What 40 years of helping homeless people in Seattle has taught the head of Operation Nightwatch

On his very last day as head of Operation Nightwatch, the Rev. Rick Reynolds told stories.

Stories of a last-minute Christmas delivery to a homeless family; of pushing a broken-down car down the street during a night of outreach; and the time he made someone unhappy while serving a free meal and got a hot cup of clam chowder thrown at him.

Wearing a blue flowered Hawaiian shirt with his black and white clerical collar peeking above the neckline, Reynolds, or “Pastor Rick” as many know him, reflected on Seattle’s homelessness crisis and the role he’s played in trying to do something about it.

He took over the small but nimble faith-based organization in 1994 after serving as pastor at Seattle Advent Christian Church. Before working at Nightwatch, he volunteered with the organization for a decade, doing street outreach largely to patrons of old dive bars around downtown Seattle, many of which are gone now.

For nearly 40 years, he’s either worked or volunteered for Nightwatch, trying to help some of Seattle’s poorest neighbors get more of the things they need, like a hot meal, a warm place to sleep or new, dry socks. During that time, he’s watched the city’s homeless population snowball.

In 1996, Reynolds and a team of volunteers counted 485 people sleeping outside in Seattle’s downtown core. The last point-in-time count in 2020 showed more than 3,700 people were living unsheltered in Seattle.

Under Reynolds’ leadership, Nightwatch’s budget has grown from $75,000 to around $1.8 million. The group conducts regular street outreach, offers free meals and connects people with overnight shelter nightly, and provides permanent affordable housing for up to 24 seniors.

Reynolds turned 69 on May 31, the day before he retired. He isn’t tired from the work. Or even tired of Nightwatch. “I’m just tired,” he said.

Reynolds said he’s thinking about turning some of his stories from decades spent working in homelessness into a book. But for now, he’s shared a few, and some of his lessons learned:

1. “Every obstacle will rear its ugly head.”

While going out on the streets (something he did at least once a week the entire 28 years he worked at Nightwatch), Reynolds met a man he knew was old enough to qualify for the program’s single-room-occupancy housing, for seniors 62 and above. But he didn’t know how much of an odyssey getting him into housing would be.

At first, the man wanted to wait two more years – surviving outside in the meantime – so he could qualify for larger Social Security checks before moving in and paying for the subsidized room (today, the rooms cost between $275 and $300 monthly).

“You know you’ve got to apply [for Social Security],” Reynolds told him, after the two years came and went. “The money doesn’t automatically come to you.”

But the man didn’t have ID, so they had to start there. Reynolds took him to a social worker. There they realized that the name on his birth certificate didn’t match the name on his Social Security card.

He was a veteran, so someone must have put two and two together at some point, Reynolds thought. They went to the Department of Veterans Affairs for help, knowing that a federal ID would make it easier to get Social Security and a state ID.

The entire process took months. Working in homelessness, Reynolds said, “Every obstacle will rear its ugly head at some point.”

Reynolds remembers the moment his friend finally got what he needed:

“He’s standing on the sidewalk with his gleaming, hot VA card picture ID and he goes, ‘I am somebody.’ ”

2. “We don’t have an answer.”

Reynolds remembers one night, around 25 years ago, when a group of Microsoft employees volunteered, helping serve the nightly free meal.

One of the volunteers recognized two women standing in line for food and shelter. He said they both worked for a contractor, providing food service at one of Microsoft’s Redmond buildings.

“It’s not just that our social-service system is broken. It’s that we don’t have an answer for the gap between whether a working-class person can make it with the cost of housing,” Reynolds said.

“It’s impinging on the middle-class people now, so we’re really aware of it,” he said.

“But it’s been this way for a long time.”

3. “Our job is to get over ourselves.”

When Reynolds took the helm at Nightwatch, replacing original Executive Director Norm Riggins, he said he was “just full of myself at the time.”

Early into his job, Reynolds said, there was one guy who often showed up in the evening, hopeful that Nightwatch could get him into overnight shelter. The man struggled with substance use, Reynolds said. He had a tendency to get loud and out of control. And Reynolds said shelters would call and say, “Hey, we love Ronnie, but don’t send him ever again.”

Finding shelter placements for him became harder, but Reynolds remembers one night when Ronnie looked happy because he had a shelter slip in his hand.

“Pastor Rick, ain’t I beautiful?” Ronnie asked him.

“Not really,” Reynolds thought, but he had to lie.

“Yeah Ronnie, you’re beautiful,” Reynolds said he told him. “I figured I’d done my pastoral duties for the night.”

But Ronnie went one further. “Then hug me,” he told the pastor.

Reynolds tried to throw one arm around his shoulders, like a buddy hug, he remembers. But Ronnie reached down, inches taller than Reynolds, and threw both arms around him. The two men were pressed cheek to cheek.

“He gives me a kiss and off he goes,” Reynolds said.

Reynolds’ bubble of self-aggrandizement burst that night thanks to Ronnie, he said. He realized later that he was being the ugly, judgmental one.

“Our job is to get over ourselves and figure out how we can love that person from the heart. Not just tolerate. Love.”

4. “Nobody’s beyond hope.”

Reynolds met a man one evening who was waiting in line for food and a shelter placement. He was inebriated and told Reynolds he’d recently fallen out of his ninth recovery program for alcoholism.

“Holy cow, he’s perfect Nightwatch material,” Reynolds thought. Because Nightwatch is a small organization that largely runs on private donations, it can accommodate people other organizations might not be able to work with.

The man moved into one of Nightwatch’s affordable SRO units. It was destroyed in just three months, Reynolds said, because his drinking was so out of control.

While living there, the man fell down and cracked a vertebra. Reynolds said when the man got out of the hospital, he never drank again, as far as he knew.

He started volunteering and found a job at a local food bank. Eventually, he was able to fully retire on the Olympic Peninsula.

“Nightwatch says: Nobody’s beyond hope if they’re still breathing,” Reynolds said. “He was a wonderful man.”

Working in homelessness isn’t easy, but handing someone keys to their own place is an unbeatable feeling, Reynolds said.

On his last day at Operation Nightwatch, Reynolds paid a visit to one of the organization’s newest senior residents. Before the resident got there, he was sleeping in a tent. Reynolds connected him to Nightwatch’s housing coordinator. He’s in his early 70s, Reynolds estimates.

“I knocked on his door and I said, ‘I’m so glad that you are here and not living in a tent. And I hope you have a long tenancy.’”

And then Reynolds walked through Operation Nightwatch’s doors, handed over his keys and went home.