This article is part of The Poynter 50, a series reflecting on 50 moments and people that shaped journalism over the past half-century — and continue to influence its future. As Poynter celebrates its 50th anniversary, we examine how the media landscape has evolved and what it means for the next era of news.

For years, The New York Times has been a juggernaut in the troubled newspaper industry — profitable and beloved by Wall Street, 10 million digital subscribers, a newsroom that has grown to more than 2,000. But back in 2009, though still making money, business was stalled, and the Times faced a looming debt-refinancing crisis.

Worst case, the Times could have sold the company, as owners of The Wall Street Journal and The Washington Post chose to do. With the unshakably committed Sulzberger family in control, that was not going to happen.

Instead, the Times accepted a $250 million, 14% loan in January 2009 from Carlos Slim, a telecommunications mogul who was the richest man in Mexico and, by Forbes’ reckoning, the richest man in the world at the time.

The terms would be tough. Besides that high interest piling up over a term of six years, Slim was given an option to buy a huge block of stock at a future date. He locked in the rock-bottom share price, then just $6.35, meaning he could buy low and sell high if things turned around. Assuming the Times pulled through, the shares would trade higher — probably a lot higher.

“It was a very stressful time frame,” Tony Benten, senior vice president and company treasurer, recalled in an interview. “We could have gotten a better rate,” Benten said, “but the(ir) terms were much more restrictive,” potentially tying management’s hands just as it was in the early stages of carrying out a broad digital transformation plan.

Arthur Sulzberger Jr., then the Times’ chairman and publisher, declined to be interviewed. But there are clues to how personally difficult the moment was for him.

Adam Nagourney, in his 2023 corporate history, “The Times,” offers this description:

The worry began to wear on Sulzberger. It was visible in the slump in his shoulders, his blank stares into the distance, the unfinished sentences. He had never been good at hiding his emotions, and that mattered now: these were the clues reporters were watching for when they encountered him in the elevator or the cafeteria.

Michael Golden was also worried about the future of the company. But he would remind himself to pep up as he walked out of the subway every morning, and he shared that advice with Sulzberger. You can’t walk around like the world is coming to an end, the publisher’s cousin told him. If you look worried, everyone in this place is going to panic.

With Benten’s help — and some verified number crunching of my own — I’ve pieced together how the company bought itself time, and eventually, a comeback.

The Times had long been the most consequential newspaper in the country — profitable, acquisitive and ambitious. The financial challenge it faced in 2009 was humbling. The loan could have gone sideways. Instead, it bought the paper time to restructure and reinvent, setting the stage for a digital powerhouse that now spans journalism, games, recipes and more.

The problem

In the middle of 2008, Wall Street was cracking. The biggest U.S. investment banks were in desperate shape, and the government scrambled over a single weekend to bail them out. The shock spread globally. Panic set in. The stock market lost half its value and a deep recession set in. It looked as if it might be a long one.

The Times was not in danger of going out of business, but prospects looked bad in 2009, Benten said. The big threat was advertising decline. Financial prestige announcements of initial public offerings and mergers and acquisitions (also known as tombstones) would dry up. Other more important categories for the Times, like technology and luxury goods, looked weak, too.

March brought a 5% temporary pay cut; October brought the elimination of 100 newsroom jobs.

The Times also had a big strategic problem of its own making. The last years of the 20th century were a time of diversification. It had acquired a regional newspaper group and The Boston Globe, made TV and radio investments, and even purchased a stake in the Boston Red Sox and associated media.

But it was time for a 180-degree shift to relentlessly focus on building the Times itself, with the centerpiece a gradual and expensive shift to digital news first. Being pinched for cash was a distraction compared to what needed to be done.

The loan and asset sales

By 2009, interest rates had dropped sharply — good news for homeowners and mortgage lenders, where the crash had hit hardest. But few banks, even the big ones, were willing and able to lend to businesses like the Times. So to get the cash, the company had to agree to a sky-high interest rate in the double digits.

The Slim loan was not a full solution, Benten added. The Times also sold a portion of its new and flashy 52-story headquarters in midtown Manhattan, opened in 2007, for $225 million and leased back the space it needed.

The sale of non-core assets continued. Among the biggest were the Red Sox, New England Media and About.com, a news and reference site organized by 500-plus categories, that sold for $300 million.

