It sounded like a riddle, the question the new boss posed to Washington Post Executive Editor Martin Baron in a 2013 meeting.

“Why are you taking the pain,” Amazon founder Jeff Bezos asked Baron and a small group of executives shortly after he purchased the company, “and not taking the gift?”

Baron knew all too well what the “pain” was. He had come to The Post earlier that same year, hired in large part for his reputation as a newsroom leader who knew how to do more with less. At the Miami Herald, he oversaw coverage of the disputed 2000 presidential election and the Elián González immigration drama, before moving to the Boston Globe and guiding its Pulitzer-winning investigation of the Catholic Church’s sex abuse scandal — during years when both newsrooms endured financial constraints or deep cuts.

It was understood that a similar balancing act would be expected of him at The Post, where he had just overseen a blockbuster series of reports about surveillance overreach by the National Security Agency — even as he privately anticipated the likelihood of having to preside over major budget cuts after The Post’s years of financial decline.

So that was the pain of which Bezos spoke. But “we sat there wondering what the gift was,” Baron recalled, “because none of us were quite aware of it.”

The gift, Bezos explained, was the Internet — which had given The Post the power to distribute its work worldwide for negligible cost. So, how was the company going to take advantage of it?

The meeting marked a turning point for The Post — and for Baron, who is retiring Sunday after eight years at the helm of the news organization.

It was a partnership forged at a crucial time, allowing the print newsman to help reinvent the company’s business strategy for the digital age. And The Post’s revival in turn empowered Baron — a normally reserved personality — to take up the mantle as a leading advocate for press freedoms when the industry came under attack during the Trump administration.

“I’ve long felt that we don’t speak up for ourselves well enough, often enough, forcefully enough, and that somebody has to do it,” Baron said. “I’m not one who naturally was looking for a limelight, but who was going to do it? Who was going to speak up for us? I felt that nobody was doing that.”

The biggest challenge Baron saw when he started at The Post in the first week of 2013: "We didn't have a clear vision about how we were going to get out of the mess that we were in."

At a time of aging readership, steep print circulation declines and the loss of ad revenue to digital players including Facebook and Google, The Post had avoided the major layoffs imposed by many other regional newspapers. But its ranks and its ambitions had been thinned by staff buyouts and positions left unfilled.

The effect was plainly visible to Baron, in a news product he found at the time to be lacking in investigative and accountability reporting.

“And I was surprised by that,” he said, “that here we were with The Washington Post, and some days we were struggling to figure out what would be worth putting on the front page.”

Meanwhile, it seemed to him that the staff was unnecessarily demoralized by the fact that its longtime rival, the New York Times, appeared to be thriving. Baron, though, saw opportunity. “They can be the U.S. Army, and we can be the Special Forces,” he said. “And you know, the Special Forces can win the war.”

It was a pragmatic optimism that Baron had also shown in his earlier roles overseeing newsrooms whose flush days were past. At the Herald, “he came in and said, ‘This is the hand we are dealt,’ ” said Alberto Ibargüen, who was publisher when he hired Baron as editor.

He displayed a sure-footedness in managing staff and stories. “He demanded more from the people we had,” Ibargüen said. “His insight was we didn’t need to go around hiring reporters from every which place; he just needed people to step up and do the reporting they are capable of.”

Retiring Washington Post executive editor Marty Baron says there will always be a need for journalism and accurate information in a democracy. (The Washington Post)

The publisher also observed Baron’s deft salvage instincts at work with the printed word. In one news meeting, he said, Baron quickly assessed a struggling story: “He said, ‘Your lead is here,’ pointing to the tenth paragraph, ‘and you need to answer these two questions’ — and then the story ended up on the front [page].”

Despite having come up in the era of print, Baron says he was pushing for digital innovations long before he teamed up with Bezos. In Boston, where he spent more than 11 years, he integrated the newsroom of Boston.com into the Globe, encouraged the development of online video, and formed what he described as a tiny online-audience team.

His specialty, though, remained his talent for overseeing a team as it conceptualized and launched ambitious investigative projects — notably the Boston investigation that exposed the Catholic Church’s coverup of priests who had abused children. The saga was turned into the 2015 film “Spotlight,” which won the Oscar for Best Picture.

On June 2, 2013, five months after Baron started at The Post, he joined former Los Angeles Times executive editor John Carroll for dinner at the home of Alan Miller, president of the nonprofit News Literacy Project. Toward the end of the evening, Carroll turned to Baron and asked, “So, have you found your Catholic Church yet?”

