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Q&A with Luis Castillo: “Life is going to throw you curveballs, you’ve got to learn how to hit them.”

Baseball is more than just a game; it has the ability to change lives. Luis Castillo knows that better than anybody else. NYC Tastemakers had the pleasure of sitting down and talking to the best batboy in MLB history, Luis Castillo, who goes by nicknames, “Luigi,” and “Squeegee,” to discuss his amazing eight-year tenure with the Yankees, his love for baseball, and his continued effort to give back.

Q: What made you first fall in love with baseball?

It goes back to my father. He told me a little white lie, and I believed it! He told me he was a professional baseball player in the Dominican Republic, and, at that time, my father was 48 years old, I was nine years old, and I believed his lie. He told me I had to stay in school, and I would be a baseball player like him and that he used to throw 90 miles per hour, and I fell in love. He sat me down and I would watch baseball games with him on TV and even that little white lie, gave me hope, even though he was lying about his career, he gave me hope, and that hope landed me with the Yankees. God gave me a blessing of having a fabulous bat boy career… I look up to the sky sometimes, because my father is deceased, he died of cancer in 1999, but I look up to the sky all the time and say, “if you hadn’t told me that white lie, I don’t know where I would be.”

Q: Did you ever play baseball?

I played! I started off as a second baseman. As a nine-year-old, my [parents] used to go to my games. I was a good fielder, I always had hands, and I could throw far. But I didn’t have the speed, I was short, and I couldn’t hit, I always batted ninth. My glove kept me in games, and [so did] my defense. When I got older, getting to the Yankees, David Cone was the one that taught me and I became one of the elite Bronx Double A Semi-Pro pitchers in the league, I won back-to-back Cy Young’s after that, and I was honored for that, because David Cone would always make me bring the scorecards into Yankee Stadium the next day [after] I pitched. I would leave the scorecard and he [was] like “you had seven strikeouts!” He taught me how to throw a fastball [and] curveball during batting practice, so I became a great pitcher because he was a great mentor.

Q: What first inspired you to want to become a bat boy?

Another funny story because my life was a comedy! Joe Lee, a bat boy, I didn’t know he was, but he was popular in 1996, and he would always throw baseballs up to us during batting practice, because I was a Bleacher Creature first, I was a fan. I would always go to every home game with the Bleacher Creatures, and I would always say his name, I would say “hey Joe Lee!!!!” And I told the lady who ran the 300-person group, Tina Lewis, and she said, “I’ll make your dreams come true, you want be a bat boy?” I thought she was bluffing me, but we wrote a letter to the New York Yankees, and I sent them an 8×10 photo, told them why I was passionate and that I had good grades because that was the Yankee’s criteria for bat boys, to have good grades, stay in school, no absences, because it’s a hard load of work.

So, they never responded, and every year there’s eight positions of bat boys, but there are only like one or two open a year. So, I wrote a second letter in the offseason of 1997, and in 1998, my third letter, the Baseball Operations under George Steinbrenner, wrote back to me. My mom opened the letter, and she almost passed out! She goes, “you got the job!” I called Tina Lewis, and she started telling everybody. The first day, Opening Day, I got my name chanted in roll call.

Q: What’s the meaning behind the nickname, “Squeegee”?

[Derek Jeter] nicknames everybody. He’s the guy that gives you the nickname, and it sticks. So, my first day on the job, I’m just taking it all in, guys I used to see on a baseball card are now in the same room. He was sitting down, I was standing up, [and] I was probably his height [while he was sitting]. I was starstruck! Joe Lee was the one who brought me up to Jeter and I was like, “why do I have to go see Jeter first?” I didn’t understand, it was tradition. So, I went to Jeter, and he’s looking me up and down. He goes “what’s your name, kid?” And I said, “they call me Luigi,” and he went, “you’re Italian?!” I said no, and then he said, “then why the hell is your name Luigi?!” I said, “gee, I don’t know, it’s a neighborhood thing.” And he said ok, he looked me up and down and he goes “that’s it, Squeegee! Because you look like a window cleaner ‘cause your uniform is so baggy, you’re supposed to be a little tight, buddy!” Whoever it was [at the Yankees], they called me Squeegee.

Q: Who starstruck you the most?

Roger Clemons really starstruck me. I looked up to him. My idol was David Cone, before I met him, I always used to wear his number in summer leagues. Cone was easy-going, but Clemons was more laidback. He would wait for you to talk to him first, and he was a cool dude, who was funny, as well. I was always nervous talking to him, even after getting to know him, that’s how cool he was. He was a great guy though, and always took care of the clubhouse guys. He’s a class act. So, him and Jeter [starstruck me].

Q: What was it like spending these days at the stadium with your baseball heroes?

