Sorkin imagined DealBook as one part of a larger franchise. It would consist of special DealBook sections in the print paper, a blog, conferences, even a $5,000-per-year premium subscription—just the kind of gift horse journalists love to look in the mouth. At the Times, Sorkin has become something of an in-house entrepreneur, pitching revenue-generating ideas at a time when the paper desperately needs new sources of cash. “Maybe it was uncouth, but I was always the guy who was pushing these plans and prospects on people,” Sorkin says. “I’ve had so many cockamamy ideas I would love to have been able to do.”
Sorkin’s original concept for Too Big to Fail was to chronicle the fateful week of September 15 after the government let Lehman go bankrupt, but soon, he widened the interlocking narrative to tell the story of the first year of the financial crisis from the eyes of his CEO sources. The structure of Too Big to Fail is “modeled almost shamelessly on the movie Crash,” Sorkin says. “I thought you could sort of structure each of these various story lines, which seemed to be happening in this almost autonomous, semi-independent way, sort of like Crash does. And of course as the story progresses, they cataclysmically come together and you start seeing the connections between things.”
Sorkin’s golden Rolodex of Wall Street power brokers surely helped his proposal sell. But when he pitched the book, he hadn’t gotten agreements from his sources that they would cooperate. “I had ambitions to do the thing on the record,” Sorkin says. “But someone told me early on that ‘this is not the way Bob Woodward or Jim Stewart would ever do it. You’re not going to get very far, and if you’re trying to get the intimate details of what they said to their wives, you’re going nowhere fast.’ Once I said ‘I’m not going to identify you as a source,’ people were more open than I expected them to be.”
For both Sorkin and his publisher, the project was a high-stakes risk, given that so far, books on the meltdown have failed to become mass-market hits, and Sorkin had always been a short-form writer. According to sources on the paper’s business desk, Sorkin’s writing was often dashed off—understandably so, given the pressures of reporting merger deals on deadline. Earlier this year, Nocera chipped in to edit his column. “He’s my writing god,” Sorkin says.
Sorkin told me that the idea of writing a book initially seemed daunting. “I thought it would be a 350-page book. I didn’t think I could write 350 pages,” he said. Too Big to Fail ended up at 600 pages. Producing the manuscript turned into a collaborative sprint. With only ten months to conduct interviews and produce a 160,000-word draft, Sorkin hired two researchers to compile exhaustive timelines of virtually every newspaper and magazine article on the crisis, as well as prepare detailed dossiers on each of his central characters. In addition to his editor at Viking, Rick Kot, who edited Barbarians at the Gate, Sorkin asked three freelance editors to work on different portions of the book, including former New York Times Sunday business editor Jim Impoco, now at Reuters, and Hugo Lindgren, New York’s editorial director (who had no involvement in this story). Impoco, in particular, heavily edited the book’s opening three chapters.
Sorkin’s editors clearly had a lot of material to work with. Indeed, he achieved remarkable access to the actors at the center of the financial storm. Beginning last fall, Sorkin filled his days with interviews, both for the book and his regular Times work. “I’d had breakfasts before work, some lunches, a lot of weekends. Constant weekends,” he says. “It was talking to people on the phone, in their homes in the city; Greenwich, Connecticut; and all over.” In part, he positioned himself as both therapist and historian. “For some people it was like history,” Sorkin says. “A CEO I sat with came with notes from a Federal Reserve meeting. These notes were better than any reporter’s notes I’d seen in my life … He had drawn out, on the paper, a picture of the table and written on it where everyone had sat. People like that were extraordinary. I had a guy who sat with me, his PR person and lawyer, we did an interview for an hour and a half that was awful. It was going nowhere fast. But I was peppering him with questions, he clearly knew that I knew. There is an inflection point when they know that you know, and you know they know. The CEO calls me back 45 minutes after the meeting and says, ‘Can you come to my house on Sunday?’ I sat with him, and he just spilled the beans. Here he is in front of the lawyer and everyone else doing one thing, and then completely opens the kimono when no one’s there.”