Baron appeared startled but quickly regained his poker face, Miller recalled. “We’ll see,” he responded. (“Did you see the look on Marty’s face?” Carroll said to Miller the next day. “He’s got something.”)

Five days later, The Post reported that the NSA had been conducting widespread, secret surveillance of the Internet, sweeping up the data of U.S. citizens. The prizewinning series of stories prompted congressional inquiries, spurred information technology companies to enhance encryption of their Web traffic and started a national conversation about the balance between national security and privacy.

A similar epic of government accountability reporting during Baron’s tenure was The Post’s Afghanistan Papers series in late 2019 — secret government documents revealing that high-ranking U.S. officials had long been aware of the unwinnable nature of the Afghanistan war and the corruption plaguing U.S. aid distribution but never revealed it to the public.

It was over drinks at the Madison hotel bar, near The Post's then-headquarters, that publisher Katharine Weymouth delivered the bombshell news to Baron in August 2013, seven months after she hired him:

After 80 years of ownership, her family had agreed to sell the company to Bezos.

Baron said he welcomed the news — even as he half-expected that Bezos, who “is certainly entitled to,” would want to replace him.

“I had long felt — actually well before that — that we needed fresh thinking in the industry,” he said. “Because I was not hearing any new ideas from anybody.”

For decades under the Graham family, The Post had defined itself as an essentially regional newspaper that happened to be in a very consequential city. That was the identity that steered its strategy for news coverage, circulation and ad sales. Similarly, Baron recalled, “we were shrinking with that in mind, and cutting costs with that in mind.”

Then Bezos arrived. Wrong strategy, he said.

In that first meeting, he encouraged Post executives to embrace the brand it established during the Watergate era as investigators and truth tellers and use it to build a national and international audience.

In a second meeting, at Bezos’s Seattle-area home, the tech magnate continued to press Post executives for ideas that would appeal to a national audience, as well as ones that would attract younger readers. When Baron and his colleagues returned with a more refined set of ideas for new products — blogs and reporting teams focused on opinion, policy and political analysis, and overnight news from around the country among other areas, as well as new visual presentations for Post stories — Bezos agreed to fund them.

“That,” says Baron, “was the beginning of providing us a bridge to the future” — an investment in desperately needed new initiatives without taking from areas in ways that would alienate traditional subscribers.

Other than crafting a new motto for The Post — “Democracy Dies in Darkness” — Bezos otherwise left editorial decisions up to Baron and other Post executives.

During Baron’s tenure, The Post grew to have more than 3 million digital-only subscribers, even as print circulation has declined, and has enjoyed five straight years of profitability. The staff grew from 580 to more than 1,000. The Post opened new bureaus, after years of shuttering them, and this year expects to have 26 locations around the world. The Post, under Baron’s leadership, has won four Pulitzers for national reporting, two for explanatory reporting and one each for public service, investigative reporting, criticism and photography.

“Had The Washington Post kept only a local focus it would have failed, however great its digital tools,” said Emily Bell, director of the Tow Center for Digital Journalism at Columbia University. Baron, she said, “operated as an editor who was wedded to news but not to paper. He was happy to see engineers in the newsroom, anxious to get reach and impact for stories and clear-eyed about the trade-offs.”

Bezos’s money alone would not have been enough to save the paper, she added. “If we have learned one thing in the past 20 years it is that digital newsrooms succeed on the strength of their journalism primarily. . . . We’ve seen plenty of very innovative newsrooms fail.”

See the celebration in The Washington Post newsroom as they were awarded two Pulitzer Prizes for their reporting in April 2018. (Erin Patrick O'Connor, Nicki DeMarco/The Washington Post)

Less than two years after Bezos purchased The Post, Donald Trump descended the escalator at Trump Tower to announce his candidacy for president.

If Bezos provided a bridge to the future, Trump threatened to blow it up.

During his campaign, Trump ran against the mainstream news media almost as much as he campaigned against his opponent, Hillary Clinton, and repeatedly denigrated individual reporters covering him. In June 2016, as he closed in on the Republican nomination, he blocked Post reporters from attending his campaign rallies. The campaign eventually relented, but Baron never contacted Trump directly to appeal the revocation of credentials for Post journalists.

“I think that’s what he was looking for, so that he could say we were begging,” said Baron. “If he didn’t want to give us credentials then we’d find another way to cover him.”

The Post found those avenues, notably with David Fahrenthold’s 2016 reporting in which he documented Trump’s charitable giving by calling 450 organizations to ask them whether Trump had donated money and using Twitter to crowdsource the public’s collective knowledge of Trump’s giving.