In 2013, the Times liquidated its worst investment ever, The Boston Globe, for $70 million. The Times had paid $1.1 billion for it in 1993.

Those sales allowed the Times to pay off the Slim loan early — after two years and seven months — and refinance at a lower rate. Slim’s profit was roughly $90 million.

The warrants

The loan wasn’t the sweetest part of the deal for Slim.

He didn’t fully exercise the warrants, his option to buy stock at $6.35 a share, until January 2015. By then, shares had almost exactly doubled from his set price to $12.60. His 16 million shares gave him 17% of the company’s public stock. On paper, he had earned roughly $100 million.

No wonder Slim is the richest man in Mexico.

Slim held the stock. Over the years, its value kept increasing — to $23.25 in January 2018 and $32 at the start of 2020, the year Slim sold the last of his stake. Remember: He bought $100 million worth at $6.35. The last of the sales yielded more than five times that. His gains on the warrants easily doubled or tripled his $100 million investment.

Mexican billionaire Carlos Slim gives a press conference in Mexico City, Monday, Feb. 10, 2025. (AP Photo/Marco Ugarte)

Big lenders and minority owners of large blocks of stock often seek a seat on the board to influence management decisions. That was not a term of the deal with Slim, and he and his representative never did.

In a Time magazine special issue highlighting the world’s 100 most influential people, Arthur Sulzberger Jr. profiled Slim, three months after the loan had closed. Slim is a model of responsible capitalism, Sulzberger wrote:

“As he spoke at (a get-acquainted meeting with management), he conveyed the quiet but fierce confidence that has enabled him to have a profound and lasting effect on millions of individuals in Mexico and neighboring countries. Carlos knows very well how much one person with courage, determination and vision can achieve. And I am delighted that he brings those attributes to the New York Times Co., to Mexico and to the world.”

The solution

As the economy improved and the Times rebuilt its capital, a series of events propelled it to its current position, stronger than ever financially and editorially.

In 2014, A.G. Sulzberger, Arthur’s son, wrote an influential internal Innovation Report arguing that a lingering print-first culture was slowing digital change. He succeeded Arthur Sulzberger Jr. as publisher of the Times in January 2018, and later became chairman in 2021.

Mark Thompson, who had been the top executive at the BBC, was installed as Times CEO in 2012. Under his leadership, the Times’ digital footprint and international subscription strategy grew steadily.

Thompson hired Meredith Kopit Levien, an advertising and strategy specialist, as his chief deputy. She succeeded him as CEO in 2020. Kopit Levien has continued to oversee fast digital growth, last year reaching the once impossible-sounding goal of 10 million paid digital subscribers. The Times’ specialty sites — Cooking, Games, Wirecutter and The Athletic — have become central to that growth. Users can buy them à la carte or in a bundle with news.

The newsroom has grown to more than 2,000 journalists. In 2024, profits hit $351 million before taxes. As of Wednesday, shares were trading at $48.64, up sevenfold from what Slim paid.

Over the years, Slim diversified from his phone company roots, starting or buying numerous companies. At age 85, he remains an active investor. Earlier this year, Elon Musk retweeted a post on X, saying anyone who is that wealthy in Mexico must have some relationship with the drug cartel. Slim, already on the outs with him, canceled a three-year $22 billion investment in Musk’s Starlink the next day, saying he would build new telecom infrastructure in Latin America through his own companies.

The significance

Then and now, the Times avoids words like desperate or rescue to describe the debt deal. But in his annual State of the Times speech to employees in 2020, A.G. Sulzberger acknowledged its importance.

Noting that Benten had written a $246 million check, paying off the real estate portion of the debt, he said:

This was a milestone we worked a decade to achieve. And it was a fitting capstone to what could fairly be described as our best year in the digital era. …

To be sure, we are not done transforming this 168-year-old company. We still have to contend with the ongoing shift from print to digital, upheaval in the advertising market, the outsized power of the tech platforms, the decline and polarization of trust, the surge of viral misinformation and attacks on a free press. Though The Times is moving forward with growing confidence, our progress is still fragile.

But take the long view. Look at the two and a half decades since we first published on the web. Look at the decade since the financial crisis, when we made the hard decisions necessary to keep Times journalism strong in our most perilous moment. With that broader horizon, Tony’s $246 million dollar check may be remembered as the moment when we officially closed the book on one difficult chapter of our history and began a new one filled with promise.