Actually, he's an attorney by training (Harvard law). Clerked for Supreme Court Justice Potter Stewart and in the early years of the Reagan administration, worked in the Justice Department alongside Rudy Giuliani and Kenneth Starr. After that he became a partner at Sidley & Austin, the blue-chip law firm. Hiller, who grew up in Chicago, joined Tribune Co. in 1988 as its top in-house lawyer. Then he moved up the ranks - senior vice president for development, president of Tribune Interactive and senior vice president of Tribune Publishing. He got the job as Chicago Tribune publisher when Scott Smith took over as president of Tribune Publishing (Smith is the guy who gave Jeff Johnson the boot). He's been on the fast track at Tribune for a while. Tribune CEO Dennis FitzSimmons made a big deal of his work as head of the Interactive unit. Here's a nugget from a 2005 Chicago Sun-Times piece:
Hiller wants to make the paper more inviting. The paper now regularly previews feature, celebrity and sports stories in a space above the masthead on Page One, which Hiller calls "the Skybox." And, according to sources at the paper, Hiller has told editors to give stories with popular appeal better play. "I think we're seeing there's opportunity, still, to have a variety of lead stories on the front page," Hiller said. As an example, Hiller cited a recent story by entertainment reporter Mark Caro on a chefs' feud over foie gras, or duck liver. "It was a wonderful story, was played on Page One, above the fold, was a story that really had people talking," Hiller said.
*More stuff: A few months back the Trib started selling ads on the back of its weekday main news section and the front pages of some sections (as many papers have started doing). “What we are trying to do is be innovative and create value for both readers and advertisers,” he told Crain's Chicago Business. Tribune has had it own challenges with revenue declines; ad sales fell 4 percent in the second quarter. In a memo explaining the change in ad placement policy, Hiller said, "I will emphasize that none of these new ad positions in any way compromises any journalistic values, nor would we consider anything that did."
Like many major papers, the Trib has had its share of jobs cuts, too. In July it announced plans to slash about 120 positions by the end of the year. Of those, 80 will be job cuts and 40 will be open positions left unfilled. Tribune weekday circulation edged up 0.9 percent, to 579,000, for the last reporting period ended March 31. Sunday circulation was up 0.4 percent.