PLAYBOY: Has Obama been hamstrung by the midterm elections?
O’DONNELL: Yes, and especially now that there are people in Congress whose only agenda is to stop anything from happening. We’ve had a sharp decline in the past 15 years in the education of elected officials. They are being educated in their political and governing views through sloganeering. We’ve produced a class of elected officials who are by far the shallowest in my lifetime. Their entire understanding of what it is they do for a living comes from the talking points put in front of them during their campaign. It’s true of Democrats and Republicans. On the Republican side there are now politicians in office who hate government. You’re electing members of the House of Representatives who are running against government. It’s like saying “I’m running for president of Avis because I hate the car rental business.”
PLAYBOY: Maybe that’s a good thing. Tea Party legislators would respond to that—to use your analogy—they hate the rental car business, and they’re here to fix it.
O’DONNELL: The trouble with approaching government from the standpoint of “I hate government” is that you are extremely unlikely to find a better way for government to do anything at all. You are also extremely unlikely to be the persuasive person on the matter of what the government should no longer do. And it’s even worse because of a horrible dynamic that doesn’t allow a Republican to veer from the right, no matter what he or she thinks. Occasionally a Republican would realize Rush Limbaugh had gone way too far and said something absolutely unconscionable and indefensible, and that Republican would say so, and then Rush would immediately discipline that Republican on the radio, and that Republican would apologize, all within a 12-hour news cycle. That policing system is flawless. And when you have a policing system like that on thought, thought stops.
PLAYBOY: If the media are complicit, and Limbaugh and others are the biggest offenders on the right, you have to be included in the list of the biggest offenders on the left.
O’DONNELL: I’m not policing thought. The opposite. I encourage thought. I want thoughtfulness. I want people to understand the complexity of the issues. Otherwise nothing meaningful will ever change. I want debate. I want people to be educated enough to have a conversation.
PLAYBOY: But isn’t the reality that MSNBC is simply the left’s answer to Fox News? Isn’t that its raison d’être?
O’DONNELL: Not originally. At first MSNBC was trying to be Fox, doing a pathetic imitation of it. In show business you follow the leader, and Fox was the leader. If you have Desperate Housewives, then we’re going to get a housewives show. Fox was this incredible success, just amazing all of us, and MSNBC was trying to imitate it in whatever ways it could, pulling in whatever Republicans it could. The only liberal it hired at that time was named Ron Reagan, and his father used to be president.
PLAYBOY: What changed?
O’DONNELL: It was a wonderful creative accident driven by Keith Olbermann. At a certain point in the progress, or lack of progress, of the Iraq war, Keith, who had his show on MSNBC, took a sharp turn to the left, and the ratings skyrocketed. If those ratings had gone down, that sharp left turn would have been stopped. I’m sure the executive class was afraid of it at first, until it saw the ratings reports. Once it did, there was no turning around. Counterprogramming turned out to be exactly what to do.
PLAYBOY: How much do ratings influence the stories you cover? You’ve said you’d like to talk about Chinese currency on the show, yet you’ve also covered Charlie Sheen.
O’DONNELL: If a story’s out there, and it’s big and it’s news, we may cover it. On a show I was hosting long before this one, the question came up, “Are we going to do the Lindsay Lohan story tonight? Does this belong in our news mix?” There are holier-than-thou audience members who believe Lindsay Lohan doesn’t belong in the news mix, but I said, “Yeah, we can do the Lindsay Lohan story, but we’re not doing any jokes.” This was the same night we were doing a little item about Chelsea Clinton’s wedding that weekend, and I noticed these stories had something in common. What we were seeing in Chelsea Clinton’s wedding and in the latest Lindsay Lohan saga was a story about American parenting, the risks and possibilities. There were two girls, not of a terribly dissimilar age, who grew up with very difficult parents. If your father is president of the United States, no matter what he’s like, he has made your life extraordinarily difficult. It’s a hard way to grow up, and you have to find your way. And you’re doing it in an age of unbelievably intense media scrutiny. Then when your father misbehaves egregiously, in a way that would be difficult for any daughter to bear, you’re going to have to bear it, knowing that everybody you meet for the rest of your life knows that about your father before they meet you. And there was Lindsay Lohan, who is an extraordinary artist, really lovely, in the place she was in—is still in—because her parents chose to put her there. No one can become a child actor without parents saying, “I want my child to become a child actor.” It’s one of the worst things you can do to a child—to put him or her to work that way, to put the burden of movie stardom on a 12-year-old, as she was when she started, and the burden of having hundreds of millions of dollars at stake based on what she does on the set at work tomorrow, to steal childhood from her and then say, “Good luck with adulthood.” It was a terrible, terrible parenting choice. So the story about Lindsay Lohan and Chelsea Clinton that interested me was about their parents. That weekend we were going to see a family, with all the human frailties families have, that did its absolute best under extraordinarily difficult circumstances to provide the best childhood they could for a kid whose father was governor and later president. And then we were watching another couple of parents who cared more about what their child could do for them than they ever cared about what they could do for their child. That’s the story we did.
