Illustration by Stavros Damos
Illustration: Stavros Damos

Before I went to work for Playboy, I planned to apply to Yale to get a public policy master’s. I felt drawn to go into politics. Even before that, my dream was to wind up either in the Senate or on the Supreme Court. I had big dreams as a little girl.

I was very happy in the years I ran Playboy because Playboy was unapologetically interested in public policy and politics. I didn’t have to be discreet about being out there on issues such as gay rights or abortion.

It’s so deeply disturbing to me that half of the eligible voters don’t vote in this country. We talk about how divided the country is. The truth is, we don’t even know. We just know what the half that voted thought. I’m a big fan of the Australian approach—there it’s required by law that you vote.

I don’t begrudge anybody their coping mechanisms. But there are going to be a number of really important policy matters that the best of us will want to organize to oppose. So marching now to say, “He’s not my president,” I don’t think is very helpful. I worry it dissipates the energy for when we actually need to protest mass deportation or whatever else.

I don’t ever again want a full-time executive job. But I do have an office at Michigan and Ontario, four blocks from home. It’s me and my assistant, Deb. I didn’t like the image of me padding around in a robe and slippers, carrying a mug of coffee in my apartment all day, trying to work.

When I signed the original lease for Playboy’s last offices, the address was 666 North Lake Shore Drive. Then, before we moved in, the management company changed it to 680 because they were afraid it would discourage other tenants, which was ridiculous. People believe we somehow forced that. Au contraire! I always say, “Are you kidding? We are Satan.”


In any endeavor, you have to understand your tolerance for risk. What’s a failure you can afford? At Playboy, I used to have a rule. Instead of the expression “Don’t bet the ranch,” our version was “Don’t bet the mansion.” Don’t do anything where, if it doesn’t work, I have to call up Hef and say, “I found you a lovely apartment in Westwood.”

I have sort of a superrule that former CEOs don’t talk about companies after they leave.

I love to travel. I still do annual trips with my bridesmaids—something we’ve done for 20 years. We go to a different place each time. Last year it was Nashville. When I got divorced, I said, “The marriage didn’t last forever, but bridesmaids do.”

I tried to behave as well as I could throughout the divorce. I made a decision during the worst of it that I would never want to look back and wish I’d behaved better. We see each other periodically. It’s fine.

We should all miss bookstores. They let you discover things.

I’m very lucky to have these genes. Hef’s mom lived to 101 and was really only ill the last year of her life. She was 99 when I got married. It was a beastly hot summer in Chicago, so I said, “We can get you a wheelchair.” She was almost aghast, couldn’t even imagine why I would suggest that. She stayed at the party until 11 o’clock that night. She was very special.

I stay at the mansion whenever I’m in L.A. because it’s the easiest way to see my dad. I was out there two weeks ago, and we played backgammon all day on a Sunday, and I watched him play gin with his guy friends, which he does once a week. His wife, Crystal, is lovely, and is lovely with him. I’d say he’s in very good health and in very good spirits.