Punchbowl co-founder Jake Sherman has unending appetite for Congress

PUNCHBOWL NEWS TEXT OUT A FEW MIN AGO.

It was 8:37 a.m. on a Friday at the end of September. A pack of lost-looking journalists loitered on the first floor. A photographer stared at her phone with her mouth open. Everyone knew Feinstein was in precarious health, even as she’d vowed to finish her Senate term. The news of her death was both unsurprising and a shock. What did it mean?

“It’s a huge deal for legislating, which is like, obviously, what everyone’s focused on,” said Sherman, sitting on a bench in a spartan brick-floored terrace overlooking Statuary Hall, clad in standard-issue fratagonia: a black fleece zip-up, a blue-plaid shirt, khakis. “And especially in a tough time and a closely constructed Senate, losing a vote —”

“ — saying nothing about the death. I mean, obviously, the main focus for everybody is on the fact that she’s dead. Everybody. I mean, she’s like a legend.”

Big picture, small picture. From inside the Capitol’s scoop-industrial complex, it can sometimes be hard to tell which is which. Subtle shifts in the breeze can foreshadow monumental changes in policy, and there’s a market of professional knowers and amateur news junkies who need intel, an edge, a fix. But the rest of the world isn’t the Hill, which is why, after Sherman posted the double-barreled alert about Feinstein’s passing, critics online pounced on him for what they saw as crass self-promotion of his business — which, two-plus years on, is trying to make itself essential in a crowded field — next to the somber news. Why add that part, anyway?

“I don’t know the answer to that‚” he told me. “I didn’t think about it.”

Who has time to think about it? On the Hill, scoops and gaffes alike are subject to the same natural law: Next! There was the possibility of a government shutdown looming, presidential impeachment hearings in the mix, a Middle-East war and a(nother) fight over the House speakership over the horizon, just out of sight. And who’s going to tell you about it a few min before the rest?

Sherman, a 5-foot-6, cherub-faced 37-year-old, has made it his business to become that guy on the Hill, where the currency is micro-scoops — news about extremely incremental developments that could be stale within hours. What this has brought him is a reputation as a primary narrator of major events and minor subplots driving the news in Congress, from Republican infighting over who should get to be Speaker of the House to the question of whether a member of Congress pulled the fire alarm before a crucial vote. In addition to his outlet’s newsletter dispatches, Sherman’s play-by-play of various Hill dramas go out to more than 420,000 followers on X, formerly known as Twitter — and into the bloodstream of Official Washington. These posts often have overtones of urgency.

SCALISE IS OUT. CAN JORDAN WIN?

What can you even say at this point? The House Republican Conference is such a train wreck.

JORDAN has started making calls for speaker, after garnering 46% of the vote for speaker just a few days ago.

There are a lot of no votes right now for JORDAN: @CarlosGimenezFL​, @diazbalart​, @mariodb, @AustinScottGA08​, @RepAnnWagner, @CongMikeSimpson​ and more.

JORDAN is intent on taking the vote to the floor if he wins in the conference — not a sure thing. Some motions are already in the mix to raise threshold and sr GOP officials think those resolutions could pass

There is so much bad blood in the conference right now it’s absolutely stunning. Leadership is a mess — backstabbing right and left btwn aides, lawmakers and allies. Way worse than its ever been.

Sherman likes to signal that something is worthy of your attention by writing “NEWS” at the beginning of the tweet, adding siren emojis or capitalizing lawmakers’ names in the style of a screenplay (“RIGHT NOW — JORDAN and JOYCE are huddling on the floor”). He says he doesn’t know why or when he started doing this.

Since 2021, Sherman has co-captained Punchbowl News, a subscription-based news service he founded with Anna Palmer, John Bresnahan and Rachel Schindler; all friends who previously worked at Politico (where, full disclosure, I used to work; I overlapped with some of the future founders when I was an intern but never worked with them directly).

Punchbowl’s three daily bulletins (AM, Midday, PM) are an all-day EKG graph of Congress, chronicling the every move of influential lawmakers for a reported 100,000-plus subscribers — or “members” of the Punchbowl “community,” in the company’s argot. “Premium” community members can pay $300 a year for the privilege of getting special invitations to VIP events with lawmakers or virtual brown-bag lunches, text messages like the one that alerted Feinstein’s death and even access to surveys that track “sentiment” among senior congressional staff on issues such as whether House Republicans might impeach President Biden.

