Kinsey. Keisha Wilkins, head of the 551-student school, has said that 30 young adults with connections there have been murdered during her six years as principal. The idea for the night is for the community to provide solutions and the city leadership to listen.

It’s a large crowd, and many people want their two minutes at the mic, but rather than solutions, there’s a cacophony of parenting tips, complaints, self-promotion, and personal testimony. It was settings like this, Tom Junod wrote in 2000 for Esquire, that helped former Philly police commissioner John Timoney, who’d come here from New York at the behest of then-mayor Ed Rendell, move from outsider to beloved insider. His energy levels were legendary, and he piled on the community events:

People stand up in full hue and cry, abandoned auto this, abandoned house that, and the commissioner, he never says, We’re trying or We’re doing our best, no, he says, “See that man over there? That’s the captain of your district. You talk to him after the meeting and I guarantee that that abandoned house will be sealed up and won’t be used as a drug house anymore. You talk to him after the meeting and I guarantee you that 1979 Chrysler Cordoba will be gone by Thursday.

The MLK High School listening session drones on and on and on. At some point, long before it ends, Outlaw slips away.

The next time I’m with Danielle Outlaw, we’re at the Arrott Transportation Center in Frankford on a frigid November afternoon. Outlaw tells me she wanted to make time for us to talk, because it hasn’t happened yet. She says I’m the only reporter who has followed her like this. By now, I’ve spent hours on her trail at public events and watching her work a crowd. Her interest, if I’m being honest, makes me feel special. Note to self: Charm disarms.

Here in the Northeast, there are requests for selfies and thank-yous and car honks, too. But that isn’t all there is. There’s also a worried store owner who runs across the avenue. He wants to know one thing: “Will there be rioting?” The verdict in the Kyle Rittenhouse case has just been announced, and the jury found him not guilty. Outlaw listens carefully, explaining that she can’t be certain but reassuring him that the police department is standing ready.

Another resident wants to know why police are treating white men like him unfairly. Another wants her to attend his neighborhood Thanksgiving luncheon that’s coming up in a few days. Still another wants her at a march for missing children. It will always be another, and another, and another thing — complaint, request, demand. Mayors often sell us their choice for police chief using a superhero narrative, and we buy it looking for someone to wipe out our problems. But that means lingering issues are kryptonite, and chiefs are left to manage our expectations.

As we walk up Frankford Avenue, Outlaw tells me about her family, its New Orleans roots, her aspirational mother who died from complications of diabetes six years ago, after the commissioner spent years as her caregiver. I’ve been researching her life. She’s the youngest police chief in recent memory in Philadelphia, and one of the first police chiefs in the social media era. Everything she’s uttered is already documented on the internet. Every question I can think to ask, she’s already answered. Yet, or perhaps because of that, she still feels like an unknown.

At the end of the walk, we wind up at a diner. It’s the first time she seems even a bit weary. “My face don’t hide nothing,” she jokes. We sit, her back against the wall so she can survey the entire establishment. Her tiredness makes her appear younger and more vulnerable. Sometimes, Barbara Bowman would tell her daughter, “I love you, but I don’t like you right now.” Being the police commissioner in Philadelphia has taught Outlaw the meaning of her mother’s words.

We chat — just mom stuff at first. She talks about how the pandemic has affected her sons, ages 23 and 20. She calls them her mini-me’s — one is artistic, like she is. (She once considered becoming a singer.) The other is an athlete. One has flourished with online instruction in college; the other hasn’t.

When you sit across a diner table from her, it’s hard not to like Danielle Outlaw. She’s funny, irreverent, smart. The kind of person you want to hang with. You may hate on her because she looks younger than her age, is petite with a sista’-girl glam thing going on and, yes, that black fingernail polish.

But she’s the police commissioner, and the issue for her isn’t likability. It’s: What will she fight for? Outlaw is nuanced and deliberative in a city that is, in her own description, “very passionate, raw and unfiltered.” We want tales of heroism, conviction and devotion; she brings us statistics and that bureau-speak.

I was raised in Strawberry Mansion when gang fights were legend there. Massive numbers of teen boys would meet at various corners and beat and stab the shit out of one another. Anybody who could move out did; the rest of us survived. My mother’s rule was: Don’t start a fight, but don’t run from one, either. I learned that you had to decide quickly whose team you were on, who the enemy was, and which battles were worthwhile. I raised my boys with the dictum “Don’t be the easy prey.” The front line has its own rules, and the first is, there’s no such thing as neutrality.

For Outlaw, neutrality is a virtue. “I am a public servant. I don’t get to make decisions. I have to be neutral. I am in the forefront; I do have a seat at the table,” she says, adding, “I have to be politically savvy.” She explains that she has to make certain the lines don’t get blurry, that police — and she, especially — stay objective, because not doing so can give rise to a culture of corruption.

