Cheshire Academy can boast of being the home of what is almost certainly the most incredible prep school tennis story in U.S. history. It involves two graduates from the class of 1929.
The All-England Club Championships at Wimbledon in 1931 featured the only “walk-over” in the championship match in tournament history. In the second semi-final match, Frank Shields, grandfather of actress Brook Shields, lunged for a volley on match point. He won the point and the match but seriously injured his ankle in doing so. Waiting for him in the final was his former CA roommate, Sidney Wood. Wanting to play Davis Cup for the U.S., along with Sidney Wood, in just a matter of days, Shields forfeited the final match. Wood, however, refused to accept the champion’s trophy, stating that Shields was the better player and would have been heavily favored in the final match. Wood said he would accept the trophy only when he had beaten Shields on a grass court in a meaningful match. That moment arrived three years later at Queen’s Club, still a June lead-up tournament to the Wimbledon Championships, when Wood won a 6-4, 6-4 championship match. The CA roommates would go on to play #1 and #2 Davis Cup singles for the U.S. team for five years. Shields was an unseeded winner at the U.S. Open in 1932. Much later he would serve briefly as a CA trustee in the early 1950s.
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Sidney Wood founded a successful business in New York City after his professional tennis life ended, but he continued to play USTA events. While playing a composite age father/son tournament, Sidney and his 14-year-old son were across the net from Karl Kamrath ’54 and his college-age son. Karl was Texas state champion in every age group beginning at age 14 all the way forward into his 70s. He played at UT Austin on some powerhouse teams. Predictably, the Kamraths prevailed in the match, but, of course, both pairs enjoyed their CA camaraderie.
About 15 years ago, Karl visited CA at age 78 and came out to hit with the boys’ team. I remain astonished to this day by how good he was — and I really “get it,” as I am now 74 and feeling my years as I continue to play competitive tennis. At our team practice, Karl played doubles with our #6 player, and they easily trounced the #4 and #5 players on the team. It was fun to watch, and I know our players will never forget that day.
In 1947 David Markin arrived as a junior at CA and led a strong team as an excellent #1 player. David, as many know, would go on to become one of the most important administrators in USTA history, serving as president of the USTA for two years in 1988-99, He supervised the major reconstruction of the USTA National Tennis Center in New York, a
project that took six years, and served as the Chairman of the US Davis Cup Committee for forty years. His son Justin was a strong player here from 1995-97. Both men have made critical financial contributions to our tennis program.
In 1967, a young man named Lendward Simpson, looking for a strong overall athletics program, came to CA. At that time Lenny was the youngest male player ever to play in the main draw of the US Open – at age 16 – a record broken many years later by Michael Chang. In addition to being a professional tennis player, Lenny was a prep school All-American in two other sports- soccer and basketball. Readers of 1794 Magazine hopefully read my account of a March 2024 trip to North Carolina and the home of Lenny’s nonprofit tennis/education program, One Love Tennis. Two girls and three boys traveled with me. I know they will remember the trip for the rest of their lives. It was certainly about tennis – but much more than that, too.
This tennis history of CA slowly unfolded for me after my arrival in the fall of 1988. I had one year of tennis coaching experience, which was enough for me to know I wanted to do more of it. But there was a problem. There were six courts in very poor condition; one was unplayable, an embarrassment. Imagine my hope and excitement when I discovered that David Markin, the president of the USTA, was a CA graduate. Maybe he would help.
It took some time, but David eventually responded to a letter I wrote and paid a visit to campus. I have thought often of what he experienced as we walked around a campus that lacked more than half of the infrastructure we have today, a campus with a glaring need for rejuvenation. What is clear now is that he felt a deep love for the school, a place that had supported and challenged him, his alma mater. He was flooded with memories and shared many stories. At the end of his two-hour visit, he wrote us a check for the construction of ten new courts and related infrastructure, thereby initiating a tennis renaissance that would positively influence the lives of many hundreds of CA students and adults and, on another level, the entire school. We were able to compete at a high level in NE, host a summer tennis program, establish a very popular recreational program in the fall, and host major USTA events on campus. An unusual friendship developed between us. David was an internationally important tennis figure; I was a developing high school coach. But when we spoke, we were mostly just two CA guys who loved tennis and wanted the best for the school and our players. He sent us tickets for box seats at the US Open every year, which I shared with players and many other members of the CA community, and a yearly check to help with team and family travel expenses on spring break trips to Florida, California and Jamaica. The California trips, only undertaken with very strong teams, involved participation in a National High School Invitational Tournament. I wrote two letters a year to David about the tennis program; his widow Tracy told me he loved those letters and
would read them out loud to her. When David died somewhat unexpectedly at age eighty-three, I was one of the early phone calls from his secretary. Cheshire Academy and its people meant a lot to David, and he surely meant a lot to us. I was honored to be the coach at his school; earning his appreciation and respect is one of the major highlights of my career. I traveled with Head of School Jerry Larson to his remarkable memorial service in Palm Beach, Florida.
To loop back to the beginning, I wrote about all this to illuminate the role of our remarkable history in the present moment and even more so to show how much loyalty and support matter for a school. I have been motivated by the triumphs and challenges of the past. When I spoke at the Markin Courts dedication ceremony in May 1992, I spoke about just this, about following the examples of excellence from the past and pursuing the same greatness of spirit and accomplishment in our own time. I think we have done that, and hundreds of players have been part of it. It has been a joy and a challenge to be the CA coach. But it’s hard to imagine myself saying this, after thirty-six years of striving for excellence, without David’s generosity. CA was a place of joy, striving, and meaning for David throughout his life. He enjoyed giving to the school, and the school gave back to him.
We hope that new generations will follow the example set by David Markin and help us continue to reach our highest potential.
Want to contribute?
Do you have a CA story that illuminates the nature of our great school? If so, please email something in the range of 200-300 words to chip.boyd@cheshireacademy.org.