Sherman isn’t the only reporter at his company, but as an indefatigable player-coach he is arguably Punchbowl’s face. And for some members, Sherman is — like it or not — the first face they see in the morning. Punchbowl’s tipsheets have landed in the morning press clippings of boldfaced House leadership names like Rep. Nancy Pelosi (D-Calif.) and Minority Leader Hakeem Jeffries (N.Y.), while Rep. Kevin McCarthy (R-Calif.) finds his way to Punchbowl content on his own.

“I wake up really early in the morning, and I read the newsletters, and I read Punchbowl, and then it’s like, okay, depending on what’s in Punchbowl, can I go back to bed? Can I go work out? Or am I working?” said a top Democratic leadership aide who spoke on the condition of anonymity so as to avoid appearing partial to Punchbowl.

“Jake Sherman is like the sun rising in the morning,” says Aaron Fritschner, deputy chief of staff to Rep. Don Beyer (D-Va.). “This is the world that we live in, and if I want to know what’s happening, which I must do for my job, I need to read Jake Sherman. That’s just the way it is.”

“You wake up,” says Matt Sparks, former deputy chief of staff to McCarthy, “and it’d be like, ‘Well, how the hell does he know that? Oh, here we go.’ And then your phone just starts buzzing.”

Sherman’s power lies in being able to tell the story as it’s being written. And that comes from knowing things: Breaking news. Leaks. Chatter. Conversationally, people often call him “wired,” evoking his well-kept information networks.

On multiple occasions while I was reporting this article, Sherman asked me about the conversations I’d been having with other people about him — hinting that he already knew who I was talking to and, in some cases, what we’d talked about. He seemed to want me to know that, while also micro-scooping his way through each news cycle, he was also one step ahead of me on this story. In one case, he texted me that “someone at post” let him know when this article might be running. No one I spoke to on the Hill who had strong criticisms of Sherman was willing to put them on the record, and even most of those who praised him asked to speak on background first and review their quotes before agreeing to be quoted.

Sherman’s success at calling the most aesthetically dull ballgame in the country may have to do with the fact that what he always wanted to cover was sports. A self-described “failed athlete” — he played basketball as a kid, then golf on his high school team in Stamford, Conn. — Sherman covered basketball and other sports for his college paper at George Washington University, where he also served as editor in chief. He was obsessive, even back then. Former classmates don’t recall so much a temper as an intensity; one noted that he could hang up the phone in frustration, utter curse words after losing an interview and skip the stairs of the paper’s townhouse to chase someone down G Street.

He kept getting news reporting internships and not sports ones. In 2009, Politico co-founder (and former Washington Post reporter) Jim VandeHei hired him to report on House Republican leadership. Then the sports-writing dream seemed again within reach: In 2013 he caught the attention of Jason Stallman, then the sports editor at the New York Times, who wanted to recruit him to be an investigative reporter on his desk.

“He was unbelievably competitive,” Stallman told me, recalling an exchange they had at the Times’s cafeteria in New York. “He told us in the interview about how miserable he is in the morning when he sees somebody else with a story that he thinks he should have had.”

Stallman offered him the job. It was a huge deal for Sherman, who told me he keeps in his home office a reprint of the Times’ sports front page from the day he was born. But the principles of self-interest, leverage and iron-gripped handshakes apply in the world of political media, too.

SHERMAN found this out when he huddled with VANDEHEI about the job.

“So, he comes into my office,” recalls VandeHei. “And he says, ‘I’ve always been interested in sports and I’ve got my dream job — the only thing that would pull me away from Politico — and it’s to go work for the New York Times.’”

“And I said, ‘You’re not going to the New York Times. You’re under contract with Politico. You’re going to think that you can get out of that contract. You’re going to contact a lawyer. You’re going to realize the New York Times won’t hire you once they realize that we’re going to fight the terms of the contract. And you’re going to be back here doing what you’re doing right now.’”

So instead of covering sports, Sherman recommitted to covering the X’s and O’s of politics. With Palmer, he became one of the authors of Politico’s flagship newsletter, Playbook. It was 2016, and Mike Allen, the founding bard of the sleepless modern era of Washington inside-baseball journalism, had just left to start Axios — with VandeHei. “Everybody predicted, ‘Oh, Mike’s gone, that’s the end of that,’” said Robert Allbritton, the former owner of Politico. But, “it worked brilliantly, actually. Numbers went up.”