The problem is that her professional neutrality can feel like personal detachment. We’re a city that erected a statue to Rocky, a fictional, barely literate character, because he’s a scrappy, never-say-die fighter willing to put his body on the line for his beliefs. As I sit across from Outlaw, so collected, so composed, I can’t help wishing some of that 14-year-old stank attitude that challenged the status quo at Holy Names High still existed, because it feels like Outlaw is carrying a sociology textbook to a knife fight.

When we finally get down to really talking about her tenure here, the situation she’s been handed, the headlines she’s created, the worst epithet she’ll sling at her detractors is … “confirmation bias,” as in, she thinks people critical of her suffer from it. I never get a sense that there’s an issue or a position for which she’s willing to risk her perfectly crafted image — an erudite, personable woman with impeccable credentials.

She doesn’t do well on the ugly front lines, with her position proudly marked. Yet that’s what everybody is demanding of her, which leaves her trying to manage our escalating expectations. “It’s a lot thrust on one person,” she tells me. “Gone are the days that a police commissioner could be good at one thing. I cannot just address the [homicide] crisis. … You can’t just put me in a box. I bring a different perspective. I know what it is like to live in fear of the police. You can be for law and order and reform and accountability. There’s a time and a place for everything.”

So, what do you finally ask the police chief after months of following her around, hours of reading her backstory, and then weeks of wondering if the rumors she might decamp to New York are true? What’s left to say? Especially when current bets are that Outlaw won’t be retained by the next mayor, whoever that may be, and that we’re likely closer to the end of her tenure than the beginning?

According to data from the Police Executive Research Forum, one in four police-chiefs jobs typically turns over every year. But Laura Cooper, executive director of the Major Cities Chiefs Association, told CNN in October that the turnover rate has increased in the past two years. And the typical chief’s tenure, which used to be three to five years, has been getting smaller. The calls for changes in policing are leading to churn. In November, Burlington, Vermont, halted its search for a new police chief because of a limited number of applicants that included no women and a salary offer that was evidently much too low. Jersey City just hired a new police chief who isn’t even a police officer. This may be a sign of what’s to come.

Danielle Outlaw with her family upon being promoted to sergeant in Oakland. / Photograph courtesy of Danielle Outlaw

The truth may be that no single police chief, insider or outsider, can save us. Public safety is complex, problems linger, and even the most charismatic leader can’t bring about change by herself. There are no easy answers. The only thing I can think to ask Danielle Outlaw, the only thing I haven’t seen her address, is how a big-city chief’s performance should really be measured. As always, she has an answer in the form of a list: Are the police responsive? How did they treat you? Does the department have the ability to identify patterns and track them? Does the department embrace diversity, equity and inclusion? Later, Kenney, when I ask him in early December, adds to the list: What are the opinions of neighborhood leaders? Are reforms being introduced? This, they say, should form her real progress report card.

“I think she is doing a great job,” Kenney says. He remains unchanged in his position that an outsider, and particularly a Black woman, was needed to shake up the insularity, misogyny and other ills that had found a resting place in the police department’s culture. He blames the homicide rate on the state’s lax gun laws but points to another stat — the more than 6,000 guns police took off Philly streets in 2021, about 10 percent of which were ghost guns — to justify his upbeat report card. Kenney says if he gave her a grade, it would be an A-minus.

After Outlaw’s second year in Portland, the mayor there, Ted Wheeler, gave her the best marks she could get on her evaluation. He called her “a tremendous asset’’ to the city, an excellent public speaker with good instincts, a “superb representative of the bureau and the city, willing to challenge the status quo, learn and adapt and use data to drive police enforcement.” A few months later, she was gone.

As she and I walk along Frankford Avenue, shivering in the cold, Outlaw says she thinks people want her to be not just the police commissioner, but a public figure and a politician. The comment shocks me, because more than a community celebrity, she is a politician and a public figure. She likes to tell people that she leaves “politics to the politicians.” But changing policing is inherently a political act. Sometimes that looks like schmooze, and sometimes it looks like Frank Rizzo’s theory of scappo il capo. Outlaw shrinks away from this, but the problem is, if you don’t know how to fight, you won’t know how to keep the peace.

Wheeler’s evaluation in Portland continued with a piece of advice that still resonates: “This position is inherently political, not in a partisan manner, but in the sense that it is under public scrutiny and maintaining public trust is done in a political environment. You have good instincts and judgment already, but learning more about political history and relationships in Portland is important to being successful in the position in the long term.”

Yo, Commish — it’s important in Philly, too.

Published as “Is Danielle Outlaw Philly’s Best Hope?’” in the February 2022 issue of Philadelphia magazine.