Leading With Hope

Portland Police Chief Bob Day draws from his own experience of loss to inspire hope for the city’s future By Rachel Brumfield

Bob Day (B18) doesn’t take the main highway into work. Instead, he often drives the side roads, remembering the calls he’s taken over the years. With the police radio on in the background, he reflects on where he’s been and why – 34 years after being sworn in as a police officer – he’s still serving the city of Portland.

Day started his career in law enforcement in 1988 and joined the Portland Police Bureau in 1990. He worked his way up the ranks from sergeant to lieutenant, captain, commander and finally deputy chief before his retirement in 2019.

Then last fall his passion for the city propelled him back to work, to serve as Portland’s new chief of police.

“I love the city of Portland,” he says. “I care deeply about this community. I’ve served here for nearly three decades, so I’ve put a lot of blood, sweat and tears into it – literally.”

It’s no secret that Portland has had a rough past few years. From New York Times headlines to the worsening fentanyl crisis, many might view the situation as hopeless. But Day’s own experience of loss has given him new eyes to look for hope where others might not.

“I’m here because of a sense of purpose and a desire,” he says. “There is a great deal of uncertainty ahead, but I would rather be engaged and pressing into that than waiting to see what happens.”

Day brings decades of leadership experience. Even before serving as deputy chief, he had led large-scale events, encountered critical incidents and faced numerous challenging situations throughout his career. He received his bachelor’s degree in organizational leadership and management from George Fox in 2018, and spent his brief retirement consulting on key issues like behavioral health, public safety and policing for the mayor’s office, as well as leading workshops and keynotes for his consulting company, Reluctant Change.

But it was a particularly painful season in 2016 that shaped his perspective as a leader.

That year, Day was part of an investigation into the unethical behavior of his boss, and was reassigned in a very public transition. Though his name was cleared, the experience shook him.

Then, his 15-year-old son, Sam, passed away after a six-year battle with cancer.

“Losing Sam cracked me open in a way that I wasn’t prepared for,” Day says. “It really challenged a lot of how I saw the world, how I showed up, what I valued and believed in.”

“All of the hurt in that season reminded me of the fragility of all these things that we put our identity in. It prepared me with a different attitude and understanding of what I want to be about and how I want to show up as a leader. It’s given me a great deal of empathy for others.”

He remembers a pivotal moment, early in his son’s diagnosis. He was standing in the kitchen with his wife, uncertain if he had enough faith that God would heal his son.

“My wife said, ‘I don’t think faith is believing God will do what we ask. Faith is believing God will be who he says he is. He says he’s merciful, says he’s gracious, kind and forgiving,’” Day recalls. “And that’s how God showed up. We decided we were going to live with hope.”

Together, their family pursued treatment for Sam all over the country, meeting with doctors in Dallas, Houston, Seattle and Santa Monica, California. To them, hope wasn’t naive optimism about the future, but having something to strive for.

“Even though we lost Sam, we don’t regret ever living with hope,” Day says. “Hope is active. Hope is moving toward a goal. It was so much better than sitting around and waiting to see what was going to happen. It created energy and momentum for us to take risks and seize moments when he was healthy, and when he wasn’t, to manage and make the best of it.”

Now, Day is taking what he’s learned about resilience and hope to Portland. Stepping away from the profession for four years gave him space to see things in a different light. He’s well aware of the challenges the city faces, but he’s more prepared than he’s ever been to lead with hope.

“I entered into conversations and relationships that I never would’ve gone to as a police officer – places of great uncomfortability, dissidence and difficulty – and made myself curious and available. Building on some of those things that I learned when I was in the program at George Fox, it positioned me to be able to come back.”

As police chief, he is challenging his staff of over 1,100 to move forward with hope and be a part of something significant for the region.

“We have a responsibility as public servants,” he says. “We’re part of this community. Our actions impact the community and the community impacts us. Why not be a part of the solution, whatever that might be?”

Day has ambitious goals for the bureau, including transforming the dynamic between the police and those they serve, for starters. But he says in all the years he’s been connected to Portland, he’s never seen such a combination of effort and resources to help the city move forward.

“The community as a whole – whether it’s elected leaders, business leaders, people in marginalized communities – we’re poised to tell a different story,” he says. “We’re moving toward that goal. A year from now, why can’t we be a story of resilience and strength?”

To some, that might seem like blind optimism. But Day has been around long enough to know the difference.

“I have experienced that, even in the midst of sorrow, there can be joy and opportunity.”