Will Castro riding his bike
We also went to work early. There’s a famous Broadway play called Newsies, and me and Kenny were newsies like that, just 1970s versions. We sold the New York Post, and we said one thing, on repeat: “Get your Post here! Get your Post here!” You had to be aggressive just to make a couple of dollars, but it started one thing in me very young: reading the newspaper. The news of course, but especially the sports section. The back page had the standings, and I started learning about averages and winning percentages and how the Yankees were doing. You know, what’s a “clincher,” when you clinch the title or when you clinch the division. The Yankees were a big part of our New York culture there. Selling newspapers also showed me the joys of making money and having some bills in your pocket.
“Selling newspapers also showed me the joys of making money and having some bills in your pocket.”
This was also a period in time when cars were becoming very important to me, and Kenny had a huge influence on me in that regard. I think if it wasn’t for him, I would not have been into cars. That’s the truth. It began when we were kids, playing with AFX cars, lying down the track and racing. Later on when we got older, Kenny was the first one of us to get a car: a Plymouth Satellite Sebring. I was in love with that car. Kenny brought me around to his uncle’s garage, where he used to park cars, and then I became a valet parker at Mario’s Restaurant. I just did a lot of the things that Kenny used to do. I used to definitely look up to him, like he was a bigger brother, but he was only maybe a year older than me. But this era was later. Once again, I’m getting ahead of the story.
When I turned about fourteen years old, my mother decided to move us to Brentwood, Long Island. She felt New York City was changing, so she wanted to get out of the projects and wanted me and my little brother Bobby (seven years younger) to have some space and get into better schools. This was the early 1980s, and things were changing in the city; money was getting more prominent. The rich were taking over. Brentwood is a working-class town in the middle of the island, not far from Islip. Today, there’s a big Hispanic community there and lots of African Americans too, also whites. It was a rough transition for me to move, and it took me a couple years to fully adjust. First of all, the kids in school fought a lot; the races did not get along. I was perplexed by this. There was no racism in the projects of the LES. Everybody was a minority. But, in Brentwood, we’re supposed to be going to a good school in a good neighborhood, yet it turned out that Brentwood was crazier than New York. The famous TV mini-series, Roots was out on television at the time, so young teenagers’ sense of racial identity was heightened by that. That show emerged at a time when the whole country shared the same television culture, and it had a huge impact. I said to my mom, “You got to be kidding me, Mom. You told me that this was going to be a cool environment!” There was truly a divide, and I wasn’t about that. For the first time in my life, I really woke to the differences in race and class in New York.
Eventually, one adjusts to a new school with new attitudes, and the way you do so is by earning your stripes. You stand up to racism by not tolerating it. “Around me,” I said, “don’t do that. You don’t treat anyone any differently.” And I had to tell people that. I wouldn’t tolerate the N-word being used or anything else of a derogatory nature, because that’s not what we’re about on the Lower East Side. It never was about that.
“For the first time in my life, I really woke to the difference in race and class.”
I had to get adjusted and that took a long time. Years, in fact. My friends had to come see me from the city. They met my mom at the Gouverneur Hospital where she worked, and they would drive out with her to Long Island every Friday. They made the transition a little easier for me. I didn’t want to live there. I just didn’t, because, you know, living in the city was totally different from living in the suburbs. It really was.
Down in the LES, you could come out of a building, and you’d see a thousand people living in one house. You could see your friends downstairs. We had so many parks you could walk to, bike to. On Long Island, you had to have a car to get anywhere.
I also had the added burden of being a city kid, an outsider not native to the island. That played both ways, because the suburban kids looked to guys like me for their sense of style. We had the flyest kicks, bomber jackets, baseball hats, and fly jeans. We were from the city, and our swagger was different that way. I had the fly wares. I had a burgundy sheepskin with a crown with the 69ers to match. I had suede Pumas. As the fashions came out, that was what it was in the city. It was all about that, because you had to have status if you’re coming out of your building. You had to have the right kicks. You had to have the right jeans. You had to have the right bomber. If the goose down was out, you had to have that. And my grandfather made sure I had everything I pretty much wanted. I brought this sense of fashion to Long Island. I also brought music. It was me and kids like me who had the Grandmaster Flash tapes, the Busy Bee tapes. And the suburban kids wanted all that stuff.
Will plays Bruce Lee, circa 1970
I began playing sports as a young kid in the LES; I took karate with Kenny, little league, things like that. And so when I hit Brentwood, I continued to play football and baseball. This kept my mind off the transition and the fact that Long Island really didn’t feel like home at first. That was good. What was bad was that my mom still worked in the city, so I felt badly about her commute and how hard she had to work. She knew this. My mom had to work, while a lot of other parents, including many stay-at-home moms, would drop off their kids at practice and go to games. My mom couldn’t do that. My dad couldn’t do that. My grandfather couldn’t do that. So I didn’t have that support. My parents were working. They couldn’t come to games. Later on in life when I had my first child, Paige, I tried to do things differently. I went to her track meets and cheerleading competitions. But I understood my mother’s position. I understood she had to work.
I would get on her sometimes, saying things like, “Oh, you know, Tippy’s mom was at practice.”
My mother said, “Lemme break it down to you. I work.”
In high school when I was fifteen, I met Marilyn, the woman who would become my first wife and the mother of my first child, Paige. Marilyn showed me what Suburban life was. If it was not for our relationship, I may not have gotten into the car business the way that I did. We met at Bay Shore Roller Rink. Most of us were still too young to drive, so all the parents would drop us off there. Now, for some of you young people reading this, you may not know what a roller rink is, but, in the seventies and eighties, these were places of great entertainment for teenagers. We’re talking roller skates, not ice skates. The lights on the roller floor would be low and theatrical, like a disco or a dance club. Instead of asking a girl to dance, you’d ask her to skate, if the right song was on. Then you’d hold her hand and spin around and around the roller rink. There was a snack bar with bad pizza and an arcade with pinball machines, Asteroids, and Pac-Man. Disco and early rap were blaring over the sound system. Sugar Hill Gang, Bee Gees, Kool and the Gang. Rock too. Led Zeppelin and The Who. Pink Floyd. “We don’t need no education.” Teenage hormone heaven. Bay Shore is gone now, long ago ripped apart by a wrecking ball. But back then, it was the center of our teenage social life. Every Friday night, we’d head over there in our school football jerseys, showing team spirit for the game the following day. Wearing your jersey was a way to rep your town: Brentwood, Bay Shore, Islip. One night I was at the roller rink with Kenny Williams, and he skated up to Marilyn and her friends.