Sherman’s contract with Politico eventually did expire; and, naturally, he and Palmer left to invent the next iteration of the scoop-industrial complex. Their bet was that a market existed for a news operation focused specifically on Congress — its players, their strategies and the jostling for power. (As Playbook authors, the pair had written a book whose title now seems even more fitting, in light of this venture: “The Hill to Die On.”)

I asked him how his job was different these days from writing Playbook. Sherman, the competitor, had this to say of his Politico bosses: “When we quit, their criticism of us was just, ‘They’re too focused on Capitol Hill. We don’t want Playbook to be Capitol Hill.’” He paused, smiled, raised his eyebrows and drummed his fingers. “That seems to have changed in recent days, weeks and months for them, right?”

Earlier that week, Politico announced it was rebooting its Capitol Hill coverage with a new live-updates feed named “Inside Congress Live,” and shifting one of its newsletters to publish in the evening, around the same time as Punchbowl PM.

Politico editor John Harris bristled at the suggestion that these changes were influenced by Punchbowl’s success. “I think a lot of it is influenced by me,” he told me at the publication’s Rosslyn, Va., headquarters, leaning back in a black leather armchair and pointing at himself.

Anyway, Politico had had “among the best of months” in its Hill coverage, he said — audience doubling, page views tripling, et cetera, et cetera. “Whatever the size of Punchbowl is, is up against a team of literally dozens,” Harris said, praising his own reporters for bringing “more depth, more breadth, more style, more authority.” Punchbowl, he said, was still at the early stages of distinguishing itself in a field crowded with other next-gen iterations of the Politico start-up model. “What Jake and Anna did is not exotic. What I will say is, it’s damn hard.”

(About an hour later, Sherman texted me: “How was Harris.”)

For all its emphasis on subscribers, Punchbowl has succeeded in part by cultivating relationships with the business giants who want to influence the Washington-insider types who wake up with Sherman and company. Selling advertising to corporate brands — like Duke Energy, Walmart, Boeing and Meta — is a big part of their business: According to Axios, Punchbowl is on track to make $20 million in revenue this year, with the majority of that revenue coming from ads and event sponsorships.

“If you look at media start-ups that have been successful over the last 15 years, there actually aren’t that many of them, and they’re disproportionately in Washington. Politico, Axios and then Punchbowl — a lot of them come from the same DNA,” said Ben Smith, the former Times media columnist who once worked for — guess — Politico and is now a co-founder of the year-old news website Semafor.

“If you’re reaching an audience that advertisers want to reach,” Smith said, then there’s money there.

There was a rumor going around that Sherman had made enough money as a journalist-impresario that he was thinking of becoming a part-owner of Kelly’s Irish Times, a pub near Capitol Hill. “He and I were joking,” Allbritton said when I asked him about it. He remembered Sherman saying something like, “Hey, we should go buy a bar together,” and that he’d replied, “Yeah, sure! You’re rich! You can afford it now.”

Sherman recalls joking around with Allbritton, but said the bar idea wasn’t a serious suggestion. “I don’t have the money and I certainly don’t have the time to run a restaurant right now‚” he told me. Then he added: “But wouldn’t it be cool if there’s, like, some place on the Hill where people could go to congregate?”

As in, a place on the Hill where everybody could go after working on the Hill all day.

“If you are one of the many Americans who hates Congress, this book is for you,” read The Post’s review of “The Hill to Die On,” but Sherman himself doesn’t feel that way. “I love Congress,” he told me in September, sitting at a booth in a dingy cafeteria in the Capitol basement. “I love it. I think it’s the most interesting story in the world.”

He planted his index and thumb on the tabletop and was making broad circles on it, his eyes fervid.

“This is always going to be the center of our universe,” he said. “Always.”

In September, the most interesting story in Congress was about whether McCarthy would be able to successfully negotiate with the White House and his party’s right flank to avoid a government shutdown. McCarthy emerged from a closed-door GOP conference meeting (whose contents Sherman had been tweeting from the outside) and prepared to address the journalists who had assembled in a blue-carpeted hallway a flight of stairs below the Capitol Crypt. Sherman was eager to ask questions, but an aide told him to wait until he got to the microphone.

