A Decade Ago, Jeff Bezos Bought a Newspaper. Now He’s Paying Attention to It Again.

During his tenure as editor-in-chief of the Washington Post, Martin Barron ran into deep problems.

Jeff Bezos bought the Post for $250 million in 2013, less than a year after Barron took over. Bezos, who reached media ownership after founding Amazon and restructuring online shopping, wanted top editors to transform the paper from a regional news organization into a truly global news organization.

But Mr. Bezos didn’t believe the Post would need to add many new editors to accomplish its task, as its representatives were keeping an eye on the budget. Reporters were classified as “direct” employees and editors as “indirect” employees, and his preference was to keep the number of “indirect” employees low.

So Barron has devised a workaround, according to his forthcoming memoir.

“To avoid creating fear, Congressman and I have decided, wherever possible, to remove the word ‘editor’ from proposed new positions,” Barron wrote. “‘Analyst’ and ‘Strategist’ were one of the limited workarounds.”

These days, Mr. Bezos is getting more familiar with the news industry. And in recent months, he has become more involved in running the post, intervening in staff morale and business woes.

Mr Bezos Said He wants the Post to be profitable, but it’s unlikely to hit that target this year.

The Post is on pace to lose about $100 million in 2023, according to two people familiar with the company’s finances. Two other people briefed on the situation said the company expects to underperform ad revenue projections this year. They spoke on condition of anonymity to discuss internal financial matters. The Post has struggled to grow the number of paying customers since its digital subscriber base peaked at 3 million after the 2020 election. It is now about 2.5 million people.

A spokesperson for Bezos declined to be interviewed. The Post’s interim chief executive, Patti Stonesifer, said Bezos was happy with “every dollar invested” in the company. A person familiar with Bezos’ plans said the Post planned to make 2023 an “investment year.”

“I am very enthusiastic about what the Washington Post can do over the next decade,” Stonecifer said in a statement. “Jeff’s 20 years of ownership of the Post should be even more exciting.”

Bezos’ acquisition of The Washington Post marked a new era of expansion under one of the world’s most famous entrepreneurs, ending decades of ownership by the Graham family, which has run the paper through its legendary coverage of Watergate and Pentagon documents. In a meeting with staff shortly after the acquisition, Mr. Bezos encouraged Post employees to experiment digitally with the “gifts of the internet,” such as the global reach that made Amazon so phenomenally successful. He provided sufficient financial support to expand the newsroom.

Bezos weighed the product decision and hired former Politico CEO Fred Ryan as publisher to replace Catherine Weymouth, a Graham scion. He kept Mr. Barron as the newspaper’s top editor until his retirement in 2021, and frequently called on Mr. Barron as the best journalism tutor his owners could ask for. He helped select Sally Busby to succeed Mr. Barron and invited her to her home in Washington’s posh Kalorama district.

But after his decision to step down as Amazon’s chief executive after an initial surge of interest that lasted several years, the Post reported that Bezos took a step back, according to two people familiar with Bezos’ correspondence with the press.

Things changed after Mr. Busby met with Mr. Bezos in January and delivered an urgent message that the Post’s morale was waning. Two people familiar with her remarks said much of it stemmed from missteps by the newspaper’s chief executive, Ryan.

Mr. Busby and Mr. Ryan had a troubled relationship. He accused his chief of staff, Cameron Barr, of leaking information about the Post’s operations to the media and called for his dismissal, according to three people familiar with his remarks. Through a spokesperson, Ryan denied accusations that Barr leaked information and tried to get rid of him. The newspaper declined to comment on the situation. Two people familiar with the matter said there was no evidence to support the leaked claims.

Many Post employees were frustrated by Ryan’s sophisticated business culture and took their concerns to Busby.

Post paper was also full of talent. Last year, several high-profile reporters, including Pulitzer Prize winners Eli Suslow, Robert Samuels and Stephanie McLamen, retired, along with top editors including Barr. Steven Ginsberg, longtime editor. David Maritz, Senior Cultural Editor. Deputy Editor-in-Chief Sharif Dharams.

There have been similar leaks among Post executives, including Chief Information Officer Shailesh Prakash. Joy Robbins, Chief Revenue Officer. Kat Downes Mulder, Chief Product Officer. and Chief Communications Officer Christine Collatti Kelly. (Mr. Robbins, Mr. Suslow, Mr. Maritz, and Mr. Ginsburg have joined The New York Times.)

Bezos made a rare appearance in the newsroom in January. He was present at the morning press conference and met with several Post reporters later in the day. At several rallies, several post office employees expressed concern about Mr. Ryan’s missteps and the direction of the paper.

In June, Ryan announced his resignation and told employees he planned to launch the Center for Public and Civil Affairs, a new project for the Ronald Reagan Presidential Foundation, of which he is chairman. Bezos agreed to fund the center.

Ryan said in an interview with The Times last month that he had “a lot of conversations” with Bezos about the new organization.

Bezos appointed his friend Stoneshiffer, who has served on Amazon’s board of directors for more than 20 years, to run Post in Ryan’s absence and as interim chief executive while the company’s search for a permanent CEO is ongoing.

Stonesipher, who doesn’t get paid for the work, has already started stamping the Post’s stamp of approval. She frequently meets with staff to ask for their input on ‘flowers’, something people are proud of and want to keep growing, and ‘weeds’, issues they want people to address.

On July 11, she and Ryan hired Times and CNN veteran Alex McCallum as the Post’s chief revenue officer and named Vineet Khosla as the paper’s chief technology officer. Stonesifer also repeatedly told staff that Bezos is fully committed to the business and sees the newspaper as a legacy to her family.

Bezos gave his personal opinion on an experimental project being developed for the Post’s opinion section. The project is run by former Bloomberg editor-in-chief David Shipley, who he helped recruit. The initiative, which has yet to be officially named, seeks a forum where readers in cities across the country can post their own opinions and commentary.

Bezos has told people close to him that the new effort, which is being developed with the help of former New York magazine editor Adam Moss, is an opportunity to reach readers who may have missed the news, according to four people familiar with the effort. Bezos meets regularly with Shipley to discuss projects.

Other changes planned for the Post include a reboot of its 54-year-old style section in September. The overhaul will include an online redesign, according to three people familiar with the plan.

Ryan’s departure is seen by employees as a win for Busby, but his relationship with the Post’s newsroom has at times been strained since he joined the company from The Associated Press two years ago. The Post continued to provide high-quality journalism, winning two Pulitzer Prizes for its reporting in May and a book written by two Post reporters winning the Best Overall Nonfiction Award.

According to newsroom sources, Mr. Busby now meets with Ms. Stonesifer regularly and appears energized by the collaboration, and is encouraged by the close relationship between Ms. Stonesifer and Mr. Bezos.

“There’s a sense of hope that we haven’t felt in a long time,” said Sally Quinn, a longtime Post reporter and widow of former Top Editor Ben Bradley.