As millennials continue to cord-cut ESPN into irrelevance, Trump aides have correctly identified Barstool Sports and its network of popular podcasts and social media personalities as a way to reach younger voters, a demographic with which this president is underwater. It is both a cultural fit and an untapped resource: A Morning Consult poll this week stated that “Barstool sports fans are younger, more Republican and more politically engaged than the public overall.”

“He’s smart to reach out in that regard, it humanizes you,” said Sig Rogich, a former media adviser to President George H.W. Bush. In his time, Mr. Rogich facilitated successful collaborations between Bush I and the National Collegiate Athletic Association and Sports Illustrated. “If Trump can create connectivity with the sporting world, it’s a plus for him. There’s no downside to it,” Mr. Rogich said.

Besides, maybe Washington is just the place for a guy like Mr. Portnoy after all.

There are so many pink-hued Vineyard Vines shorts here in summer that 14th Street often resembles an Alaska salmon run in May. As Jim Webb, the Democrat and former senator, once said about the town’s defining work of architecture: “Watching the white phallus that is the Washington Monument piercing the air like a bayonet, you feel uplifted.” (Speak for yourself, dude!)

There is something about working in the White House, in particular, that inspires Greek life-like behavior. Nicholas Syrett, the author of “The Company He Keeps: A History of White College Fraternities,” said the similarities stem from “the degree to which it is both insular and all-consuming in terms of socializing and work, and the degree to which they would see themselves against either the world or against their critics.”

With every administration, White House staffers cling to a culture of conformity.

The idealistic, progressive bros who rode into town on the waves of Obama’s historic victory were treated as young princes of the city, but they became wary of a press corps that wanted every little piece of them. Their modus operandi was to throw house parties, where they could do keg stands in peace. When Jon Favreau, then a young Obama speechwriter, and his buddy Tommy Vietor, then a press aide, played a game of shirtless beer pong at a Georgetown bar, they got burned when photos circulated. Politico huffed that the administration’s critics saw the aides as behaving like two “frat boys in the midst of two wars and the Gulf oil spill.”

Mr. Vietor said the culture of the Obama White House doesn’t even compare to what came after it. “I’d argue that the big cultural problem with this White House is hiring white nationalists like Stephen Miller,” he said. “Put down the tiki torch and pick up a baseball.”