Steve Coll, the new dean of Columbia’s Journalism School, spent 20 years as a reporter and editor at The Washington Post, serving as the paper’s managing editor from 1998-2004. CJR spoke to him about the sale of the Post to Jeff Bezos, the founder of Amazon.

What are some of the bigger strategic mistakes the Post made in recent years?

Probably the biggest mistake, at the beginning, was to extrapolate the old model of market penetration—that is, controlling the local distribution system in an era of the Web’s birth. At first, the Post thought that the best way to respond to electronic news was to own the pipe and have a kind of proprietary approach to pushing content to Washingtonians. That was analogous to the role that that the newspaper had come to play after the last of its local competitors, the Evening Star, died. But it turned out that the Web was a much more open system than that, and so there was some time lost working on the old model.

Then I think, fairly early on for newspaper companies, to give the Post credit, they recognized this kind of open architecture had a whole different set of questions that had to be addressed. And the story of the last 15 years is that the Post knew it had a certain amount of time, not infinite time, to try to solve the problem of digital audiences and digital revenue. To Don [Graham]’s credit, he tried everything he could think of. He lashed up with Silicon Valley companies. He started a digital division and tried to keep it separate from the newspaper so the old guard wouldn’t smother it in its crib. He funded some innovation and experimentation when it wasn’t profitable. The one thing he wasn’t willing to do was to take the Post’s brand and go national, or go global, on digital platforms, or by buying a television network or that sort of thing.

I’m not an investment banker, but my own view a decade ago was that the value of the Post’s journalism, its place in Washington, its reputation from the Ben Bradlee era, might create an opportunity globally and nationally—not in print, but digitally and through video. And that was an argument that was had again and again. And the view of the board, and I think of Don, was that it was the regional franchise that created value. That’s where the value proposition had always come from. It was connected to local readers, local businesses, local advertising revenue, and that we had to stick close to that franchise and not attempt to extrapolate it.

And so, they tried. They tried everything they could think of to replace the lost sources of classified revenue, and I think there was a kind of wistfulness in the statements Monday, where you basically hear Don saying, “I think it would be better for someone else to take a try.”

What does Bezos bring to the problems that you’re describing that the Grahams couldn’t, or didn’t, address?

On the positive side he brings a very strong track record in the new data science of marketing and business. He was an early innovator in using Big Data and customer preferences to disrupt incumbent industries. And he’s a quant guy. He understands the power of not just algorithms, which is sort of a broad term—a placeholder for a lot of different kinds of computer science—but really data in all of its dynamic forms for business. He saw a kind of arbitrage opportunity in the book business and other kinds of retail, where he used data to break into industries. And so he brings that expertise, that management culture. Also, by the way, Amazon executes exceptionally well. That may be 90 percent of why they’ve been successful; maybe the data science is less important than we on the outside think. But he brings that track record, that management culture, those insights about consumer preferences and how to monetize them to a problem in local newspapering that is now befuddling every owner of local newspaper franchises in the country: How do you reach and hold audiences through digital channels when they have so many other media choices besides newspapers? And then, when you can hold them in significant numbers, as The Washington Post has—even though its circulation has diminished, its total eyeballs in the Washington area remains very powerful—how do you achieve enough revenue from that audience to pay for the costs of newsgathering as traditionally defined, and how do you keep a newsroom funded and committed to high-quality journalism while you’re trying to solve this equation? That’s the tricky part.

Brent Cunningham is CJR’s managing editor.