
Just a block from the Ida B. Wells High School campus, on the corner of Vermont street and Bertha boulevard, there is an ongoing protest. A Portlander sits on his walker holding up a sign, facing a slew of honks, cheers, and obscene gestures. His sign reads “Dump Trump” on the front and “Fight Fascism” on the back.
The leader of this one-man protest is Ray Cheryl, a grandfather, retired paralegal, teacher and activist. Cheryl is in his 70’s and living with severe emphysema, a chronic lung condition. He moved to Portland about a year ago, and started protesting at this spot just a few months ago.
“Our democracy is in danger… everyone needs to do whatever they can, and that’s something I can’t do [due to his health condition],” Cheryl says. Despite his limited circumstances, he remains steady in his activism. Rather than attending major, organized protests, Cheryl chooses to spend his time leading his own act of resistance. “I feel more valuable here,” he says. “[I think] my time is better spent here than amongst 100 other signs.”
One can find Cheryl on his corner a few times a week, usually in the afternoon when traffic is the heaviest. “I hope to make people think…’we’ve got to do something,’” he says. “It takes everybody.” Cheryl protests for about two hours at a time.
Despite the small size of the protest, Cheryl still attracts attention. He reports being physically attacked two separate times due to his signs when he was protesting in Florence, Oregon. “In The Dalles, I’d get about 10 positive responses for every middle finger,” he says. Now, on the corner in Portland, he estimates one negative response for every 30 to 40 positive ones.
It’s not the honking and waves that encourage Cheryl, though. He is not there for the people who support him. “I’m here for those who are giving me the middle finger and the thumbs down. They’re the ones who need to see the sign,” says Cheryl.
Though he has only been protesting in Portland for a few months, Cheryl has been speaking out for much longer. After the results of the 2016 presidential election, Cheryl began his journey in activism. At the time, he was living with his wife in a trailer in Tucson, Arizona. “I was sure Hillary would win, had no doubt Hillary would win,” he says. “[When Hillary lost, I realized], ‘Woah, we haven’t been doing our work. We haven’t been pulling our weight.’”
The couple later moved to The Dalles, Oregon, where Cheryl began his protests. “I was known as ‘the sign guy’ there,” he says. For the past nine years, Cheryl has been working hard to make a difference. Over the years, he has made various signs. One said “Racism is Wrong,” and “Bigotry is Bad” on the other side. On another, he wrote “Hate is bad” and “Lies are Bad.”
Cheryl wasn’t always an activist. He grew up a part of the Republican party, spending his time breaking horses on a ranch in Utah. Cheryl describes his younger self as “basically just a cowboy” and someone who didn’t see the need for political change—something he attributes to ignorance.
Cheryl never graduated from high school, but after moving to California to live with his aunt and uncle, he was given the choice to stay for free if he went to college. So, he took the General Educational Development exams and majored in sociology with a minor in psychology at his local community college, before pursuing a graduate degree in education for a year.
His time at college is what changed his viewpoint. In Cheryl’s junior year, he took a constitutional law class and received pushback from his peers for his alignment with the Republican party. Cheryl recalls getting into arguments with his classmates. These debates ultimately led Cheryl to explore new ideas and perspectives he hadn’t previously considered.
This experience shaped Cheryl into the person he is today. “Education is the only cure for ignorance,” he says.
Outside of protesting, Cheryl is also a caregiver for his three-year-old grandson and six-year-old granddaughter, which takes priority.
Cheryl has never remained in one place. Between breaking horses, teaching, working in sales, oil fields and as a litigation paralegal, Cheryl has lived many lives—and continues to do everything he can.
Ray Cheryl shows that it is never too late to become an activist and every action makes a difference. “The more people who do anything, the better off we are,” he says.
Rory Seymour • Jun 10, 2025 at 10:27 am
I usually see this guy on my way to school, so its cool to know his story!