Observations from Portland’s East Side

I recently met up with an old friend for coffee on the East Side of Portland. To be honest, I don’t venture over there much. It’s known for its progressive atmosphere, heavily leaning into “social justice” themes.

You can spot an abundance of “WE BELIEVE IN SCIENCE” signs and pride flags. There’s no shortage of left-leaning symbols displayed openly.

I mean, who would dare to wear a genuine MAGA hat over there? You could find yourself in a confrontation, especially with someone sporting a face tattoo.

The East Side isn’t without its dangers, either. Stabbings, shootings, and cars crashing into homes aren’t uncommon.

I reside on the West Side, where people tend to be more reserved, perhaps even reasonable. Still, there’s a good amount of science and pride seen there as well.

Unexpected Encounters

So, I parked at a local café for our meeting. The sun was shining, and the outdoor seating was lively. There was a lesbian couple at one table, a few slim tattooed guys at another, and a woman in a quirky dress, oddly sporting a tuft of gray hair beneath her chin. That caught me off guard.

As I reached for the café door, I noticed myself in the glass reflection. I was wearing a bright red Phillies baseball cap.

If you’re not familiar, the Phillies are a baseball team from Philadelphia, decked out in red and blue. Yes, their hats are red.

I also have a navy blue Boston Red Sox hat, a brown San Diego Padres hat, among others. I tend to wear them all at random. I play softball in the summer, which is why I like to switch it up.

But here’s the catch: the Phillies cap’s red is quite close to that of a MAGA hat. So, folks might mistake it for something more controversial at a glance.

Thus, the Phillies hat hasn’t seen much action lately. I wore it occasionally while Biden was president, but now that Trump is a player again and Portland is, let’s say, in a state of “Trump derangement,” I’ve kept it away.

Braving the East Side

Earlier that day, I donned the Phillies hat while running errands on the West Side, where no one cares about hat colors.

But on the East Side? Oh, they care—a lot. I walked past a woman with a gray beard who seemed to be sizing me up, perhaps checking my hat. Since it didn’t scream “Make America Great Again,” she lost interest and returned to her coffee.

Who, seriously, wears a real MAGA hat there? No one, really. I tend to hang out in trendy coffee spots. You’d be tempting fate.

Staring at my bright red hat in the café door’s reflection, I faced a choice: wear the Phillies cap and risk attention—or head back to the car and stash it away?

It does feel a bit ridiculous to let a hat dictate my mood. Can’t I just wear what I want? Isn’t that the essence of freedom in America?

Reflecting on MAGA Merchandise

I used to have MAGA hats back when I volunteered for a Republican gubernatorial candidate in 2018. At one point, someone handed them out. But let me tell you, the quality was abysmal. The crown was poorly stitched, sticking up like a clown’s hat.

Then I found a pristine white MAGA hat. It looked fantastic, yet I’ve never actually worn it. It’s safely stored away, almost like a treasure.

Decision Time

Standing at the café, I scrutinized my reflection again. A large white “P” emblazoned on the front clearly identified it as a Philadelphia Phillies hat—common sense right there.

But the left can be unpredictable. In a place like Portland, it’s often safer to tread lightly.

Plus, my old friend who was meeting me likely leans left as well. While we didn’t talk about politics, living on the East Side means he’s probably adjusted his views—even if they differ from his true beliefs.

Did I really want him to awkwardly wonder, “What’s with the red hat?” when he spotted it?

No, I didn’t. I certainly didn’t want unwanted attention or to deal with a barista who might take out their frustrations on my drink.

Hat Swap

So, I went back to my car and tossed the Phillies cap into the trunk. Thankfully, I discovered an old, crumpled Dodgers hat and quickly put it on.

That seemed to solve the problem—though I did catch a suspicious glance from that white-haired woman.