– By Taylor Zajonc

I put Keith Wilson’s campaign kickoff on my calendar but expected to skip it. Saturdays are hectic at best, and sitting for a political speech was a tough sell to my all-gas-no-brakes three-year-old.

I’d first heard about Wilson from a BikePortland piece, and I was intrigued. A trucking executive who’d staked his company on green tech before soft-launching a dark horse mayoral run with a group of bicycle advocates? Even for Portland, it seemed like a stretch, but I had to find out for myself.

With an hour to kill, I told my kid we’d visit the Charles Jordan Community Center playground if he put up with a few minutes of the event. He agreed, so I plopped him into the back of my cargo bike, and we took off for New Columbia.

I slipped in a little late, found a spot in the back of the gymnasium, and held my son up so he could see the speakers. He was soon more interested in the refreshments table than the show, so I let him raid the fruit tray while I listened.

It didn’t take long for Keith Wilson to grab my attention. He was the first local politician to put what I’d seen in my daily life into plain language. Portland’s unsheltered homeless crisis hurt everyone. Other cities had succeeded where we’d failed, and our approach wasn’t working. It was time for real change, and getting folks off the streets and into shelter was a moral imperative and critical to restoring a city where people wanted to live, work, and raise families. Despite our best efforts, compassion and pragmatism don’t always successfully intersect in Portland, but here was a guy who’d traveled the nation on his own dime because he believed a solution that included both was out there, he just had to find it.

I love Portland, but there were times when it felt like the city didn’t love me back. My little hatchback car had a bullet hole from a midday shooting on Columbia Blvd. My wife was driving at the time, with my toddler son strapped in the back seat. I’d been chased through a Delta Park encampment while biking my kids to soccer practice. I’d watched a homeless man go after one of my neighbors with a pitbull and had to decide whether to try to help or get my small child to safety. Then there were the questions every bicyclist in Portland has asked themselves: will my route be blocked by tents or broken-down cars? Can I get around an RV in the bike lane without getting hit from behind? My neighborhood trail seemed okay last week, is it safe enough for my kids today?

Worse, was the feeling of helplessness. As a former Wilderness Search and Rescue volunteer, my instinct (and training) is to check on people if they look like they’re in trouble. In Portland, the smart thing to do is ride past and ignore the visible suffering in your midst. That’s a hard decision to justify to two young kids who still think their dad can do anything and help anyone.

I felt Wilson’s kickoff speech about the missteps and promise of Portland in my bones, even with my three-year-old wiggling in my arms. On my way out, I scribbled my contact information on a volunteer form as he tugged on my leg. The campaign seemed professional and well-organized, and I doubted I’d hear anything from my offer to write a few campaign fundraising emails.

Within a day or two, I got a call from Wilson’s campaign manager, Kristopher Taft. I took his invitation and took my 12-speed Schwinn out to Cyclemaster Coffee on Lombard to meet him. The campaign didn’t need fundraising emails, he told me, at least not for the moment. They needed a website, and wanted to know if I could write it, and handed me nearly two hundred pages of deeply researched policy positions.

As a writer, I’d long believed that words without substance won’t hold up to the light of day. The notes in my hand showed the opposite: Wilson had done the work, developed relationships, advanced legislation, formed committees, and laid the groundwork to successfully lead the city. I’d also soon learn that Wilson is a difficult man to turn down, a lesson I suspect many in city, county, and state leadership are now learning.

The following weeks were a blur, and I helped the growing team set up an editorial calendar, coordinate messaging, communicate on the fly, and deploy other critical skills I’d picked up over my career. The campaign continued to gain momentum. Before long, it was time to step up or step aside. I asked that Wilson appoint me his Communications Director, but with one stipulation: the moment he found someone more qualified, I wanted him to fire me. My instructions were simple: don’t worry about my feelings, just do what’s best for the campaign.

I’d remain his Communications Director through election day. Looking back, here’s what I can tell you about Mayor Wilson: he’s a great listener, he’s willing to make mistakes, and he’s always willing to change his mind. I’ve seen him on great days, and I’ve seen him on tough days. He’s the same guy no matter how the winds blow, and the Ted-Lasso-by-way-of-Mr.-Rogers persona is not an act.

I’ve also never seen anyone work harder. Portland has some tough issues to solve. The budget and unsheltered homelessness crisis would be a big deal even if we didn’t have a hostile federal administration on our heels.

Here’s the good news: Mayor Wilson’s grit, optimism, compassion, and resolve aren’t his alone. They’re our values, too. These values make a wet, hilly city one of the best places to bike in America. They’re the values that make Portland a progressive leader, and a beacon of freedom, intentional living, environmentalism, compassion, and acceptance. They’re the values that I’m convinced will take us through the coming days, no matter what those days might bring.

Taylor Zajonc is an author, a father, a bicyclist, and Mayor Wilson’s Deputy Chief of Staff.