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Jun 29, 2026, 06:28AM

The Skateboarder and the World’s Coolest Security Guard

He saw nothing.

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The scene: a six-floor parking garage in Maryland that’s operated by a university.

The atmosphere: a perfect low-humidity, blue sky summer day.

The protagonists: a skateboarder and a security guard.

There are two protagonists. That’s because I just encountered one of the coolest security guards I’ve ever met. For skateboarders, security guards are usually the enemy. Not this time.

I was riding at a parking garage that’s in a suburban area and owned and operated by the University of Maryland. With classes out for the summer, I had the place to myself. I usually like to ride on the open suburban streets, but today I felt like getting into a Zen groove—and didn’t feel like walking up hills. In an empty parking garage you ride down then take the elevator back up. It’s like repeating a mantra.

I’d been there for about an hour, and had just taken the elevator back up. I took my helmet off to enjoy the breeze for a few minutes, stopping to gaze off at Sugarloaf Mountain in the distance.

That’s when the security guard showed up. He emerged out of the elevator bay, a handsome black man who looked like he was in his 30s. I pointed to my Carver board and helmet. “I’m just riding,” I said.

His body language was easygoing. He said something about how I’m not supposed to ride here. I nodded. Then I said, “One more time?” I pointed down into the cavern of the airy garage, indicating I wanted to go one more time before heading home. I didn’t mind. I’d set up a photo shoot with a model who’s helping me promote the Anti-Communist Film Festival, and was expecting to get a text from her confirming the time and location. It was time to jet.

The guard said, “Okay.”

I pushed off. That’s when something funny happened. I rode down and when I descended onto the fifth floor, the guard emerged from the side stairwell. He’d matched my trajectory by hustling the stairs. He came out the exit and walked about 10 feet. He then turned his back to me and looked out of the big rectangular opening between floors and onto the campus.

What was he doing? I zoomed along, my wheels humming on the concrete underneath.

Fourth floor. And here he was again—off to the side at the stairwell entrance. Again he marched a few feet, tuned his back to me and looked out at the trees.

That’s when I figured it out. He was supposed to escort me out of the garage, but didn’t want to be a killjoy. So he let me ride, making sure I found my way out while he simultaneously avoided seeing me ride. He was doing his job yet could claim that he saw nothing. Skateboarder? What skateboarder?

I started to laugh as I dropped to the third floor. His stoic, intentionally avoidance had become comedic. And there he is! Popping out the stairwell door, walking a few feet, coming close enough to hear my wheels and even feel the breeze as I blew past, yet—arguably and to his superiors—oblivious to my presence.

This was the coolest security guard of all time.

Second floor. We knew the drill now. Just then a text pinged on my phone. I did a cutback and drew my phone out of my pocket. It was the Anti-Communist model. “Ready to shoot,” it read. “Wardrobe is jean shorts and an American flag bikini top.”

I slipped the phone in my pocket and blew past the guard.

First floor. At this point it might be nice to say that the guard and I exchanged a parting word or gesture, a behind-the-back fist bump or code word. That would’ve been inappropriate. The security guard had done something honorable, and skateboarding is an iconoclastic art form that’s nonetheless steeped in honor. Honor indicated we say nothing. We didn’t need to.

I cruised out of the exit and into the world.

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