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Tennis with a legend

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ATHLETICS

ATHLETICS

Five CA students spent their spring recess learning about tennis from one of the sport’s greats.

By Chip Boyd P’10

I first met Lenny Simpson ’68 at Cheshire Academy’s bicentennial celebration, held on campus in 1994.

The bicentennial was an important event in our school history, and it drew a large crowd for festivities under a huge tent. When I walked in, knowing Lenny was there somewhere, I saw a large cluster of people off in the corner. For reasons you will readily understand as you read ahead, they were clustered around Lenny, most of them teammates from one of three sports he played at CA. Incredibly, he was named a prep school All-American in all three — soccer, basketball, and tennis — in 1968. Lenny’s warmth and charisma were evident from the start, and I have enjoyed a friendship with him ever since.

Some of my contact with Lenny was during his tenure as a member of the CA Board of Trustees from 2010-2015. He was on campus more often during those years, including one visit when a filmmaker from the International Tennis Hall of Fame (Newport, Rhode Island) was here to interview him before his induction, and another time when he was here as the keynote speaker for our Martin Luther King Jr. Day programming, when he presented his highly celebrated documentary film on legendary tennis player Althea Gibson. Our students engaged deeply in his excellent presentation; many of them were amazed to learn that Gibson was the first professional athlete to “break the color barrier” in not one but two sports: tennis and golf. Many were duly surprised that they had never heard of her. I will leave it to the reader to consider why this was so. I expect there will be a few readers of this article who were present for Lenny’s presentation.

I have traveled with CA tennis players to many places around the United States during my 35 years of coaching. I had long contemplated a visit to Wilmington, North Carolina, where we could link up with Lenny on his home turf, and this was the year to do it. So, I was excited on March 19, when five student-athletes traveled with me during this year’s spring training recess to Wilmington. We were there for a week and had a memorable and stimulating experience that included demanding tennis, vivid social experiences, and lots of education about American social and athletic history. One particularly vivid moment was during our tour of the education center at 1406 Orange Street — Lenny’s residence with significant historical meaning for the world of tennis and Wilmington area — when Lenny showed us the “hiding place,” a small door in the wall through which children would go to hide when the Ku Klux Klan was just outside “protesting” the education and civil rights activism going on inside.

For our team’s stay in Wilmington, some of us stayed at the Ritz; others stayed with Lenny and his wife of 50 years, JoAnn, in their beautifully restored home, which is now a recognized historical site in Wilmington. The house, which you see in the photo at left, was once owned by Dr. Hubert Eaton, a top-level tennis player, a practicing physician, and a courageous civil rights activist. In the backyard there was — and still is — one soft-surface tennis court, one of the important places where Lenny and many fellow Black players trained many years ago. One of those players was Gibson. She lived with Dr. Eaton and his wife for 10 years as she trained to become a world class player. Once in extreme disrepair, 1406 Orange Street is also the home of One Love, Lenny’s nonprofit that serves many Wilmington children of all kinds through expert tennis training and one-on-one academic enrichment experiences.

One particularly vivid moment was during our tour of the education center at 1406 Orange Street — Lenny’s residence with significant historical meaning for the world of tennis and Wilmington area — when Lenny showed us the “hiding place,” a small door in the wall through which children would go to hide when the Ku Klux Klan was just outside “protesting” the education and civil rights activism going on inside.

Lenny was once ranked as high as 37th in the world and has been an important person in U.S. tennis ever since. As great as this is, there are other facts of his early athletic life that are also remarkable. When he moved from The Hill School (Pennsylvania) to Cheshire Academy to engage in a higher-level athletic program in September 1967, he had just recently been the youngest participant ever in the U.S. Open, competing under 16 years of age. Lenny’s CA soccer coach, a native of Germany, tried to persuade Lenny’s mother to allow him to spend the summer with him in Germany to pursue a career as a professional goalkeeper. Lenny’s mom said “no.” When he went to college, Lenny attempted to play both tennis and basketball at the Division I level, but soon found handling tennis alone was demanding enough.

I could go on about this impressive CA alumnus. You can visit his website (one-love-tennis.org) and you can purchase a recently published book about him on Amazon: “In the Shadows of Tennis Legends: The Lenny Simpson Story.”

What follows are some brief testimonies from the five students who traveled with me. I told each of them they represented their families and our school beautifully. I know that Lenny, a proud CA alumnus, was proud of all of them too, both on and off the court.

ANJALI GURURAJ ’23

Visiting the Simpson family in Wilmington was an incomparable experience. In the week we spent with them, I learned more about myself as a tennis player than I imagined possible. Mr. Simpson taught us how to effectively use court space in doubles matches, a very crucial part of the sport which I am now incorporating into my game.

