We have a lot to toast to. It’s the 10th anniversary of the Grand Kids Foundation, Grand Giving has raised $3 million and has served 15 million meals to people in need, you were awarded the Roberto Clemente Award last year and this is your third time on “A Drink With.” When I first met you, you were off to the New York Yankees for your first season. How have you changed over the last eight years?

I was 28 years old. I hadn’t touched 30 yet. As Jay-Z says, “Thirty is the new 20.” I left Chicago and Detroit, which were the only two baseball homes for me. Detroit was my second home. I was Midwest all of the way through. I had been to New York to play as an opponent, but living there I’m like, “What am I going to do? Where am I going to go? How much are things going to cost?” To be with such a great group of guys over there — Derek Jeter, Alex Rodriguez, Andy Pettite, Jorge Posada, Mariano Rivera, just to name a few — the adjustment kind of happened easily. A lot of the spotlight was on them, so I could just kind of sneak in and do my thing. Now, eight years later, I’ve been in New York for that long. It’s amazing. Everyone says, “Why didn’t you buy [a place] there?” I didn’t know I would be there for eight years. If I had known, I definitely would have bought something. It would have definitely been more expensive than buying something in Chicago.

Does it feel like the time has flown by?

Now, looking back, it has definitely flown by. It was amazing getting situated and getting to know East Side versus West Side, Midtown versus Central Park— all of these different areas —and now I know them like the back of my hand. People contact me asking, “Where should I go when I go to New York?” I was that person before, trying to find out where to eat, where to stay, understanding that it’s good to go north to south but not east to west because the traffic is so bad. Those are things you learn when you’ve been so engrained in the city like I have.

It seems like your parents instilled in you the importance of giving back. What memories do you have of your mom giving back in the community and where did her passion come from?

I’m not sure where they got it from. I think they realized that they had a lot of help along the way. I know my mom was able to go to college because she received a scholarship. My dad played basketball in college, so that obviously helped him financially. He’s one of 10 brothers and sisters, so I’m sure they were all helping each other out in some way. As a little kid, I didn’t realize they were giving back until now I look back at it. For example, just watching them always invite people over to eat. They would always pack to-go plates to give to people. They were both teaching, so they would take clothes I outgrew to school. There were students that were my size and my age that could fit into these clothes. I was like, “I’m not using this; you can take that.” Now I look back and realize they’ve been giving back my whole life. That was just the way they did it. Even to this day everyone still comes to my house for Thanksgiving to get themselves a plate and take off. My mom makes mac-n-cheese because she knows people are going to come, get that and take it to their next destination.

I admire how you still have this core group of friends from high school. What do those relationships mean to you?

I think people admire the fact that my friendships have been so long. One of the guys I’ve known since first grade. It’s been 30 years now. I have a friend that I’ve known that long, which is absolutely amazing to think about. A couple others I’ve known since fourth grade, some since high school and some since college. These are true friends and they see me throughout the course of the season. I come home and look forward to being with them. They help out at my kids camps, they attend these events, we travel together— all of these amazing things. I look at other people and the relationships they have are fairly recent, fairly new. They don’t have those in-depth, long stories and memories of good times and bad times.

They know the real you.

That’s it. They know it all. We have all of these great stories — both good and bad — from 6 years old all the way until now as I sit here talking to you at 36.

Is that one of the reasons you’ve been able to stay humble and grounded throughout this crazy career and journey?

They definitely keep me in my place— it’s a combination of both them and my parents. I’ve always looked at it as [baseball] is my job. It’s no different than anybody else’s job. Some of the things that I do may be different, but it doesn’t make me any more important than anybody else. My mom was always big into, “Treat everybody the way you want to be treated.” I’m not going to come in and demand things, because I wouldn’t want anyone to do that to me. It’s the same thing with my friends and me. We joke around with each other, we’re serious with each other, we push each other— all of these different things that help keep me in place where I am and have been throughout the course of my life.

With such a demanding career, it’s incredible that you’ve been able to maintain those relationships so well. You know you have a good friend when you can pick up where you left off. 

Case in point… my buddy Jason Torres who I’ve known since I was 6 years old. I just picked him up at the train station this morning. He came in from St. Louis. His family lives out there now. I picked him up, he came to the house; he’s going to be with me this weekend. Someone might be like, “Why didn’t you send him an Uber?” I was right down the street!

When have you been the most insecure in your career?

