As a child, Danielle Outlaw was scared of cops.

Growing up in East Oakland, Calif., she was taught to run when she saw a police officer. When she was in middle school, Oakland police arrested her cousin. Outlaw was an only child, and her cousin was like a brother to her.

"The police took away someone I loved very, very deeply for a very long time," she recalls. "You came and created a void in my life, and I don't like you because of it."

More than three decades later, Outlaw isn't just a cop—she's running the Portland Police Bureau. She doesn't look like many of Portland's past police chiefs. She doesn't act like them, either.

The first black woman to lead the bureau is tough-talking, frank, almost schoolyard in her bluntness. In her first year on the job, she's taunted protesters—"you get mad because I kicked your butt," she said on the radio in August—and publicly challenged her boss, Mayor Ted Wheeler, when he asked police to stay away from a protest camp.

"In Oakland, we tell you what we mean and we mean what we say," says Regina Jackson, who knows Outlaw from California. "She's an Oakland girl—a straight talker, a straight shooter. That kind of leadership is a risk, but good leaders take risks."

After one year as police chief, a clearer picture of the 42-year-old Outlaw is emerging. Since the August radio interview, she's grown more cautious in her public statements. According to more than two dozen people who discussed Outlaw with WW—City Hall insiders, colleagues on the police force, and friends and peers from her days in Oakland—Outlaw is a smart, careful, cops' cop who seems less interested in the kind of police reform her boss Wheeler campaigned on than in taking back control of the city's streets.

(Thomas Teal)
(Thomas Teal)

Wheeler hired Outlaw last year because he wanted to show he would make big changes—starting at the top—to a bureau he said badly needed a shakeup.

But instead of reform, she's pushing to put greater power into the Police Bureau's hands by, among other things, forcing protest groups into what are effectively "free-speech zones"—limiting when and where groups may demonstrate.

A newly proposed ordinance the City Council will debate Nov. 8 would give Portland police broad latitude to corral protesters. Two commissioners—Amanda Fritz and Chloe Eudaly—are opposed, and undecided Commissioner Nick Fish will likely be the swing vote.

Outlaw and the mayor's office both say she asked for the change, after August protests spun out of control.

"If we're getting involved where it's already jumped off, it's too late," she tells WW. "At that point, all we have is force. We really don't want to use force if we don't need to. The best thing to do is be strategic and get ahead of it."

The effort to reassert police control over political speech tests how much trust Portland has in her at a crucial time.

Portland's penchant for protest has always made it a hard town to police (that's how we got the '90s nickname "Little Beirut"). That reputation has now made the city a target for political extremists and white nationalists. Since the last election, Portland has seen political violence on its streets unprecedented in scale and intensity.

Is Outlaw up to the moment?

(Sam Gehrke)
(Sam Gehrke)

If you didn't know her and saw Outlaw out of her dress blues, you wouldn't guess she's the highest-ranking cop in Portland.

At 42 years old and standing only 5 foot 4, she's younger and smaller than the average police chief. She keeps her long, meticulous braids pinned to her head while on duty, but off the clock, they fall nearly to her waist. Her arms are inked with tattoos: a Taoist symbol, a treble clef, and a quote from Shakespeare's A Midsummer Night's Dream: "Though she be but little, she is fierce."

Danielle Outlaw’s yearbook photo.
Danielle Outlaw’s yearbook photo.

Danielle Outlaw was born on the rough east end of Oakland, a city with a long history of animosity between citizens and the police. Gang violence, shootings and corrupt cops have given Oakland a reputation as the gritty cousin to San Francisco.

Outlaw's father worked for the state's transportation department and her mother for AT&T. One day, when she was in grade school, Outlaw recalls, she was playing in a plastic pool in the front yard when a man walked by and spat into the water. Her mother decided to move: "And she said, 'That's it. It's time to go,'" Outlaw says.

At 14, she enrolled in an all-girls Catholic high school in the rolling hills of Rockridge—a middle-class neighborhood with few black families. She got into Holy Names High School when the administration ignored counselors who said she "had a problem with authority."

For four years, Outlaw studied in halls adorned with Catholic statues and paintings. She says the school and the friends she made there "probably saved my life."

That same year, 1990, she decided to become a police officer—after the school sent her on a ride-along with an Oakland cop. Her family and friends were baffled.

"No one was saying they wanted to be a police officer growing up," Outlaw says. "People were shocked. My dad told me flat out it was a waste of a degree."

Outlaw stayed in Catholic schools and earned her undergraduate degree at the University of San Francisco, graduating in 1998.