My mother would say, “why are you never home?” [laughs]. They used to even call the house, my mom would even be like, “Jason Giambi just called at 2 a.m. asking for you.” Daryl Strawberry I still talk to this day over the phone. [All the players] used to say, “we would go the park because you put a smile on your face.” I used to catch with every player, the other batboys were there for fame and other things, they didn’t really have passion for the game. I had a passion for baseball and knew their history. So, I would talk to the players like everyone else, I didn’t treat them like a star. I treated the utility guy the same I did Roger Clemons or Derek Jeter. That’s, I guess, what helped the chemistry in the clubhouse. It was fun times, man, in those clubhouses. You were looking forward to the games starting.

[My sons] still have playdates with David Cone’s son, and David and his wife still invite me over to the city, and we spend the day there, sometimes we stay over. We just have fun, we eat dinner, watch movies, play music, nothing about baseball, we just watch our kids grow. I’m so appreciative for David for being my friend these last 25 years.

Q: Can you talk through the day David Cone pitched a perfect game in July 1999, and your involvement in it?

Joe Girardi [Yankees’ catcher] was nowhere to be found, and it was a rain delay. We were playing the Montreal Expos, who are now the Washington Nationals. The equipment manager was being told that play was about to resume, but we didn’t have a lot of time to warm up. The Expos were already warming up because they were on the field. So, David was looking for Girardi, and in the corner of his eye, he sees me with towels in my hand. He yells, “ay Squeegee, you got a glove and a ball?” And I said yes, but [I was surprised because] starters don’t normally talk to batboys on game days. So, I’m shellshocked, and he [yelled at] me to come warmup with him. [As I was going out], the security guard said to me, “you’re one lucky kid!” And then, I’m in the catcher’s position warming up David Cone, my childhood idol, not thinking of a perfect game because he had no partner to warm up with. We’re warming up and he says, “c’mon Squeegee, let’s go onto the field.”

He walks in front of me, and we’re going down the ramp, we’re getting into the crowd now, out of the dugout, and people are cheering for Cone, and then I come out, and nobody knows me, and I’m there with the ball in hand, and David is by the first base, and I’m literally standing in front of home plate. The Expos were warming up, and me and him were just long-tossing for, like, 10-15 tosses, and I’m saying, “please God, don’t let this guy get hurt, everyone’s looking at me.” I take one quick look into the dugout, and I see Don Zimmer, he’s laughing, with his hands over his mouth. When we were done, David gave me a thumbs-up and tossed the ball back to me, I kept that ball not thinking about a perfect game, but about how I [just] warmed up with my childhood idol, and I was gonna let him sign it after the game. Now, the ball is more valuable because he wrote “we will always forever be connected, perfect game – David Cone,” and we got a picture in the locker room and he called me his good luck charm. These days, we talk about how he helped me when I was pitching, and [at that time], he needed my help.

Q: Your role with the team, while you were there, seemed pretty crucial!

I thought I was only going to be there one year, to be honest. But when we won the World Series, the equipment manager said, “good luck, kid, you’ll be around for a while!”

Q: What’s it like to be a part of a team competing in the World Series?

I saw them throughout 82 home games, and I would travel sometimes to areas on east coast trips. I felt like they took the regular season more serious. Before playoff games, they would be playing music, David Wells was the music guy, and they’re all joking around, and I’m like, “we’re about to play in the World Series!” But, once they said play ball, these guys were like men on a mission, like someone stole money from them. They would be so focused and were helping each other out, and I would see those talks, and I was so grateful for that. I got to go to the 1999 World Series in Atlanta, for Games 1 and 2, and the fans were intense, but it didn’t intimidate us. We went in there and did our job [winning both games].

On the plane rides back, we were like little kids, watching movies, I would sit next to David Cone, and joke about stuff. It was like the World Series wasn’t even happening, we were used to it, they were all born winners. All 25 of those guys were born winners. It was amazing to see.

Q: How were you feeling when you were inducted into the Hispanic Heritage Baseball Hall of Fame in 2020?

Some people don’t get to get their flowers alive, and it’s a shame, I feel everyone should get their flowers alive. I didn’t expect it, I got a phone call, and it’s Tito Avila and his brother, and they are the Board owners [of the Hall of Fame]. Just to name a few [people in the Hall of Fame], Roberto Clemente, Ruben Sierra, and Edgar Martinez. So, to me, for a Board, without me knowing, to vote me in as a batboy, and to open up doors for other batboys and ball boys around every sport, and to be a pioneer, being inducted as a Yankee batboy for my contributions on and off the field, was such an honor for me to have. My mother and my family were there, and I cried like a kid. My kids were there, too, it was just a surreal moment. My plaque and my story will forever live in the second highest museum in baseball history!