Trump’s constant attacks enlivened in Baron a sense that there was a serious new challenge facing the press, in addition to the financial one. Until that point, “I never felt that the most powerful person in the world was going to be seeking to subvert the role of the free press in this democracy,” Baron said.

One afternoon in February 2017, Trump deployed his Twitter account to declare that the “FAKE NEWS media” is “the enemy of the American people.” That critical moment convinced Baron that there would be “no limits to his attacks on the press, that he would seek to vilify us in every conceivable way . . . to not just discredit us, not just to marginalize us, but to actually dehumanize us.”

Just as alarming was Baron’s realization that no one was rushing to defend the press — not even its own leaders. “As communicators, we were remarkably terrible at communicating our role in this democracy,” he said. “And it was unfathomable to me.”

Soon after, Baron delivered a response to Trump’s declaration of war. “We’re not at war with the administration, we’re at work,” he said at a conference that month. “We’re doing our jobs.” It was a message he would continue to build upon in speeches and statements.

“Every one of you has a stake in this idea of free expression,” he told the graduating class of Harvard University last spring. “And you should acknowledge this if you value these freedoms that come with democracy: Democracy cannot exist without a free and independent press. It never has.”

Reflecting on the two men who shaped much of his editorship at The Post, Baron contemplated what would he have done without Bezos or Trump.

Even without Bezos, Baron maintains that The Post would have deepened its focus on accountability work. But he would have been forced to continue to trim staff and coverage areas. When Bezos bought The Post, Baron was contemplating having to cut at least 50 newsroom jobs in the coming year, he recalled.

And without Trump?

“Even if Hillary Clinton had been elected, there would have been plenty to investigate, and we should have been in a position to investigate,” he said. But Trump, he acknowledged, had an unexpected effect of fueling an intense interest in the news.

“Would we have generated the subscriptions we did without Donald Trump? Probably not, to be honest,” Baron said. “But I think it’s largely now a result of people recognizing that there needs to be a vigorous press in this country . . . that without the traditional press, you’re going to have all sorts of flaky sites spreading falsehoods, lies, misinformation, disinformation, bizarre conspiracy theories, things like that.”

And The Post “fulfilled our mission of holding power to account,” he said. “I’m proud that we did that, notwithstanding the incessant and malicious attacks on us over many years and notwithstanding the assault on objective fact.”

In Baron’s final year in Washington, unexpected leadership challenges emerged at The Post.

The racial justice demonstrations erupting in American streets echoed inside news organizations across the country. At The Post, staffers pressed management to address what they argued were disparities in the hiring, training, promotion and pay of journalists of color. Baron and Publisher Fred Ryan announced the creation of more than a dozen new positions to cover race and related issues.

Still, “if I look back, I would say that I should have tried to do more over the course of my time here and do it more quickly,” Baron said. “No matter how old we are, we all have things to learn.”

And in a couple of incidents, Baron clashed with younger journalists over social media posts that he felt were inappropriately combative or opinionated. It was a stance that some critics within and outside the paper complained was out of touch with the expectations of today’s online discourse.

Baron said his position came from his belief that “we are an institution” and that every Post staffer is naturally viewed by the public as a representative of The Post. “And any statement, any behavior on the part of our people who work on the staff can reflect on the institution as a whole and, in fact, does.”

He added that the number of staff social media posts he has deemed problematic is “infinitesimal,” and that on his watch, the number of formal actions The Post has taken to warn a staffer about such posts was “in the single digits.”

As The Post searches for Baron’s replacement, Cameron Barr, a longtime reporter and editor whom Baron named a managing editor in 2015, will serve as acting executive editor.

The Post marked Baron’s departure with a video tribute to him on Thursday featuring A-list personalities and newsroom colleagues. Among those offering toasts to Baron were NBC News anchor Lester Holt, film director Steven Spielberg, “60 Minutes” correspondent Lesley Stahl and actor Liev Schreiber, who portrayed Baron in “Spotlight.” CNN’s Wolf Blitzer played anchorman for the video, which was produced by The Post and included an unexpected cameo from fashion designer Diane von Furstenberg, who said she bonded with Baron when they were seated next to each other at a dinner. “No one like you is from Tampa!” she recalled telling him when he mentioned his Florida roots. They soon discovered that they had ancestors who came from the same town in Eastern Europe. As a Post reader, she added, “I am sorry he is leaving.”

Naturally, there was a testimonial and praise from Bezos, who credited Baron with making The Post “swashbuckling again.”

Paul Farhi contributed to this report.