Unlike Milo Yiannopoulos, who lost everything at once, retired General Michael Flynn wasn’t entirely ruined when he resigned as national security adviser on February 13.

“For your information, we are not throwing Mike Flynn off the Water Brothers surf and skate team,” Sid Abruzzi, owner of the Water Brothers surf and skate shop in Newport, Rhode Island, and a grizzled old head on the scene, told me. I called him when a line in “General Chaos,” Nicholas Schmidle’s recent New Yorker profile of Flynn, slammed into me like Chris Miller hanging up at Del Mar in 1985.

“A headstrong teen-ager, Flynn skateboarded in drained swimming pools and surfed through hurricanes and winter storms,” Schmidle writes before quoting Abruzzi.

I felt flummoxed because, to me, skateboarding still somehow feels antiauthoritarian by nature. When I was a kid, it was a way of reimagining and reclaiming the ridiculous refuse that made up the late-twentieth-century American landscape: empty pools, parking garages, curbs, cul-de-sacs.

I learned how to scrawl an anarchy sign shortly after I started skating, when I was twelve. A year or so after that, we were calling the cops who chased us “fascist pigs.” The voice of Thrasher magazine influenced my voice as an alt-weekly writer. But now alt has gone right and the guy too whack even for Trump is an ex-skater. What the hell?

I called Abruzzi because I wanted to hear what Flynn, fifty-eight, was like as a skater. I wasn’t really sure why, but I thought it might help me understand something about this regime and the world. Abruzzi was happy to talk about Flynn, whose “family lived probably a hundred yards from the shop.”

“His older brother Jack surfed all the time, his brother Charlie, his brother Joe, and Michael surfed and skated all the time,” he said. “Most of his skateboarding was done right around the period of time in the late seventies, you know what I mean, obviously riding pools and banks when available in the area—it wasn’t like California or anything—and then skating a lot of the street. And what I call street-skating back then wasn’t curbs and benches but housing complexes. They’d build the road first, the pathway, so there were places with driveways and stuff like that. So he’d be skating pretty much every day, solidly for years, him and his guys. I’m older than he was, but he had his own crew, guys his age. Most of the time they’d surf and skate when there’s no waves.”

Abruzzi said he still has film of Flynn skating. “He’s a goofy foot, classic style. Really smooth skater. He skated very smooth, very fluid style.”

“Aside from the very few mainstream moments, skating and surfing have been a very countercultural, subcultural thing. Was he part of the culture of it?” I asked.

“Completely. Absolutely. Yeah, man,” he said. “A friend of mine said he bought a guitar, played guitar. He had long hair. You know what I mean?”

“Was he a burner or anything? Was he smoking weed and stuff?”

“I can’t go there. I’m not sure what those guys did. But he was, uh, having fun. He was a regular guy, man. Good in sports, athletic. Flawless family. His sisters and brothers surfed all the time, man.”

So what happened to turn this one-time Water Brother into a potential waterboarder?

“What happened was, I’ll tell you when he sort of flew off the truck. Not flew off the truck, he’s my buddy. He had a couple things where he had to make a decision in life, I think, and he joined the, I guess, the ROTC. He changed his life around, let’s say, and decided to go in the military.”

Flynn had a distinguished career, rising to the rank of lieutenant general. But he earned a reputation for acting erratically. At the Republican National Convention last summer, he led the crowd in a chant of “lock her up,” even though army documents obtained by The Washington Post showed he had improperly shared classified documents in 2010. He retired abruptly—some say under duress—from the army in 2014, leaving a position as Defense Intelligence Agency director.

Flynn started tweeting stuff like, “Fear of Muslims is rational,” and he tried to connect Hillary Clinton with pedophilia and other crimes. He was photographed at a dinner with Vladimir Putin in 2015. He resigned as national security adviser to President Trump after it was revealed he had spoken with a Russian ambassador about the sanctions imposed by President Obama for interfering in the 2016 election and later lying about those talks to Vice President Pence.

Flynn’s successor, Lieutenant General H.R. McMaster, has called for the U.S. to work together with Muslim-majority allies. So it’s not that all military generals are Islamophobic.

“Skateboarders are lonely. Skateboarders are not well-loved,” Sean Wilsey wrote in “Using So Little,” a wondrous essay on skating.

As I was thinking about the loneliness of outcasts and the connections between Flynn the hater and Flynn the skater, I realized that one of my oldest friends and skate buddies has become a far-right Pizzagater, making all sorts of wild accusations under a fake name on Twitter.

One of his milder retweets—“Conservatism is the new counterculture”—struck me.

Maybe for him—or for Flynn—being on Trump’s side feels the same as it felt to be a skater back in the seventies or eighties. On one hand, it was a middle finger to authority, but it was also, in our cases, the rebellion of the young white man who thinks he should be free to do whatever he wants. In some ways, our Powell Peralta skeletons were the Pepe the Frog of their day.

So I shouldn’t have been surprised that Flynn was a skater and a surfer. But I’d still like to think that he might have turned out a little better if he’d spent more time surfing waves and less surfing the net.