Illustration by Kathryn Rathke
Illustration: Kathryn Rathke

As a trial lawyer, you won’t always succeed. You just won’t. It is truly OK to fail. But recognize that when you do fail, you are a loser. And don’t pretend you’re not.

Growing up in a tiny rural community in downstate Illinois teaches you a lot about life. We didn’t have a pot to pee in or a window to throw it out of. I believe that you should show respect to everyone you encounter, and that everyone has value. You can’t be rude to anyone. And if you think you can, then you’ve got to reevaluate your life.

The Jussie Smollett case came along somewhat unexpectedly. I was actually in a line for Space Mountain at Disney World with four grandkids driving me crazy when I got the call. I’ve taken five other special prosecutor roles over the years. I tend to, as my friends say, tilt at windmills. Meaning that I get bored sometimes, and if something interesting comes along, I just say, “Yes, I’ll do that.”

Egos are a major enemy of lawyers. You have to believe you’re better than everyone else in that courtroom. But you cannot show that. I don’t want a jury to say, “That guy Webb was cocky.” I’d rather they say, “Wow, that guy Webb was confident. Sometimes he was very soft-spoken, but he always knew what he was doing.”

Things never go smoothly. The witness never stays on track. They always take you off on adventures, and your mind has to be racing: Now that he answered it that way, what is my next question? You have one nanosecond to figure it out. If you’re going to be a good trial lawyer, that gap between your brain and your mouth has to be small.

No, I don’t feel sapped afterward. When I was a kid, I worked on farms. You’re baling hay in 130-degree temperatures, and after two hours you can’t breathe and you actually may die, and your uncle says, “Fuck you. Just keep baling.” That was way worse.

Sometimes you just make a mistake. In planning the cross-examination of Judge John Murphy in the Operation Greylord case, I had decided I needed to show him respect because he had worn the robe. But the first hour, it just wasn’t clicking. At recess, two of the lawyers trying the case with me said, “We’re losing.” So the next day, I came out of the box in a very aggressive way. It was the same with Ronald Reagan during Iran-Contra. I thought the jury would resent it if I took him on. But at the end of the first day, I realized: This is not going well. That night, I stayed up and redid the whole cross-examination.

I’ve been a runner for 50 years. It helps me get in touch with myself. Everything just seems to unscramble. It’s like a vision.

I’m a huge believer in listening. Life is just better if you listen to what other people say. I want to understand what’s going on and whether I might be mistaken in my view on some major issue. But listening does not come naturally to me. I am a classic type A, and the most classic symptom is interrupting other people. Because my mind works very quickly and I chug through facts, I’m in meetings all the time thinking, Holy shit, would you please get to the point? But I just let them say what they want to say.

I have taken on controversial clients without any hesitation. People have the right to a lawyer, regardless of what they’ve done. But if I said there haven’t been limits, I wouldn’t be truthful. I would never become involved with someone accused of sexually abusing children.

A year or two ago, I was asked to represent Donald Trump. I was honored, but there were voices that did not feel comfortable with the firm representing him. I was resisting that to some extent. But then I realized that what I do as a trial lawyer would change drastically: Is a company going to want me to be in front of a jury when half the jurors will hate me?