It may sound pretentious and stuffy, but that’s also sort of the point—the event, after all, is a reminder of the station that Ryan holds in the Beltway, where he is the ultimate smooth insider, a business guy who looks like a political guy, and vice versa. His elan and connectivity presumably explain, at least in part, Jeff Bezos’s decision to put him at the helm of the Post shortly after he bought the company in 2013 from the Graham family.

At the time, Ryan was the vice chairman of Allbritton Communications and the founding chief executive of Politico, which had long since established itself as the hottest media company in the nation’s capital—thanks in no small part to its visionary co-founders John Harris and Jim VandeHei. Politico had been borne out of the complacency of the late aughts Post, which seemed content to retreat to a once-proud local paper under the leadership of Marcus Brauchli and Katharine Weymouth. Now Bezos was trying to recharge it with the spirit of its disruptor. Ryan also had a vast rolodex of contacts and connections in official Washington. In Bezos’s eyes, he must have seemed like the perfect combination of I.Q. and E.Q.: a demonstrably successful second city media executive and an emissary to the unique inner-workings of the nation's capital.

During the years of Marty Baron’s editorship, Ryan helped steer the Post toward heights that the Grahams presumably envisioned only in their past: a product-first strategy, a growing subscriber business, and, for a time, a national profile on par with their fiercest competitor, The New York Times. During the peak of the Trump years, when the organization rallied itself around the ever-so-slightly ham-fisted mantra “Democracy Dies in the Darkness,” Ryan was one of the toasts of the town.

Alas, things move quickly in the media business—particularly in the post-Trump years, and amid a recession. When Disney has lost nearly half its market cap, and David Zaslav is scrambling to service his nearly $50 billion in debt, you couldn’t blame the Post for experiencing its own post-revival blues. Indeed, during the past year and change, and notably since Ryan picked Sally Buzzbee to succeed Baron as executive editor, the Post appears to have been besieged largely by unforced errors, such as the decline of its subscription business and the absence of a post-Trump plan, various high-profile employee conflagrations, and internal animosity about remote work policies. Media companies can be forgiven their periods of malcontent, but the company’s performance looks most bleak when compared to the Times, which continues to evolve into the thinking person’s holding company of the future under C.E.O. Meredith Kopit Levien.

In the process, some Post and Politico veterans have begun to articulate their own revisionist history, arguing that Ryan coasted on the success of the Politico cofounders. Some recently relayed to me a joke that is making the rounds in Washington media circles, which suggests that Bezos accidentally hired the wrong C.E.O. He thought he was getting someone with VandeHei’s Don Draper-esque acuity and tenacity and wound up with Ryan’s Roger Sterling pedigree instead. (What’s more likely is that he may have simply misjudged how much it was VandeHei, not Ryan, who shaped Politico’s culture and business.) Regardless, many of these folks see Ryan’s deep ties to “Old Washington” mostly as a sign of a parochial worldview and limited ambition, and one that is insufficient to realize Bezos’s dreams of turning the Post into a global player that can rival the Times.

But Ryan did a lot to dispel that notion over the years as he used Bezos’s fortress balance sheet to overhaul the Post’s digital operation, grow its subscriber base and deepen its investment in its core coverage areas of politics, policy and investigative journalism. And of course, nothing helped grow the Post’s business so much as Trump. During his time in office, the Post grew subscriptions 50 percent year-over-year, surpassing the three million-subscriber threshold in 2020.

Once Trump left office, however, the Post started churning subscribers, advertising revenue declined, and the old narrative about Ryan’s limited innovation capacity returned. In the Trump years, The Times, under the leadership of C.E.O. Mark Thompson and his successor Kopit-Levien, had quietly pivoted to become a lifestyle media company moating a news business. The company aggressively broadened its portfolio of news offerings and diversified its business, acquiring Wirecutter, Serial, Audm, The Athletic and Wordle in the process and growing to more than 10 million subscribers. The Post stayed focused on its core editorial offerings, and passed on a number of potential acquisitions, including the Associated Press, The Economist and The Guardian. (Fun fact: Before Kopit-Levien joined the Times as its advertising chief, the Post tried to hire her as its chief revenue officer, sources familiar with the matter told me. Sliding doors, I guess.)

Today, questions about Ryan’s leadership have become a widespread talking point at the Post. As I reported earlier this week, a familiar complaint inside the building is that, indeed, Ryan didn’t move aggressively enough to capitalize on the paper’s success during the Trump era, and that he doesn’t have what it takes to build out a robust subscription business. And, as I reported, these frustrations go all the way to the top of the newsroom.

In private conversations with colleagues and friends, Buzzbee has criticized Ryan’s lack of strategy around editorial and digital investments, and the company’s inability to grow the subscriber business through M&A, sources who have spoken to her told me. She is said to be envious of the Times’ aggressive acquisition strategy, including its purchase of Wordle. And, most notably, she has told colleagues that she doesn’t know how long Ryan will, or should, remain as C.E.O., though she categorically denied this on the record in a brief chat with me earlier this week. “I have not told anyone that I expect Fred to leave because I don’t expect him to leave and I don’t want him to leave,” she told me.

Meanwhile, Buzzbee is also a subject of some criticism in the newsroom. Several current and former Post employees described her as lacking Baron’s leadership skills or clear vision. Baron wasn’t an effusive communicator, but he had a hard-charging commitment to investigative journalism and “the story.” These sources described Buzzbee as more of a consensus builder, perhaps the quality that made her a successful lifer at The AP, and said it could be hard to discern what she wanted or what she valued, let alone any clear sense of editorial mission. Certainly the job has been complicated by the realities of Covid, but even without looking at its P&L, media observers can recognize that the Post simply doesn’t emit the sort of newsy heat that it did only a few years ago.

In the course of this finger pointing between Ryan and Buzbee, the Post, which already lost top-tier journalists like Robert Costa and David Fahrentold earlier this year, has seen an exodus of star talent. In September, the Post’s tech and data chief Shailesh Prakash, a favorite of Bezos’, left for Google. Steven Ginsberg, a beloved top editor who was passed over for the executive editor position, left the Post this week to join the Times as editor of The Athletic—yet another potential acquisition target the Post had looked at and passed on. Meanwhile, the Post has also lost two recent sweepstakes for high-profile talents: Jonathan Martin, who left the Times for Politico, and Jonathan Swan, who left Axios for the Times. The paper courted both reporters aggressively, sources familiar with the matter said.

The unanswerable question, of course, is what Bezos thinks of the internal squabbling. Some high-level sources say Bezos has full confidence in Ryan and that the two men are in total alignment. Others believe Ryan may be more vulnerable. But what most sources say when asked about Bezos is that they suspect that he isn’t really paying attention. The widespread perception is that the globetrotting Amazon chairman and Blue Origin founder is far more focused on his myriad other businesses and his personal life to give the Post all that much thought—and that even the recent reports of internal frustrations and high-level staff departures haven’t necessarily woken him up to the problems taking place at the paper. Or perhaps he’s following another management philosophy and letting them fight it out.