Fresh out of college, she joined the Oakland Police Department—a far less sedate place.

Outlaw worked for OPD for 20 years. During that time, she witnessed some of the worst police scandals in the country.

In 2000, four of her colleagues, known as the "rough riders," were charged with planting drugs on black suspects. They were all terminated, and the city paid victims more than $10.9 million, but the criminal charges didn't stick against the officers. Nine years later, Outlaw witnessed her city's outrage over police shooting black men—including Oscar Grant, who was shot by transit police while lying face-down on a train platform in 2009.

But no case revealed the rot inside Oakland's force like that of 17-year-old Celeste Guap.

In 2015, Guap, the daughter of an Oakland police dispatcher who said she had been working as a prostitute, threatened to reveal that an Oakland police officer named Brendan O'Brien and several other officers were having sex with her.

O'Brien killed himself. Oakland police hid his suicide note and the allegations for months before finally opening an investigation. The criminal cases floundered, ending in dismissals or lenient plea deals. Just one Oakland captain was convicted and sentenced—to three years' probation.

Outlaw was deputy chief as the scandal unfolded. She watched the OPD burn through three police chiefs in a week after Guap's story became public. Outlaw was never implicated in the thorough investigation of the abuse and cover-up that followed.

"When she started, OPD was close to, if not the worst department in the Bay Area, and there were a lot that were not good," says civil rights lawyer Jim Chanin, who made a career suing Oakland police and other law enforcement agencies. "If you used force, you were admired. It must have been very hard to come up with any integrity at all."

Chanin remembers Outlaw as a well-respected officer who worked up the ladder without a scandal. "Being a police officer is not an easy job, and it's even tougher for women," he says. "She had to struggle in that environment, and she did very well."

Outlaw was a beat cop only briefly. She rose through the ranks, eventually becoming Oakland's second female deputy chief and, for several years, the highest-ranking woman in the department.

She served as commander overseeing the records division, the 911 dispatch center, and training. She worked as a public information officer and then as a captain in the internal affairs division.

"I was assigned cases where the hard calls had to be made," Outlaw says. "The one where folks would go, 'Ooh, that would end up on the news.'"

Regina Jackson, who runs the East Oakland Youth Development Center and also sits on the Oakland police citizen review board, says Outlaw was the kind of cop who embedded herself in a community. Outlaw met Jackson six years ago, over a cup of coffee at Starbucks.

Regina Jackson (Martin Thiel)
Regina Jackson (Martin Thiel)

"I had never had an officer try to reach out with no specific problem," Jackson says. "It was pleasantly surprising."

Jackson says she doesn't think Outlaw focused on what she'd call "sexy projects," but took a lot of jobs other officers wouldn't gravitate toward—like internal affairs. "The optics of the jobs she was doing," Jackson says, "they were jobs people didn't want to do."

Outlaw was a lieutenant in 2011, when the Occupy Oakland protests set up camps in the city and refused to move.

One day, Oakland police struck the Occupy protesters with flash-bangs, bean bags and other less-than-lethal munitions, leaving several people with bruises, chemical burns or permanent hearing loss.

The city of Oakland paid protesters $1 million in damages and implemented a number of reforms local civil rights leaders say have drastically reduced the department's use of force on protesters.

"Since the Occupy Oakland demonstrations, Oakland police have dramatically cut the use of flash-bangs," says Chanin. "It's so much better now than six or seven years ago."

Outlaw, who worked in internal affairs at the time, oversaw all of the complaints filed against the Oakland police after the protests.

The lesson she took away from handling those complaints? She says she learned to balance the safety of protesters and the protection of private property.

"We were still of the mindset of 'Just as long as no one gets hurt, we're good,'" she says. "I walked away from that saying, 'OK, there has to be balance.' The merchants also wanted to feel safe. There were a lot of windows that had been busted out."

In Portland, Ted Wheeler ran for mayor in 2016—and said the Portland Police Bureau was the city agency most in need of reforms.

Six months after his election, Wheeler named Outlaw chief. Outlaw says one of the reasons she applied for the job was because she knew the city had a reputation for large, tense public protests.

"A lot of the work had already been done in Oakland, and I was there at the table for it," she says. "I really wanted to make sure my skill set contributed to something where you could see it."

The debate over how Portland police control protests has become the central question defining Outlaw's first year on the job.

(Sam Gehrke)
(Sam Gehrke)

Interestingly, Outlaw authorized the firing of flash-bangs into a crowd of leftist counterprotesters opposing Patriot Prayer during the Aug. 4 protests. A 52-year-old woman suffered chemical burns, and a young man was rushed to the hospital with a brain hemorrhage after being struck directly with a flash-bang—the kind of munitions Outlaw helped phase out in Oakland.

