I met with Penn twice as the campaign was winding down. The first time, in his office in Manhattan, he was frazzled, edgy, juggling e-mails (he gets a thousand a day) and stepping outside repeatedly to take urgent calls from Bill. His suit jacket was rolled up in a ball on the conference table. He seemed a little subdued, at war with himself or someone, the loyal guy who doesn't name names but was clearly mourning the way things were playing out. The second time, in his gleaming white-and-glass offices in Washington, it was over but for the speech, and I hesitate to say he seemed relieved, but he seemed relieved. He was loose, laughed easily, gamely narrating the stories behind all the tchotchkes in his office—the framed photos of him and Nancy with Hillary and Bill, the photo of him deep in conversation with Bill in the Oval Office (when they were discussing one of the more, "uh, sensitive matters"), the "ACQUITTED" front-page impeachment story from The Washington Post, signed by Bill with gratitude to Mark. His office is dominated by a huge fish tank. (At Harvard he used to "breed fish" in his dorm room; it's safe to say he wasn't the BMOC.) In person he is every bit the geeky guy who secretly loves to watch SpongeBob SquarePants. And every bit the guy who coulda, woulda, shoulda won this thing.
GQ: How did you underestimate him [meaning Barack Obama]?
Mark Penn: I think I never underestimated it, that once you had that kind of candidate, that that kind of candidate could be real trouble. And that if that candidate… You know, if Obama won Iowa, it would really change, dramatically change, the situation going forward. And consequently, I really wanted to question Obama as early as possible.
You wanted to hit him harder? Well, I wanted to question the basic underpinning of his campaign… His problems in his campaign were (1) that he didn't have the usual experience of somebody running for president, and (2) that the positions he took on Iraq—you know, that were revered by the press—didn't really hold up when you look through his record in the Senate.
Why didn't you? Well, I started down that road.… President Clinton took on the Iraq back-and-forth. But the rest of the campaign didn't want to tackle Iraq. They always felt that that was a losing proposition for her, and they always pulled it back.
How much of the reluctance to go after him at the beginning was because he's a black candidate? [clears throat] You know, I can't answer that.
But there had to have been some concern about attacking the first black man who was a serious candidate for the presidency. Well, but the word attack is a harsh word. If you point out somebody's voting records, his attendance records, you know, if you point out how they differ with you on an answer of meeting with dictators, you know, that was a prime concern of a lot of people. It appeared to be the prime concern of a lot of people in the news media. Because the normal stories that would have been written about someone just never appeared. The truth of the matter was, there seemed to be an unlimited market for anything on Hillary and very little market for writing a story on Barack Obama and say, for example, his attendance in the Senate. There has still been no story written about something like that—as basic as something like that.
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