David Keenan
David Keenan (courtesy photo)

One of the first things that David Keenan did after landing a job as an associate at Orrick, Herrington & Sutcliffe in 2009 was take home a coffee mug with the firm’s logo on it.

He thought it might turn out to be a souvenir—a token from a life he almost had.

“I really was suffering from a bad case of what some people will call ‘imposter syndrome,’” Keenan recalls. “I thought, ‘I’m not going to make it here, but when they find me out and that I’m not Orrick material, at least I’ll have this coffee cup.’”

Things have turned out differently. After rising to become a senior associate in the firm’s white-collar and securities litigation practice in Seattle, Keenan will depart to take the bench on Jan. 9 at the Superior Court of King County, which encompasses the booming Northwest city.

It’s easy to see why Keenan didn’t expect to cut such a path. Unlike most of the attorneys who walk the hallways at white-shoe firms, some of Keenan’s first experiences with the law came in handcuffs before he was a teenager. Now, he’s completing a round-trip of sorts, becoming a judge in the court system where he once was a juvenile defendant.

David Keenan campaigning

During his time with Orrick, much of Keenan’s regular work has consisted of—to use his words—“protecting the privileged.” Among the victories touted in his Orrick bio is a successful defense of Nordstrom Inc. in a shareholder lawsuit over Nordstrom family members’ use of private planes. He also helped defend Barclays in the residential mortgage-backed securities fallout.

But Keenan sees that experience as giving him insight into how the powerful operate in the justice system—a perspective he considers valuable as he steps into a new phase of his career.

“I feel like I’m a more powerful advocate for marginalized communities because I’ve seen it from the inside,” Keenan says. “I hope that’s going to make me a better judge.”

Second Chances

Keenan, whose voice occasionally dips to low, gravelly tones that seem out of sync with his trim, smiley appearance, thinks a lot about second chances. He’s had a number of them.

Growing up in a “prostitution watch area” on the northern end of Aurora Avenue—an unlovely strip of concrete that winds through Seattle—Keenan’s father floated in and out of jail while his mother supported the family on welfare. He quickly fell into a group of kids who got into trouble and missed most of the seventh, ninth and 10th grades. “I was basically out just running the streets,” Keenan says.

When he was 12 or 13 (he can’t remember and the records have been expunged), Keenan was arrested after a fight. He avoided being sentenced to juvenile detention through a diversion program. But Keenan still remembers the waiting area at the juvenile court downtown, hearing his name called, and the vague sense of fear that gripped him then.

It wasn’t his only dust-up. Keenan was last charged with a crime a day after his 16th birthday, and not long after, he dropped out of high school and got at a job at a Jack in the Box fast-food restaurant. His ambitions were limited. “I’m thinking, ‘Maybe I can manage this Jack in the Box one day and make $24,000 a year.’ And there’s no shame in that.”

His path started to turn when a co-worker told him about something called the “Explorer” program, which provides limited police training to youths between the ages of 14 and 21. It’s the kind of thing that the Seattle Police Department advertises when it sets up booths at local fairs. Keenan applied—and was promptly rejected.

His mother called the program’s director and pleaded with him to reconsider. More than 30 years later, Keenan vividly recalls the conversation with the officer, who he met with after taking a bus downtown. “I don’t normally take kids like you,” Keenan recalls him saying. “But every now and then, I take a chance on a kid who I think could go either way.”

Keenan says he thrived in the program. He earned his GED, attended community college and transferred to the University of Washington before taking a job in 1994 with the criminal unit of what was then called the U.S. Immigration and Naturalization Service. Based in San Diego, he worked on drug crimes and human trafficking, and mostly felt like he was putting bad people away.

But there were parts of the job that ate at him. One day, after being transferred back to the Northwest, Keenan was booking a suspect when his partner saw another “Keenan” listed among the inmates. It was a family member, but at the time, Keenan told his fellow officer it was just a coincidence.

“When I see a relative or anybody caught up in my system,” he says, “I just think about the myriad chances where we failed those people.”

Becoming an Advocate

While continuing to work for the federal government, Keenan attended night classes at Seattle University School of Law. In 2007, he took leave to work as a summer associate at Heller Ehrman, only to see the firm—and his job offer—implode when the firm filed for bankruptcy in 2008.

Instead he landed at Orrick.

“I get the sense that Dave wakes up every morning grateful for everything he has,” says Daniel Dunne, an Orrick partner who joined the firm from Heller in 2008 and helped clear a path for Keenan. He recognizes “that there is precious little difference and a whole lot of luck that separates the very successful from those who are struggling,” Dunne adds.

In addition to his law practice, Keenan has been involved with community and legal organizations, including the “180 Program,” which allows juveniles to avoid criminal charges pre-filing by performing community service or going through counseling. While there has been much debate about how to confront mass incarceration, Keenan believes there should be more done to keep people out of the system from the start.  “I am very much a root-cause kind of person,” he says.

He also speaks bluntly about the societal forces that he believes allowed him the chance to make a different life: namely, the fact that he is white. If not for that, he says, his fate might have been different. The numbers would seem to support that thinking. King County is less than 7 percent black, but African-American youths are five times more likely than whites to be referred to the juvenile justice system, according to census data and a presentation prepared by county court judges in 2015.

Keenan’s perspective is also shaped by his 11-year-old daughter who is mixed-race (her mother, from whom Keenan is divorced, is Asian-American). “The civil rights issues that I work on as a straight, white male are more consequential for her,” he says.

Full Circle

To the extent that Keenan had a plan for his career, becoming a judge had not been a part of it. But after seeing the justice system from its various angles—as defendant, enforcer and advocate—he says he began to wonder if the bench might be the best place to help people who grew up like him.

He had a little prodding. The person who first urged Keenan to consider the judiciary was Steven Gonzalez, a Washington State Supreme Court justice. The two had known each other since when Keenan was in law enforcement and Gonzalez was an assistant U.S. attorney.

“I think it’s really important to have people on the bench who have real-world experience, compassion and some depth of thought,” Gonzalez says. “You don’t want everybody from a corporate background, and you don’t want everyone to be from the U.S. Attorney’s Office.”

Keenan wasn’t uncontested for the judgeship; his opponent was a local solo attorney named John O’Rourke. But Keenan ran a strong campaign, securing endorsements from the entire state high court, The Seattle Times editorial board, and the local alt-weekly, The Stranger (which gave him extra points for dressing up as Ruth Bader Ginsburg for Halloween).

Keenan’s first assignment will be to the general court calendar, adjudicating both criminal and civil matters, at the Maleng Regional Justice Center in Kent, Washington, south of Seattle. But where he hopes to end up is back at the Juvenile Court in the city’s downtown. It’s not a job that most judges covet.

For Keenan, it’s a place where he can pull all of his experiences together. He says that a lot of what judges do is rote, calling shots based on agreed recommendations or sentencing ranges. But not always.

When the call is harder to make, judges have to tap their well of personal experience, Keenan adds. “And I feel like I have a lot to draw upon.”