I think it was a mixture of insecurity and fear— two times that I can really remember. One was getting drafted and realizing that now I was about to play professional baseball. Everything up until that point had just been fun. I didn’t know what that meant. You hear professional and you hear all of these things. My goal at that point was to continue to make it fun. Underneath my hat I still write, “Don’t think, have fun” from back when I was in college. That’s helped me along the way to help tackle those insecurities as a professional ball player. The second time was when I got traded to the New York Yankees. Derek Jeter was on this team. They had just won a World Series. [I’m thinking,] “How do I fit into this mix?” And not only that, my first game as a Yankee is in Boston against the Red Sox. I’ve seen the rivalries, I’ve seen the fights. “Am I going to be able to walk out of the hotel right now and get something to eat or is everything changed and the only thing I can do is order room service?” I had heard that when Derek Jeter was playing there he would order room service and people would send stuff to his room and put, “Go Pedro” — who was a Boston Red Sox player— on [his pizza]. I was like, “Oh, no. I can’t eat. I’m not going to be able to do anything.” The good thing about baseball is that there are so many games. You have to play and you have to play another one and another one. You can’t focus on those things. I think that helps out.

When you’re feeling like you’re in a slump, how do you turn it around?

I talk to my friends and family. Text messaging has been the best thing that I can ever get now. Unlimited data… thank you so much for that, AT&T. My teammates and everyone look at me and say, “Who are you talking to at all hours of the day and night?” I have so many different friends and family, not only in the U.S. but people internationally, that I can just chat with about anything and everything and nothing all at the same time. No one is going to say, “How was that 0-3 last night?”

So you don’t dwell on it?

Not at all. Once the game is over, it’s over. We start talking about a bunch of other things, like catching up on “Martin” re-runs, food, what trip you’re going on or your new baby on the way. I’m very analytical, so I try my hardest not to.

What was more bittersweet, leaving Detroit or New York?

The Tigers is where I started. It was my first World Series, my first All-Star Game and I made it to the big leagues with them. And then I got traded. It was one of those things where I was like, “This isn’t happening. It’s a rumor.” And everyone else knows about it, but I’m not willing to accept it. It happened in the winter and I was actually furniture shopping when it all ended up happening. Next thing you know I’m with a new team. Here we go. The most recent one going from the Mets to the Dodgers… it was just so quick. Getting traded at midnight and then playing in a game at 4 p.m. the next day with a new team and after a flight. It was a whirlwind of things. I get it though. It just shows that in baseball you have to keep going.

You’re entering free agency this year, but what does life after baseball look like? I’ve heard you say that you don’t want to coach.

That’s still the same.

Why is that?

I have a great deal of respect for the coaches I’ve had from the little league to the major leagues. The amount of time and effort to coach and put kids and adults out there in the position to win and the pressure not only from them but the fans, parents, siblings… to try to please everyone is just a little too much. I want to be able to help others— whether it’s mentoring, clinics or being an ear or a voice to help in baseball. But I don’t want to be on the field trying to win and for that to be my job.

I love how you say, “Control what you can control.” Who taught you that?

I think that was a combination of my dad and my mom. You try to take on and handle so many different things. For example, as a kid when my parents would leave in the morning to go to work — they went to work in the city and I went to school in the suburbs — they would leave me at home by myself. I had to get up, get my breakfast, get on the bus and go to school. That’s what I could control. I could cook breakfast, I could put my clothes on and I knew where the bus was. There was no reason to think about anything else or what school was going to be like because I had to do that stuff first. Once that was done, then I could focus on school. I had to make sure my homework was done, stay out of trouble, then come home and do it all over again the next day. Trying to get too far ahead of yourself makes it difficult, and you start worrying about things that might not even come.

It’s so easy to think too far ahead.

Try to slow down and take some time for yourself.

What are the keys to turning a social media following and platform into something that can make a difference like you’ve successfully done with the Grandkids Foundation?     

It’s knowing why you’re able to have the platform you have. I have the ability to do this and I’m blessed because I’m able to play and play at a high level. That was first and foremost. As long as I do those things then people are interested in what number I wear, what uniform, what places I like to eat at and the causes I’m involved in. I had to do what I needed to do on the baseball field first. And then when it comes time to promote an event like tonight and show the difficulties throughout the United States where people don’t know where their next meal is coming from, people will pay attention to it, but it all began because of the things that I did on the field. It’s something that I’ve talked to a lot of up-and-coming athletes about. Recognize why you are what you are, first. Everything else will take care of itself.

You’ve said you wanted to have a drink with Mariah Carey, Martin Lawrence and Jackie Robinson over the years. Has your answer changed?

There are always more people you want to add. You never want to take someone off the list. Here’s an interesting one. I’ve been told that I look like this guy a lot and we have mutual friends and have never met. Dulé Hill was on a show called “Psych” and he’s got a Broadway show that he did in New York for a little bit. Interestingly enough, USA Today ran a picture of the two of us side-by-side and everyone sort of ran with it. We know of each other but we’ve just never met. Common is another one being here in Chicago because of the things that he does in the city. We have a bunch of mutual friends, but we haven’t met. Chance the Rapper I’ve met quickly. We did a show together— “Windy City Live.” It was really brief and it was before he was taking off and before I was taking off. So, I would say Dulé, Common and Chance.

Photography by Kirsten Miccoli in the renovated Commons Club with new executive chef Moosah Reaume.

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This interview has been edited and condensed for clarity.