The art of the tough interview

I thought about the art–and craft–of interviewing after seeing Donald Trump’s response to Megyn Kelly last month during the 2016 Republican Presidential debate. Kelly asked him about statements he had made about the physical appearance of some women he didn’t like, and Trump retaliated by fulminating all over the other networks, referring not so obliquely to Kelly’s menstrual cycle.

In my 50-something journalistic years, and about 8,000 New York Times bylines, I’ve actually interviewed Trump, along with Muhammad Ali, Billie Jean King, one of the Koches, Reggie Jackson, Mike Tyson, and a host of other sometimes difficult subjects.

As a sportswriter, about half the time I was interviewing someone who’d just lost. So sportswriters must have–or at least show–some empathy. And yet you’ve got to ask questions that could be embarrassing or even highlight the subject’s weakness. The point is that you need a response, a quote.

“Did prison do anything for you?” I asked Tyson. He glared at me, and replied, “You’re very clever, my friend. Trying to get me to say something.”

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Well, he was right.

Over many years, and through trial and error, I’ve picked up a few tricks that help to peel away the steely veneers of certain subjects–some lessons, if you will. Diplomacy helped one night in Seattle, for instance, after the New York Jets had just lost a close football game to the Seahawks, largely because punter Chuck Ramsey muffed a punt attempt. When I got to the locker room, he was crying.

“What is it, Chuck, that punt?” I asked solicitously.

“No,” he replied. “How would you feel if the coach said in front of the entire team, ‘I can fart farther than you can punt?’ ” (For the record, the Times declined to use that quote of a lifetime.)

Did prison do anything for you?” I asked Tyson. He glared at me, and replied, “You’re very clever, my friend. Trying to get me to say something.”

Yet I learned, after I took over the Jets beat, that I was becoming increasingly distant from the players I wrote about. I was 40 years old, and they were in their early 20s. And many of them were culturally quite different from me. Here I am, a Jewish guy from Brooklyn, and I’m interviewing guys from some Louisiana bayou, or South Dakota. I went to City College of New York, and I’m trying to hold a discussion with a kid from the Colorado School of Mines. How could I reach them? Have a dialogue in just a matter of seconds, and get them to trust me?

My academic background helped, and the team’s press guide was my friend. It listed not only the player’s hometown and school, but which subjects he studied, his hobbies, select details about his family. As a liberal arts major back in a day when liberal arts majors studied, well, the liberal arts, I found I could converse with almost anybody on a variety of subjects.

And so I’d look for those tidbits that could connect us: Hey, this guy majored in criminal justice, and I wrote a story about ticket-scalping at Madison Square Garden and met a lot of cops. We had something in common, after all. A good opening gambit, it turned out.

Reflecting on all those bylines, all those interviews, all those moments glorious and tense, I have come to realize that people—no matter their status—have a part of them that needs to be stroked. And my job was to find that part.

Lesson No. 1: Sometimes the best way to get an answer to your question is to not ask it.

The Boston Red Sox had a star named Jim Rice, the bane of sportswriters. He hated us. But the paper wanted me to get his take on a teammate, Fred Lynn, who was having a great year.

“Jim Rice?” said a Boston writer. “Good luck. He won’t talk to you. He never talks to the press.”

Well, I went to his locker before a game. I introduced myself and held out my hand. He let it stay there, frozen. “Now what?” I thought. And then I remembered: My 9-year-old son Mark had a Jim Rice-model glove. It was a year old, but I lied a little.

“Jim,” I said, as he ignored me and put on his uniform, “I just got my son a Jim Rice glove, and I don’t know how to break it in. The leather is very stiff.”

He stopped dressing. He reached into the top shelf of his locker and pulled out a glove. “Here’s what you do,” he began, and launched into a nonstop explanation: How you oil it, how you put a ball inside the glove and then tie it all together to mold the glove’s shape. I couldn’t stop him from talking.

“Anything else?” he asked, pleasantly.

“Yeah, I’m doing a story on Fred Lynn,” I said.

“Oh—a picture out of Vogue, the way he swings the bat,” said Rice, my pal. Thanks for that great quote, Jim. It made my second paragraph.

Lesson No. 2: R-E-S-P-E-C-T, find out what it means to your sources.

At about the same time, I went off to interview a young rising tennis star named Martina Navratilova. She also was getting a reputation as a churl, berating officials and being grouchy with opponents. But I also knew that she was hiding from the world (this was the ’70s, after all) her close relationship with her female manager.

I decided to go into territory that, for the era, was somewhat dangerous. I told her I knew she was having a difficult time transitioning to America, that her family still was in Czechoslovakia, and that the Czech government was unhappy she was thinking of becoming an American citizen. I asked her what impact her partner had on her life.

Suddenly, Ms. Navratilova softened, and she spoke of how her companion had helped her psychologically, teaching her how to cope with the daily pressure of being in the spotlight. I think I brought a new element into understanding this great tennis player who was only 21 years old, who was coping with having left her native Czechoslovakia, and whose lifestyle—had it been made public—would not have been understood by most Americans.

Lesson No. 3: To find common ground, sometimes you first need to look to your differences.

On an earlier venture, I was sent to interview Muhammad Ali, who had just changed his name from Cassius Clay when he became heavyweight champion of the world. The papers were filled with his diatribes against the white power structure and his explanations of why he had changed what he called his “slave name.”

Maybe I’ll play my minority card, I thought. So I told him how I was lucky, being white (although Jewish) I never experienced overt prejudice.

“You’re not as dumb as you look,” said Ali. I took that as a compliment, smiled, and we hit it off.

You know, maybe he was right.

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Gerald Eskenazi produced 8,000 bylines in more than 40 years with The New York Times , in addition to writing 16 books. He now lectures on sports and the news media.