Long before he was an M&A king, Bruce Wasserstein was a cub reporter. As an undergrad at the University of Michigan, he was the executive editor of the Michigan Daily, the school newspaper—a role that helps explain his devotion to print media. In 1997, he put together American Lawyer Media, a group of publications that includes American Lawyer, the National Law Journal, and New York Law Journal. There were 33 titles under the American Lawyer Media umbrella by the time he sold it in 2007, for $630 million. (See main story.)

In 1999, he launched the Daily Deal, a newspaper devoted to the financial industry, which has morphed into a website and a newsweekly. (View related slideshow.)

The media buy that brought him the most attention was his purchase of New York magazine in 2003 for $55 million. He came in at the 11th hour to outbid a group that included Mort Zuckerman, Harvey Weinstein, and journalist Michael Wolff.

The magazine is officially owned by a family trust in the name of Wasserstein's children, including Ben, Bruce's son by his second wife, Chris Parrott. This made for an awkward period during which Ben worked as an associate editor at New York (he is now an online editor at the New Republic), as he was also, at least nominally, an owner of the magazine. "It was sometimes a little strange," recalls a New York senior staffer. "You could never tell if his agenda was as an associate editor or as the owner." The editor adds that "Bruce was interested in what we wrote about other rich guys, and he is squeamish about getting into their personal lives, but that's because he is so protective about his own."

Adam Moss, New York's editor in chief, says he and Wasserstein "don't talk much about our stories. If he has concerns, he mostly doesn't share them with me."

The move that perhaps is most revealing of Wasserstein's faith in old media came in 2005, when his investment fund paid $385 million to Primedia for 70 trade publications, including Fire Chief and Ground Maintenance.

Wasserstein is an avid reader of magazines, commenting recently about a national newsweekly, "It was the worst single issue of a magazine I have ever read." Moss says his boss likes the feel of magazines, "likes to hold them." Moss says Wasserstein so misses New York on its off weeks after double issues that he asked why Moss does 46 issues a year instead of 52. Moss told him he'd lose money on those six issues.