Chanin, the Oakland lawyer, was surprised to see Outlaw giving flash-bangs the go-ahead.

"This was a big deal when she was here," he says. "I thought she learned the same lessons the whole department did."

When WW asked about that contradiction, Outlaw said the use of flash-bangs was under internal review. She added that she wanted as many tools as possible: "We know these events are going to continue to happen and folks are going to continue to test the water."

But this fall, the tensions building around Portland police became national news.

It started with a shooting.

On Sept. 30, officers responded to a 3 am fight in a downtown parking lot. As officers walked toward the scuffle, 27-year-old Patrick Kimmons pulled a pistol and fired five shots into the crowd, hitting two men. Then he ran toward police.

Sgt. Garry Britt and Officer Jeffrey Livingston fired 12 rounds at Kimmons, hitting him nine times.

In an ambulance, another officer held an oxygen mask over Kimmons' mouth as he struggled to breathe. "Don't let me die, bro," Kimmons begged. "I'm gonna die." He died 32 minutes later.

The following Friday, Oct. 5, Outlaw spoke to Kimmons' family and friends in a meeting room at the bureau's North Precinct. It was an unprecedented encounter in the wake of a police shooting.

"I'm a mother first," she said, telling the crowd her 17- and 20-year-old sons were flying to Portland that day to visit. "I couldn't imagine if I got a phone call saying something had happened to my 17-year-old whose flight didn't land or something. I couldn't imagine."

Her voice wavered. "But I need us to get to a place where we recognize we are all community," she said, in video published by The Oregonian. "I live here, too."

(Sam Gehrke)
(Sam Gehrke)

Kimmons' death still set off a chain reaction that has drawn national attention.

A group called Don't Shoot Portland led black-clad marchers through downtown in early October. They chanted, "Black lives matter!" and blocked traffic.

A frustrated driver tried to push through a small crowd of those protesters Oct. 6. As he slowly pushed his car into a man who refused to move, other protesters banged their fists on his silver Lexus.

Fox News and other conservative media outlets seized on video of the confrontation. They accused Mayor Wheeler and Portland police of allowing "mob rule" to take over the city.

Vancouver, Wash., right-wing protest leader Joey Gibson, incensed by the Fox News story, organized a "flash march for law and order" that brought a roving group of Proud Boys to downtown Portland on Oct.13 near dusk. They got into a massive brawl with antifascist protesters—the two sides beating each other bloody as cameras rolled.

The brawl was the last straw for Wheeler. Two days later, he announced his proposed ordinance to give Outlaw the power to make it tough for the Proud Boys and Antifa to fight in his city.

Wherever Outlaw goes, people want to talk to her about how Portland police handle protests.

They tell her police are cracking down too hard on protesters. (During the Aug. 4 protests, leftists screamed insults at her, calling her a race traitor.)

(Sam Gehrke)
(Sam Gehrke)

Or, like the young Trump voter who confronted Outlaw last month, they say cops should crack down more.

Frank George, 19, who leads a conservative student group at Warner Pacific College, pitched a fastball during an Oct. 15 Q&A with Outlaw.

He claimed he had watched police stand by in November 2016 while leftist protesters beat an elderly man in the streets and pepper-sprayed his 70-year-old wife. "And I called out to them for help," George said. "They said no."

Outlaw gripped the back of a wooden chair and swayed.

"We get criticized for doing way too much," the chief answered. "Or we do way too little and we get comments like yours."

She described her frustration with the rules of engagement for cops faced with protesters who arrive with express intent to hurt each other. Her large brown eyes widened when she suggested sending an officer into a crowd of 40 or 50 people.

"Quite frankly, we all want everyone to have the ability to come and express whatever it is they want to express safely. But let me say this: If I send one officer into a group of people maybe this size, and my officer gets caught up in whatever that is, what good did sending my officer do?"

Two hours later, Outlaw stood with Mayor Ted Wheeler at a podium in City Hall—and said they were going to change the rules.

Wheeler introduced an emergency ordinance that could authorize Portland police to place restrictions on when and where people may protest, if those demonstrators have a history of violent clashes. Under the new rules, police would be authorized to tell protesters where they may gather—in theory, allowing them to keep alt-right instigators on one side of the river and their Antifa foes on the other.

(Sam Gehrke)
(Sam Gehrke)

The mayor's office says Outlaw asked for the new rules.

