This post is a response to the question: “What living person would you have dinner with if you could choose anybody?”
I ruled out current role models I already look up to because to use my magical summoning power to have dinner with someone I already know seemed wasteful. My final choice was not the most famous person I considered; nor the most talented; nor the smartest; he is not even the most difficult to actually get in touch with among the dinner partners I considered (that would be you, Dalai Lama). If I could have dinner with one person, I would chose Bill Simmons: Editor and columnist for Grantland.Com, former ESPN columnist, author, and host of many sports related podcasts and talk shows.
I chose Bill Simmons over my other finalists (Malcolm Gladwell, Desmond Tutu, Dalai Lama, Donald Glover) because he has been a large part of my life for many years. he has been my undisputed favorite sports writer for as long as I can remember (Stephen A Smith’s days as a writer for the Philadelphia Inquirer were always a close 2nd place). He is passionate about his work. He has amassed an incredible amount of information and stories about the sports world, specifically the NBA, which I am very passionate about. He continues to be on the forefront of creating new types of content (ESPN’s 30 for 30 series), and more than anything he is entertaining, thought provoking, and has been my favorite read on the internet my whole life.
I imagine Bill and I would dine at a steakhouse in LA or Boston: a meal that should give us plenty of time to talk. I would want to hear anecdotes about Magic and Bird, about Michael Jordan, Allen Iverson, and Pedro Martinez. I’d want to hear about the times he’s had with Jimmy Kimmel that they can’t joke about on air. I’d trade opinions with him a wide range of topics from sports, to movies, music, and general theories on life. I’d want to hear what he’s working on next.
As much as I would enjoy the dinner itself, I would be happiest if I were able to translate our meal into a continued relationship. I would love to enter Bill’s inner-circle: to learn what he is working on next, to be able to be a fly on the wall and hear about the time he spends with superstar athletes and personalities, to be able to shoot him a text or an email when I see something on TV that I have to tell somebody about immediately.