PLAYBOY: When you spoke about Charlie Sheen, unlike many other shows, which talked about his problems with a sort of prurience and glee, as if it were a joke, you spoke soberly about his mental state and his addiction.
O’DONNELL: You can’t grow up Irish in Boston and not know something about addiction. It is one of the plagues of my culture, so I’ve been through these trials with friends and loved ones, and it’s something you can never joke about if you’ve been close to it. There’s no question what you’re looking at because there’s no original behavior. You’re watching a person dying who may or may not die. If you’ve watched someone die that way, there’s only one way to look at it. You’re looking at tragedy, whether it’s an unknown person from my old neighborhood or a celebrity.
PLAYBOY: Now that you’re a celebrity, how does it feel when you’re the subject of speculations and scrutiny by the press?
O’DONNELL: I have a perverse relationship to untruths about me: I love them. Every untrue thing said about me publicly means people know less of the truth, and that means I still have my privacy. I once told one of the Kennedy cousins about it. I said, “You know, I love it when they get things completely wrong about me, because it means I still have my privacy.” Like other Kennedys, throughout his life he’d fought against untruths about himself and his family. “You mean it’s a good thing?” It was a revelation for him.
PLAYBOY: What’s a favorite untruth printed about you?
O’DONNELL: In the past couple of months it was written that I was some kind of barroom brawler and carouser, which I think is great, especially as it contrasts with my deep dark secret, one I haven’t revealed publicly.
PLAYBOY: What haven’t you wanted people to know?
O’DONNELL: My big dark secret is I’ve never had a drink in my life. I’ve never been drunk in my life, and I’ve never taken a drug.
PLAYBOY: That’s your deep dark secret? For most well-known people, that would be the untruth. Why have you hidden it?
O’DONNELL: That fact would generate a set of presumptions.
PLAYBOY: Such as?
O’DONNELL: It would suggest a tremendous amount of behavioral conservatism, and that’s just not the case. It also would suggest a kind of intolerance, which isn’t the case either. To some people it suggests a kind of discipline that’s absolutely not present. I wish I had that discipline in the face of ice cream. I just don’t have an attraction to the most corrupting and dangerous of consumptions.
PLAYBOY: Did you abstain as a reaction to the alcoholism and addiction you’d seen growing up?
O’DONNELL: Every guy was drunk every Friday and Saturday night by the time he was 11 years old. Most of them started around the age of 10. Everybody was drunk by the time they were 11. By the time they were 12, they were seriously drunk every Friday and Saturday night. Some of them never came out of that. But that’s not why I never did it. I simply hated the taste of it. I had nothing against it. I just wouldn’t put something in my mouth that I hated the taste of. It became a mostly faulty girl-getting strategy. My teenage strategy was, “I’ll be the one who’s not puking. Let’s see if that works.” It turns out the girls in my neighborhood weren’t interested in you no matter what you did, so it didn’t work. I was well into adulthood until somebody said to me, “Well, you know, it can help on a date if a girl has had a drink.” And I went, “Hmm, maybe that’s why I’m behind the curve.”
PLAYBOY: Besides your abstinence and lack of luck with girls, how else would you describe your childhood?
O’DONNELL: As I said, our neighborhood in Dorchester was almost entirely Irish, and I learned one of the most important things about my culture by watching television. I’m not sure I’ve learned anything since by watching television. When I was a kid, Carroll O’Connor, star of All in the Family, was on The Merv Griffin Show, and they were talking about Irish culture. Merv was asking about when O’Connor went back home to his neighborhood after he’d become a success and said, “That must have been the return of the conquering hero.” O’Connor responded, “Oh, you know, the Irish would much prefer you come back in failure.” On my Little League team, the best thing you could do was get a walk. You didn’t want to strike out; that was embarrassing. But the other embarrassing thing would be to hit a home run.
PLAYBOY: Were your parents hard to please like that?
O’DONNELL: They were exceptions. My father was a Boston cop who would sit on the witness stand being cross-examined by lawyers and think, I could do that. And he did. He had to go to school at night, because he didn’t graduate from college, and he became a lawyer. That’s the kind of achievement story that doesn’t belong in my culture. Everyone told him, “You can’t do this. You will fail.”
PLAYBOY: How are you treated now when you go home to your old neighborhood?
O’DONNELL: The good thing about my culture’s alienation from achievement is that people are never overly impressed by it. They never think someone has to be looked up to because of what they’ve done occupationally. They take people as they think they are. If you get some fancy job, they’re going to be looking for you to be a jerk about it, and they expect you to be. And if you’re not, then you’re okay.
PLAYBOY: Even after you went off to Harvard, worked for a U.S. senator, worked in Hollywood and had your own television show?
O’DONNELL: These aren’t people who get impressed. These are people who are never disappointed in a politician because they’re not childish enough to believe what a politician says while running for office. They tend not to be disappointed by a lot of things in life or by a lot of people, because they’re suspicious of appearances and promises. These aren’t people who end up with mortgages they can’t afford in some sort of delusion-driven deals. These are people who tell you what they think, whether you want to hear it or not, which is why this is probably a pretty good job for me. I can say whatever I want about whatever is going on in the world. No one tells me what to say. No one tells me what not to say. No one ever will.