"Baseball is this intense subculture that actually doesn't speak very much for the larger culture."
"Above all, recognize that if you have had success, you have also had luck — and with luck comes obligation. You owe a debt, and not just to your Gods. You owe a debt to the unlucky."
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"If you had to point to one thing that made it less likely that the Red Sox would win the World Series, I would say it was those people that go to Fenway Park to watch the games. And then the media around it."
"The pleasure of rooting for Goliath is that you can expect to win. The pleasure of rooting for David is that, while you don’t know what to expect, you stand at least a chance of being inspired."
"As idiotic as optimism can sometimes seem, it has a weird habit of paying off."
"When you're trying to create a career as a writer, a little delusional thinking goes a long way."
"The inability to envision a certain kind of person doing a certain kind of thing because you've never seen someone who looks like him do it before is not just a vice. It's a luxury. What begins as a failure of the imagination ends as a market inefficiency: when you rule out an entire class of people from doing a job simply by their appearance, you are less likely to find the best person for the job."