I couldn’t have done it myself. The credit goes to the likes of David Cone, Derek Jeter, Daryl Strawberry, and Doc Gooden, who would sit me in the clubhouse and talk to me about life. Daryl Strawberry gave me this quote, and I live by this, “it’s not how you start, it’s how you finish, kid.” I always thank him to this day for telling me that, and that if he never told me that, I wouldn’t have had that type of mentality. And with David Cone telling me, “tough times don’t last, everything’s gonna be ok, Squeegee.” These guys were like father figures, and Derek Jeter, I thank him, for teaching me the ropes of giving back and the likes of George Steinbrenner, I want to keep his legacy alive.

Q: Can you tell me about Squeegee Children’s Literacy Foundation?

I helped Derek Jeter with his foundation, and him and Jorge Posada showed me the ins and outs. They would always come to me because they were too busy preparing for a game, and they would go make me take attendance of the players who were going to attend, how much they were donating, and stuff like that. They would invite me to their events, and I would take notes, and I said when I get older, I’m going to save enough money to help kids around my communities in the Bronx. With a lawyer, I wrote a letter to the Albany Senate, and they granted my wish. A lot of urban kids in New York, especially Latino and African American’s, are poor in literacy and reading and that’s due to resources. So, my mission statement for my foundation is to have kids put down their videos games and read 25 minutes a day.

I go to schools and I do motivational speaking. I talk about my baseball career and my foundation. I started with one school, and now I have about 23 schools in New York I go to. This started in 2013, and I’m very passionate and, like I said before, it’s thanks to the likes of David Cone, Derek Jeter, and George Steinbrenner, for showing me the true meaning of what it means to give back because when you give back, you’re not giving back to receive, and George Steinbrenner always said this, you’re giving back to see the smile on that person’s face because it’s gonna make your heart smile. That’s such a true statement!

Q: What types of things does your foundation do to raise awareness?

We do book bag drives, and I have one-on-one meetings with troubled kids that are flunking. I sit them down and explain to them how the future is going to be harder if they don’t listen to their parents and teachers. With some kids, I reward them, I make them a promise, they make me a promise. If they lift their grades or graduate, I’ll buy them a bike or give them toys, or give them a check to take their family out to eat. So, it’s like, you do for me, I do for you. [We] show them the value and importance of getting an education every step of the way, until they finish high school or want to go to college. We just show them that they’re not alone and there are people in the world who care about them.

We do other different things as well, I’m an independent actor for Ray Negron’s play called Bat Boy, we’re in theaters in Long Island. We’re having [some shows] off-Broadway coming soon. Ray Negron and I do different charities, we raised money for kids with ALS, cancer, families that go hungry, education [for Squeegee Children’s Literacy Foundation]. We just don’t stop the truck because that’s the way Steinbrenner did it, every day he was doing something. He would say, if you’ve done one good deed a day, you’ve done God’s work.”

We’ve done book bag drives, Christmas toy drives, and last year, we went to P.S. 55, which is one of the toughest places in the Bronx to live in. Those kids were so happy that Gleyber Torres and others donated to Ray Negron and me, and every kid went home with two gifts. And we want to continue to grow.

Final thoughts from NYC Tastemakers

“Squeegee has a real name, and it’s Luis Castillo.” These were the words I was left with after engaging in an eye-opening conversation with Castillo. Baseball is obviously a huge part of his life, but it isn’t the only thing that matters to him. Luis Castillo is a passionate and strong father of two boys, and he has used all his experiences to guide his life and keep him morally sound.

Since he started in 1998, Castillo has had many exciting stories to tell from his days as a batboy of one of the most iconic franchise in the history of Major League Baseball. Whether it’s warming guys up as a catcher, throwing balls during hitting practice, or taking part in life-changing discussions with his baseball heroes, Luis Castillo has been, and always will be, an instrumental part of the New York Yankees franchise.

Castillo has taken his remarkable eight-year career as a batboy with the Yankees and has built on it, creating a foundation dedicated to providing resources and opportunities for kids in New York who really need it. Through his work at Squeegee Children’s Literacy Foundation, he cares about each individual student, promoting the importance of reading and education, and using his experiences to help them on their journeys. Luis Castillo is a role model in how to use your platform, no matter how big or small, to create meaningful change and make a lasting impact on people.

“Life is going to throw you curveballs, you’ve got to learn how to hit them.” Castillo came up with this clever quote, and it could not ring truer. I was truly moved and inspired hearing his story, being just an ordinary kid who loved baseball, to becoming one of the best batboys in history, to losing his father to cancer in 1999, and having a key role in one of the greatest perfect games in MLB history. Despite being the most famous batboy’s ever, Luis Castillo is one of the humblest people you’ll ever find. I could sense a genuine love and passion for everything that he does with his life, and he certainly made a strong impact on me.

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