Boland: What was your first thought when you found out you had been traded to the Yankees?
Headley: It was mixed emotions. I think anywhere I would have had mixed emotions. When you're somewhere as long as I was [with the Padres from 2007 through July 2014], it's a little sad in a way to leave. But you're getting traded to a pennant race, you're getting traded to an organization with a lot of history, so those were the positive things I was excited about. The whole thing going on with Derek [Jeter], that was cool. There was a lot more non-baseball-related stuff you have to deal with. Trying to find a place to live. I didn't know where I was going to live. I knew I couldn't live downtown with two kids. Initially, it was a little overwhelming.
Boland: What do you remember most about your time with Jeter?
Headley: It was fun to get to know him a little bit, to see how he plays the game. From the outside, you kind of see the persona, but you really don't know what he's like as a person. Then, obviously, the way things ended was storybook. You couldn't draw it up any better. Obviously, it would have been a lot more special if we made the playoffs and kept going, but it was still something I'll never forget.
Boland: What did you learn about New York you didn't know?
Headley: The suburbs are awesome because you can feel like you have a little bit of space but you're still an easy train ride to the city. I'm kind of looking forward to embracing the city now. When I came in as an opposing player, I was kind of overwhelmed with the hustle and bustle of trying to get to the field. Now that we live here, we're going to be there more.
Boland: What are you most looking forward to experiencing in the city?
Headley: The restaurants, the culture, the shows, the talent, the U.S. Open. Those things. There's so much that the city has to offer, I'll never get to experience half of what it actually can offer.
Boland: Which Broadway show do you want to see most?
Headley: I'd have to see a few to know what floats my boat. I always thought 'Phantom' would be cool. It's hard to say [pick one] when you haven't been to one.
Boland: Have you fit in playing in New York better than you thought you would?
Headley: That's a tough question to answer. I know the type of player I am . . . There's nothing flashy or overly special about what I do, it's just the day-to-day grind, and I think to an extent, there's some parallels there with maybe the people that live in New York City. It's a grind, it's an expensive city, they've got extreme weather, those type of things. I think maybe if there's any way I can answer that question, maybe the way I play is somewhat parallel to the way New Yorkers live. But it was two months [last year as a Yankee], so I don't think I've won anybody over.
Boland: Are you on Twitter or any other social media?
Boland: Why not?
Headley: I enjoy having my life away from baseball. There's some wonderful things that come from social media. We had a handle in San Diego for Headley's Heroes [a charity he started while with the Padres] . . . But it's just something else that I don't really need to deal with. I try to make myself available to the media, to the fans when I'm at the stadium, and I hope that they can get enough from me there. I don't feel like I can portray what I would want to portray in 140 characters.