En route, McCarthy murmured to Sherman: “You’ll get first question. Since you have an ironed shirt on.”

Sherman started laughing: “Ironed shirt?”

“His shirt is not as wrinkled today, so he gets the first question,” McCarthy told the other reporters.

Sherman also got the second question. Later, the Republican leader interrupted a different reporter to permit Sherman to ask another follow-up. And when the formal Q&A was done, McCarthy took some more questions from Sherman as other reporters pursued him through the halls.

Maybe his edge comes from hustle. But there’s a perception among some on the Hill that Sherman cultivated a particularly friendly relationship with McCarthy that allowed him to glimpse into the then-speaker’s thinking and publish it in Punchbowl’s newsletters.

The two men have known each other a long time, and Sherman seems as tuned-in to the wrinkles of McCarthy’s point of view as McCarthy is to the wrinkles of Sherman’s work attire. After the California congressman won the speaker’s gavel, Semafor reported that Sherman had a close friendship with Dan Conston, the head of a McCarthy-aligned super PAC. Sherman had gotten to know Conston in college, and the McCarthy ally had later served as the narrator of a tour of D.C. landmarks for guests at Sherman’s 2015 wedding. Conston told me he has worked with Sherman in the course of his job — like he works with other Punchbowl reporters — but he downplayed any notion that he helped his friend get sourced-up with McCarthy’s circle. “He doesn’t need my help,” Conston said. “He knows all the members, all the key staff.”

In May, amid the debt ceiling crisis, some liberal commentators grumbled that Punchbowl was writing too uncritically about McCarthy’s perspective. David Dayen, the executive editor of the American Prospect, argued then in an essay that there’d been “almost no daylight between McCarthy’s debt ceiling demands and what Punchbowl has reported as the essential elements for a deal.” And then there are almost telepathic insights like this item from January, about how McCarthy would explain to fellow Republicans the deal he’d reached with the party’s right flank to get their support: “McCarthy planned to use a conference call instead of an in-person meeting because such calls are easier to manage. In-person meetings tend to be unruly and unproductive.”

“It’s the kind of information you can only faithfully, confidently report if you’ve had a conversation with that person or someone very, very, very close to that person,” Mike Casca, the deputy chief of staff to Sen. Bernie Sanders (I-Vt.), said of Punchbowl’s reporting.

“How else are they getting those inside-the-room quotes and stuff?” Casca said. “But that’s the thing: That s—’s been happening since the beginning of the relationship between politicians and reporters.”

Sherman took exception to any suggestion that he and McCarthy’s team were too close. “What the speaker says is newsworthy,” he told me the morning of the Feinstein news. “We are critical — analytically critical, and critical in the sense that when he falls flat, like he did last week, when he failed to pass two rules, like, that was bad.” (Sherman also noted that Punchbowl’s subscriptions “exploded” during the debt ceiling fight.) As for his friendship with Conston, Sherman said: “I wasn’t going to change my career because he is my friend, nor was I going to not be his friend anymore because of his own career ambitions. We’re all adults.”

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Big picture, this is how adults operate on the Hill, according to Sherman: “Sources give you information not because they like you, not because you’re friends with them — they have an incentive to give you information,” Sherman said. “At the end of the day, they need us way more than we need them, for this reason: because there’s a lot of them, and there’s few of us.”

By the middle of October, MCCARTHY’s speakership was dead, but SHERMAN’s X feed was as lively as ever. SCALISE’s bid for the gavel was ancient history. JORDAN had been meeting one-on-one with his skeptics, landing “massive” endorsements from Republicans ROGERS, CALVERT and WAGNER, as well as FERGUSON, ADERHOLT and WITTMAN. ESCOBAR, like other Democrats, was trying to argue that “the only path forward is a bipartisan governing coalition,” but Punchbowl’s play-by-play man wasn’t seeing it. Ahead of a closed-door Republican meeting on Oct. 16, SHERMAN described his view from the center of the universe.

The most likely path forward at this point, based on all available evidence, is that Jordan is very close to becoming the 56th speaker of the House.

PANERA BREAD is the food of choice tonight for the House Republican Conference.

Nineteen minutes later, an update:

I am now told carmines is the food tonight. Maybe there’s also some Panera. But carmines is here.