We trained with local high school kids in the mornings and afternoons, and then spent the evenings hearing about Mr. Simpson’s amazing experiences playing in the U.S. Open and Wimbledon. He shared stories about Althea Gibson and Arthur Ashe, his personal friends and two of the greatest tennis players of their time who broke the color barrier and changed the face of the game. Mr. Simpson’s love for the sport can be seen in his passion for helping young developing players acquire skills that will take them to the next level.

This trip taught me a great deal about the struggles people of color lived through in the past to ensure that in the future other young players of color just like me are seen as equals every time we step out on the court.

ANNA BLOOM ’24

My experience working with Mr. Simpson and the One Love Tennis Foundation was both an enjoyable and educational experience. Not only did we get some one-on-one time with Mr. Simpson himself to improve our gameplay, we also got the chance to help coach young kids who are new to tennis, and to see them improve. Watching Mr. Simpson coach taught me a lot about what it means to be a leader. He is deeply respected in his community. You can see that from how kids, including myself, look up to him.

DAVID CARROLL ’24

While visiting the Simpson family in Wilmington, we were fortunate enough to meet and play against many great tennis players our age who attend North Carolina high schools. We also had a chance to coach students much younger than us. Everyone had a blast. I saw how Mr. Simpson was an inspiration to not only the little kids playing tennis but to all the kids in the area. When the kids first stepped onto the tennis court, they ran to and hugged Mr. Simpson. He was strict and fierce in a good way when he was coaching us on the court, but right when the little kids came, he showed his true self — he is a big teddy bear who cares about everyone.

Even though it wasn’t intentional, he taught me that I must truly know someone before I can understand what type of person they are. The first day that we arrived in North Carolina, Mr. Simpson came off as a sort of grumpy person who wants to live his way. I thought this was how the entire week was going to go. When we started to play tennis, he sat in his chair, loudly urging us to play with more awareness, focus, and intelligence.

It only took a few days to find out that Mr. Simpson was an amazing person whose only goal this week was to give us a great time and help us become better tennis players. He taught us the value of listening in practice, how to play doubles correctly, and how to get more consistent in hitting ground strokes.

On the last day, Mr. Simpson came to us and gave us a heartwarming speech. He talked to us about the many misfortunes that have happened to him in the past few years, saying that he should be dead right now. He said that, in the past three years, he has had three strokes and is battling cancer. All the doctors said that it is a miracle that he is still alive. He said to us that he never knew why God decided to keep him alive all this time, but he felt sure part of the reason was to meet us and share his amazing story with us. Mr. Simpson then started to tear up while saying how great of a group of kids we are and that he was truly blessed that he got to meet us.

JACK SILANO ’24

My experience with Mr. Simpson and the One Love Tennis Foundation is one I will not soon forget. While I have only been playing tennis for a short time, there are a few names anyone who has played the sport should know, names such as such as Arthur Ashe and Althea Gibson, who were Mr. Simpson’s friends and mentors. To play on the very court where both of those legends trained and to be in the house where they lived — where the Simpson family now lives — was a new way for me to experience American history. To be coached by Lenny Simpson, a man who grew up to be a world-class tennis player after learning from those legends, was just as surreal. I was able to learn techniques and strategies and ways of playing the game I had never even considered or heard of. It is true that professionals like Mr. Simpson have a vast wisdom of the game, I am forever grateful that he was so willing to share all of it with us.

DANNY XUE ’24

It was a great experience to travel with Mr. Boyd and my classmates to Wilmington to meet Mr. Simpson, a tennis legend, and to learn a lot about the sport. Mr. Simpson has many players who have followed him from a young age, who he let us play tennis against and learn from. Some of them played very well; they all had different backgrounds, and it was great to meet all of them. I also participated in volunteer activities to teach young kids who are part of One Love tennis. I feel that this volunteer activity was very meaningful for me because it was the first time I was able to serve as an assistant on the court. I also learned some stories about One Love Tennis and Mr. Simpson’s personal experiences as well.

As you have read, the students and I had a wonderful experience in Wilmington. It was a deep pleasure for me to watch a once-world class player with 30 professional doubles titles to his credit coach our players in doubles technique. Lenny and JoAnn made us feel at home and frequently expressed their pleasure in having us there. It is an honor for me and our players to consider Lenny and JoAnn our personal friends.

If you ever travel to Wilmington, be sure to stop in to say hello at 1406 Orange Street. I know for sure that Lenny and JoAnn will welcome you with open arms.

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