Rosecrans Baldwin is a writer and regular contributor to GQ. His latest novel is The Last Kid Left.

“It requires a lot of preparation in order to just have lunch with Roger Federer. Being a person who tends toward anxiety and also a former Boy Scout—put those two things together and I will exhaustively prepare so that I can come across like a complete idiot. The idea of sitting down with someone like that is that you should know everything about their life and their career so that you can go in with 12 questions in the back of your mind.”

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The Exile of Rick Pitino

In 2017, the Hall of Fame Louisville coach’s career collapsed under a string of scandals, leading to his firing from the school he had coached for 16 years. Now, Pitino is finding himself in Greece, coaching Panathinaikos, working for a self-styled Bond villain, and enjoying a new chapter of his life.

Playboy Interview: Steven Jobs

Steve Jobs, age 29.

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"It’s often the same with any new, revolutionary thing. People get stuck as they get older. Our minds are sort of electrochemical computers. Your thoughts construct patterns like scaffolding in your mind. You are really etching chemical patterns. In most cases, people get stuck in those patterns, just like grooves in a record, and they never get out of them. It’s a rare person who etches grooves that are other than a specific way of looking at things, a specific way of questioning things. It’s rare that you see an artist in his 30s or 40s able to really contribute something amazing. Of course, there are some people who are innately curious, forever little kids in their awe of life, but they’re rare."