That said, he was a great character to cover. He had some real accomplishments as mayor—I think he did behave well in the immediate aftermath of 9/11. As I say, I had a contentious relationship while covering him, but if you see somebody as purely just a creep, then frankly they’re not very interesting to cover. Deeply flawed characters—and I would certainly put Giuliani in that category with his operatic highs and operatic lows—make for great coverage. So what I did for the Times was a series of very long biographical pieces on him. I was trying to kind of parse out what it is that makes this person tick.

Did you end up discovering what it was?

It’s a challenge, because Giuliani didn’t talk to me; he talked to me all of three minutes over the course of eight months. But one piece I particularly enjoyed writing involved his radio show. Giuliani had a weekly radio show, much as the present mayor does. But the present mayor’s show is soporific and you could fall asleep listening to it. With Giuliani, it was like this bubbling seething id that just held court. He would mock people and he would knock people and he would rip into them. It was riveting.

I had written back in the day about this, but I went back into the city archives and they had every tape. I found an old tape recorder—because that’s all they had, none of this was digitalized at all—and I listened to endless hours of these shows and put together a fun piece. It was just a wonderful window into his id and ego.

And when he eventually fell, you shifted to cover then-candidate Obama. You’ve spoken about the freedom to report. Was it limiting to be part of the entourage following a candidate around?

I’ve always tried to avoid being on the plane, in the bubble, throughout my career. It’s suffocating. My fear coming in [to the Obama campaign] was that you get caught up in the daily story. And, though it’s perfectly collegial and many of the people from the other papers became friends of mine, you’re in this sort of sweaty competition at the same time. I had done this at New York Newsday years before with City Hall and it’s just not me. My tendency is to want to go longer, to zig rather than zag. Part of it’s temperamental. I don’t want to hold myself above it. There are people like Peter Baker, whom I worked with at The Washington Post and who now covers the White House for the Times, who are superb at it, I think. It’s just not something that’s particularly energized me, having done it for a while at City Hall.

How did you approach Obama, about whom and whose campaign so much had already been written?

I became interested in how he was playing in white working class Democratic districts. I picked one county in western Pennsylvania, Beaver County, which is an old steel mill county—it had once been ninety percent Democratic but is now sort of fifty-fifty. The Times gave me the freedom to do it. I went there two or three times during the election for a week, knocked on a thousand doors, just followed my nose and wrote pieces about this stuff. I explored race there, because it was a predominately, though not entirely, white working class area, and people were enormously candid. For better or worse. And honest.

Joel Meares is a former CJR assistant editor.