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David Bailey is irreverent, and that makes the 50-year educator fit to be the face of a Portland parade.

COURTESY - David Bailey enjoyed 50 years of teaching at Lincoln High School. Now retired, Bailey was tapped to be the grand marshal of this years Starlight Parade. Fifty years ago, David Bailey looked barely old enough to be teaching the students in his classes. He began his first year of employment at Lincoln High School in 1968, at just 22 years old. The Vietnam War was raging, social unrest was ever-present, and even back then, the building he taught in was considered old. 

Bailey, now 74, spent five decades teaching at Lincoln High before retiring in late 2018 — a tenure and status that led the Rose Festival to naming him as grand marshal for the June 1 Starlight Parade. 

It's hard to tell whether the lifelong Portlander stuck with it because of dedication, stubbornness, or both. 

On a sunny afternoon in a Southeast Portland café, Bailey eyes up a pastry case, settling on a pecan crumb cake. The server grimaces when he asks if the confection can be heated up. 

She concedes, offering to microwave the pastry for a few seconds. 

"Perfect," Bailey beams. "I cook all my meals in the microwave." 

He's not kidding.  

By default, Bailey is old Portland, whatever that means. He held the same job at the same school for 50 years and he's lived in the same Southeast Portland apartment since the 1970s. He went to Portland public schools before attending Portland State University and devoting his career to teaching high school in the city he grew up in.

"We're still a small town, aren't we? I think in a lot of ways, we're a big, small city," he says, reflecting on the evolution of Portland. "But, I go into the Pearl District sometimes and I don't recognize it."

He doesn't like change for the sake of change and he doesn't like a lot of things about modern culture — mainly the lack of diversity in political and social dialogue, but he did love at least one thing, and he stuck with it for longer than most. 

"That's what I love about teaching," Bailey says between bites of crumb cake. "It's an intellectual sport. It's intellectual jousting. I think I was part of something wonderful."

As a social studies and history teacher, he took pride in challenging his students to flex their mental muscle and consider perspectives other than their own. He considers himself the vehicle for critical thinking, but tried hard not to be the destination.

"I will always let you know where I stand on something, but I don't want any of you to feel you have to buy into it," he'd tell his students. "I just want you to think. What you think is not my business." 

Some Lincoln students recount Bailey wearing a Make America Great Again shirt during his last year of teaching. They weren't sure if he was showing his political leanings or inviting debate for debate's sake.

Bailey's been around long enough to have taught two, sometimes three generations of family members. He can recall a young Ted Wheeler and Jules Bailey strolling the halls of Lincoln High.

He never had kids of his own.

"I had 12,000 of them over the years and that was enough," he jokes.

Bailey retired right before a wave of educator protests hit the state in early 2019, the latest causing school districts throughout Oregon to shut down on May 8 as thousands of teachers walked out or didn't show up for school, to rally for more education funding at the state level.

It seems notable that this year, Bailey, who spent nearly his entire adult life teaching, was named the grand marshal of the Starlight Parade.

"It's cool," he says of being asked. "I can think of a whole lot of more deserving people, but by God, if they're asking me, I'm gonna do it."

He contends he should've been "the person who follows the horses with the scooper," but admits, "I like the idea of putting focus on public educators."

But Bailey is no poster child for the fired up, fed up teachers marching through the streets in red. He's more prone to sit back and put everything into context.

"I firmly believe the public has an obligation to provide proper funding to public schools. The challenge is what you do with those funds," Bailey says. "I always respect my colleagues. But, I would challenge the thinking, the mindset of the protests. Did that shake people at the state Legislature? I don't think so." 

PMG PHOTO: COURTNEY VAUGHN - David Bailey chats at a cafe in southeast Portland. Bailey is the 2019 Starlight Parade grand marshal.Amy Johnson, Starlight Parade chair, said Bailey embodied what she and her committee look for when choosing a grand marshal.

"Most of us can say there's that one teacher," Johnson notes. "It all started because the conversation around Starlight is really such a Portland parade. It's really highlighted the uniqueness of our city. It doesn't really seem like the outward celebrities really fit in that parade. It's always someone who brings us back to Portland."

As Bailey collects the last of the crumbs from his plate, he offers more perspective, as if he never left the classroom. "You're gonna be measured by what you do for other people," he says. "You'll also be measured by what you do to others."

Bailey's appearance at this year's Starlight Parade is a mark of what he's done for others, but he's careful not to take the event, or himself, too seriously.

"The Starlight is properly irreverent," he suggests. "I don't have a problem being properly irreverent." 

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