"She was looking for a tool to keep demonstrators with a past history of violence separated," says Berk Nelson, an adviser to the mayor. "People from the far right see it as a violation of their First Amendment rights, as well as those on the far left. But people's speech is being chilled now—and it's not coming from the government."

When Outlaw discusses these policies, her usual directness turns into a focus on granular detail. But she's clear: She wants this rule, because she believes it will keep her officers from having to use munitions like flash-bangs.

"It gives us more teeth," she says, "to make sure we can ensure a safe environment for everyone."

Outlaw is taking criticism from the left and right.

"She uses all this woke rhetoric, but then her police go out and use the same brutal tactics," says Olivia Katbi Smith, who co-chairs the Portland chapter of the Democratic Socialists of America. "I don't give a fuck about what she's saying. What matters is what she's doing."

James Buchal, chairman of the Multnomah County Republican Party, likes that Outlaw criticized Antifa on The Lars Larson Show in August. "I think it showed she had good instincts," Buchal says. "Whether she's allowed to use them remains to be seen. Making the mayor into the free speech kommissar who can make up the rules as they go isn't the right approach."

The police union praises her. Her bond with the union—and its president, Daryl Turner, who is also black—is unusually strong.

Sources close to the bureau say Turner has been forgiving to Outlaw, even when she annoyed the rank and file.

"Daryl Turner has been uncharacteristically positive toward her," says a source close to the bureau. "He is invested in her somehow. He was making excuses for her, which means he believes he has influence with her."

Turner did not respond to a request for comment.

Portland Police Chief Danielle Outlaw. (Cheyenne Thorpe / Multnomah County)
Portland Police Chief Danielle Outlaw. (Cheyenne Thorpe / Multnomah County)

For years, Portland police have had problems. The U.S. Department of Justice in 2012 found a "pattern and practice" of using excessive force on the mentally ill. And growing crime connected to the city's housing crisis has left many Portlanders with little faith in the cops.

But Outlaw's only significant changes in the bureau have been relatively small, or increased the police's power.

She added a new position to the executive leadership team. The bureau won an additional 58 officers when City Hall battled over the city budget. And she has been a champion for putting more resources toward decreasing shootings by reworking the former Gang Task Force to focus entirely on gun violence—a move that is universally palatable and has been done before.

Why hasn't Outlaw focused on more substantial changes?

Sources with inside knowledge of the bureau say Outlaw has been slow to make key decisions, allowing programs to languish and failing to keep promises.

One example: Last December, Wheeler ordered the Police Bureau to alter its policy to tow stolen vehicles so that low-income victims of auto theft wouldn't have to pay hundreds of dollars to get their cars back. The chief did nothing.

Outlaw says she wants to make some reforms, but change has to come gradually, especially because she's an outsider in the bureau.

"If you come in here and say, 'I'm going to change everything all at one time,' you're going to lose people," she says.

The delay in changing the bureau's tow policy is not the only time Outlaw has shrugged off the mayor's instructions. In July, she insisted Portland police sweep an encampment of Occupy protesters outside Immigration and Customs Enforcement headquarters after Wheeler had ordered the bureau to keep the conflict at arm's length. She said publicly she "wasn't asking for permission" when she told Wheeler her officers would intervene.

Occupy ICE (Sam Gehrke)
Occupy ICE (Sam Gehrke)

But the mayor's new reform to keep demonstrators separate has Outlaw's backing. It meets both of their needs for a high-profile win.

Critics on the left and within the bureau suspect Outlaw is already looking toward her next job.

"Some officers have wondered, is Portland just going to be a stopover and then she's going to be moving on," says one source close to the bureau.

It is a criticism Outlaw acknowledges but dismisses. "People are seeing in me something that I'm not even thinking about," she says.

Yet Outlaw certainly has spent a significant amount of time building connections outside of Portland. In 2018, she traveled to Philadelphia, Nashville, Arlington, Va., and even Israel to attend or speak at law enforcement events.

By her one-year anniversary in the job, Outlaw had spent 56 days away from the city, at conferences and out-of-state speaking engagements, according to her public calendar. That's more than 20 percent of her working year out of town. The mayor is aware of the extensive travel, but allows the Police Bureau broad latitude in authorizing the trips.

Her decision not to rock the boat in Portland could help Outlaw land a future job in a larger city.

Pleasanton, Calif., police chief Dave Spiller, who serves a smaller city in the same county as Oakland, agrees she is probably just getting started.

"I suspect her law enforcement career is limitless," he says. "She's just that kind of person. She's experienced a lot in Oakland, and that has probably taught her who she wants to be and who she never wants to be, and she carries that with her."