WASHINGTON — During the Clinton presidency, The New Republic billed itself as the in-flight magazine of Air Force One. Former President Obama loved The Atlantic. President Trump prefers Barstool Sports, the sophomoric, in-your-face sports blog beloved by bros of all stripes.

The president — who noted this week that “Nobody likes me” — is always looking for a friendly ear in the media. But unlike Fox News, the frat-boy blog turned media empire is known more for its dude content — “Man Vs. Wasp Nest – Who Ya Got?” reads one recent headline — and “Local Smokeshow of the Day” gallery of babe photos than for its political coverage.

Barstool’s founder, Dave Portnoy, 43, began his first White House sit-down last week with an appeal. “Your son’s a big fan of our website. Even before this started, I was trying to get a retweet out of him for about six months,” he said. He also complained to a sympathetic Mr. Trump that Anthony Fauci, the nation’s top infectious disease specialist currently grappling with a raging deadly pandemic, “is on my ‘X’ list, because every time he talks and says the country should stay inside, my stocks tank.” The interview ended with Mr. Portnoy dialing up his father for a surprise FaceTime call with the president.

And so groaned the Walter Cronkite-wannabes in Washington, of whom there are many.

When Mr. Portnoy arrived at the White House complex, young staffers clamored to take selfies with him. Eric Trump tweeted out a promo photo of his father being interviewed, writing: “Two legends!”

Though Mr. Portnoy stated in his interview that he is “apolitical,” he was ahead of the curve on the Trump movement when, in 2015, he announced he would vote for the reality TV star. “I don’t care if he’s a joke,’’ he wrote. “I don’t care if he’s racist. I don’t care if he’s sexist. I don’t care about any of it. I hope he stays in the race and I hope he wins. Why? Because I love the fact that he is making other politicians squirm.”

Mr. Trump, in turn, had become familiar with Mr. Portnoy’s signature pizza reviews and his appearances on Tucker Carlson, where Mr. Portnoy has expressed uncertainty about Dr. Fauci and decried the overreach of political correctness.

Together, both men have a history of ugly remarks on sexual assault and race, and are, to the delight of their respective fanboys, unlikely to ever apologize. One of those mutual fans is Elon Musk, the Tesla magnate and increasingly Trump-aligned brozilla, who tweeted at Mr. Portnoy in May: “Please run for office. The politicians & unelected bureaucrats who stole our liberty should be tarred, feathered & thrown out of town!”

In March, one of Mr. Portnoy’s colleagues interviewed the Vice President’s chief of staff, Marc Short. More recently, White House press aides had been kicking around the idea of a Barstool interview with Mr. Trump — a chat on Air Force One was one thought — and ultimately settled on last Thursday, the opening day of baseball season, before reaching out to Barstool. (Through a representative, Mr. Portnoy declined to be interviewed for this story.)

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.”

For Trump aides, the perils of overexposure are well-known. Mr. Miller and other senior officials have been scorned or yelled at in restaurants. Some younger aides choose to go incognito altogether, inventing alternate identities if they meet someone while out — like one press wrangler who pretends to be a real estate agent. Others spout the ultimate D.C. safe words: “I work in fund-raising.”

Spend a Saturday night with young Trump staffers and one hears basic things like “Alexa, play Top 40!” Vodka shots are administered in plastic TRUMP PENCE 2016 campaign cups. Nostalgia rules for the days of the first scrappy campaign, when victory seemed impossible and everyone doubted them.

A major Trump White House watering hole is Mission Navy Yard, a bar near the baseball stadium where the Nationals play. One low-level National Security Council staffer even moonlit as a bartender there. Another spot is “The Lot,” across the Potomac, in Arlington, where aides congregate with buckets of White Claw, the boozy seltzer drink.

With Ivanka and Melania as the models for women, the understated Tory Burch flats and tight ponytails are out; in are the knee-high boots, party dresses and big blowouts. The Trump White House has a Palm Beach look. Aides keep stilettos in desk drawers, should they be called into the Oval.

The men may have it worse. The Washington Post reported that, earlier in the first term, Trump bros vaped and engaged in “Icing,” in which Smirnoff Ice bottles are hidden and must be chugged when discovered, a game familiar to anyone who spent the early 2000s in a dorm.

A 2011 YouTube video of Johnny McEntee, then at University of Connecticut and now a high-ranking Trump official, landing amazing football trickshots is the stuff of bro legend in this West Wing.

But there is an upside to this Barstool-Trump match made in bro-town. Real Trumpologists will note that Mr. Portnoy’s friendly interview yielded something ultrarare from this president: a moment of contrition.

In the interview, Mr. Trump allowed that he does often regret his time on Twitter (a platform on which he has recently suggested, incorrectly, that he can delay November’s election). “It used to be in the old days before this, you’d write a letter and you’d say, ‘This letter is really bad.’ You put it on your desk and you go back tomorrow and you say, ‘Oh, I’m glad I didn’t send it,’” the president said. “But we don’t do that with Twitter. We put it out instantaneously, we feel great, and then you start getting phone calls, ‘Did you really say this?’ I say, ‘What’s wrong with that?’ And you find a lot of things.

“You know what I find?” said Mr. Trump. “It’s not the tweets. It’s the retweets that get you in trouble.”