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On May 25, 1994, Arthur Ochs Sulzberger Sr., who had stepped down as publisher of the Times two years prior but was still the company’s chair, was delivering a speech in Kansas City, Missouri, and turned to the burgeoning “information highway.” He didn’t like it much. “Far from resembling a modern interstate,” he predicted, it “will more likely approach a roadway in India: chaotic, crowded, and swarming with cows.”

That same day, back in New York City, Arthur Ochs Sulzberger Jr., who succeeded his father as publisher (which he remains to this day), was also giving a speech about technological change. “If they want it on CD-ROM, I’ll try to meet that need. The internet? That’s fine with me,” he said. “Hell, if someone would be kind enough to invent the technology, I’ll be pleased to beam it directly into your cortex.” It was a line the young publisher liked to repeat. “He said that in my job interview,” says Martin Nisenholtz, who was hired in 1995 as the original architect of the Times’ digital strategy. “Arthur’s notion was that these technologies were principally delivery systems for Times journalism.” When NYTimes.com launched on January 22, 1996, it was updated once a day with stories from the print edition. Like most everything then, it was free to read for anyone in the US with a dial-up connection.

Arthur Gregg Sulzberger, who goes by Arthur but is known as A.G. around the Times, was 16 at the time, and the bulk of what happened next in journalism—the rise of blogs, social media, podcasts, and mobile; the fall of print circulation, advertising, and prestige—happened while he was learning how to be a journalist. He graduated from Brown with a degree in political science in 2003 and started writing for The Providence Journal and The Oregon­ian before joining the Times as a metro reporter in 2009. The financial crisis that coincided with his homecoming so damaged the Times’ advertising revenue that many started to speculate about when the Times would go bankrupt. Though digital advertising increased from an asterisk in financial reports to well over $100 million between 2005 and 2010, it wasn’t nearly enough to offset the $600 million loss in print advertising over the same period. The Times managed to survive through savvy financial maneuvering—taking out a $250 million loan from Mexican billionaire Carlos Slim in exchange for what is now a 17 percent stake in the company; selling its gleaming Renzo Piano–designed Manhattan headquarters and leasing it back from the buyer; shedding assets like About.com and a stake in the Boston Red Sox—but its continued existence was no longer a foregone conclusion. “The former Times executive editor Abe Rosenthal often said he couldn’t imagine a world without the Times,” one critic wrote in The Atlantic. “Perhaps we should start.”

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Over the next few years, finding new digital revenue became the Times’ top business priority, and in 2014, Sulzberger, by then an editor on the metro desk, was tasked with overseeing an internal assessment of the paper’s digital efforts to date. The result was a 97-page document known as the Innovation Report, which found that editors too often said no to programmers and product designers from the technology group. “The newsroom has historically reacted defensively by watering down or blocking changes,” read the report, “prompting a phrase that echoes almost daily around the business side: ‘The newsroom would never allow that.’ ” Initially intended for only a handful of senior managers, most Times employees first learned of the report from a grainy photocopy that was leaked to BuzzFeed; one employee said they cried when they first read it because, as Harvard’s Nieman Lab reported, “it surfaced so many issues about Times culture that digital types have been struggling to overcome for years.”

The BuzzFeed leak was devastating for Sulzberger—“a moment of panic,” he says. “We had written a pretty frank and candid document expressly for a small group of leaders of this organization, and suddenly it felt like our dirty laundry was being aired.” Even worse: It was a Sulzberger, of the Sulz­bergers, doing the airing. Still, he realized within a few days that the public scrutiny had turned an administrative white paper into a media rally­ing cry. “You couldn’t read that report and think that the status quo was an option. Once it’s clear that that is not an option, then the conversation all of a sudden becomes much more productive. It’s not should we change, it’s how do we change.”

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Five recent standouts from the Times’ multimedia expansion.

NYT Politics Bot

An AI-powered chatbot deployed for the 2016 election. Subscribers could type in questions and the bot would offer up-to-the-minute polling data and analysis.

Still Processing

A weekly podcast from Wesley Morris and (WIRED alum) Jenna Wortham about the intersection of pop culture and public policy.

The Fight for Falluja

An 11-minute VR film from the Pulitzer Prize–­winning video journalist Ben Solomon. Viewers “embed” with Iraqi soldiers battling to retake the city from ISIS.

Puzzle Mania

A special print-only section in the Sunday Times last December. It contained the “MegaPuzzle,” a 728-clue crossword that was the largest ever created for the Times.

Race/Related

A weekly email newsletter with features and essays on race and ethnicity in America.