Rob Olson, 42, manager of a company called Action Images, was wearing a hat that looked similar to a Washington Redskins cap, but this one had the cap emblem removed, to make it look like he was wearing a W skateboard. The Washington Pride Day 2016 event in September 2015, he said, was the inspiration for the cap, which is handmade, with an authenticity that might have allowed him to skate past Washington city security.
As he stood near the skating rink, Mr. Olson was not using it for any unusual maneuver. “I use it to follow around the new mayor, Muriel Bowser,” he said, referring to the incoming city manager.
Those who attend pride events say they tend to enjoy roller skates, skateboards and occasionally, bikes. Mr. Olson had bought the derby wheels online, fitted with a conventional skateboard. The skates — in black, with colorful themes — also come with helmets and workout belts. “I do a little cardio walking,” Mr. Olson said.
Mr. Olson had a couple of back-and-forth photos with the Trump 2016 campaign team, where the candidate thanked Mr. Olson for his work in tapping their database. He got a title from the campaign, which said Mr. Olson “represented the New Media Shop.”
“And I just really had a great time when they thanked me,” Mr. Olson said.