VINTAGE RYE: Squash Racquets, Anyone?   

0:00 Allan Cummings, a summer pro, at The Meadow Club in Southampton in 1937    Champion Bobby Riggs flanked by Allan Cummings and Mr. Anthony at […]

Published January 17, 2021 2:02 PM
5 min read


Allan Cummings, a summer pro, at The Meadow Club in Southampton in 1937 


Champion Bobby Riggs flanked by Allan Cummings and Mr. Anthony at The Meadow Club in 1937. 


Allan Cummings holding the Cummings Cup in 1966. 



Squash RacquetsAnyone?   




Driving down Milton Road, one could easily miss a lovely, tranquil neighborhood known as Sand Park which includes Sand, Ivy, and Fenton streets. It was aptly named in the 30s when the area was just mounds of sand and dirt roads. I played a lot of jump-rope there as a kid while visiting my cousins who lived on Fenton.   


Some of the same families over the generations have lived there and live there to this very day. There were the Whites, the Brennans, the Walshes, and the Cummings to name a few. As children we all played together and truly had little idea what our parents did for a living. That was never an issue; we just had fun enjoying each other.    


As time goes by, it is interesting to realize that two of the three renowned Cummings brothers, Allan and Lester, stayed in that neighborhood. The third brother, George, lived in Darien. George and Allan were born in Aberdeen, Scotland and came to America in 1908Lester was born in the States. Often referred to as the “Cummings’ Dynasty”, they were top-ranked American Professional Squash Racquets players who won a remarkable number of Squash Racquets National and Open tournaments back in the late 1930s and 40s, and on into the 1950s and 60s.  


Thsomewhat exclusive game of squash racquets, more commonly called squash today, arrived as a winter sport after World War I. Its popularity began in the more elite prep schools and colleges of the East Coast, primarily in New York, Boston, and Philadelphia, even though its humble origin may have been in the debtor’s prisons of London. Professional squash racquets players didn’t tour; they stayed close to home, putting on exhibitions at private tennis and golf clubs, often donating the gate receipts to charity. 


The three Cummings brothers competed as partners as well as against each other, becoming legendary. It was the golden age for highranking amateurs to play with or against professionals, all before the commercialization of sports. Remuneration was not the motivator; rather, it was the joy of competing on a high level in a sport they loved.  


Apawamis Club, one of the very first clubs in the East to take up the game of squashwas a frequent host of these exhibitions. In December 1940, four of the topranking squash professionals in the country — the three Cummings brothers and Tom IannicelliNational Professional Squash Racquets Champion and professional at Short Hills Club — played a sensational doubles match there. They charged one dollar to be donated to the British War Relief Society. At the time it was a headlinemaking event. 


The eldest brother, George, began his court career in 1919 as head tennis and squash professional at the University Club in New York City, teaching squash in the winter and tennis in the summer.  It was George that inspired his younger brothers, Allan and Lester, teaching them and training them to be expertsGeorgeconsidered the mastermind of the game’s strategy, was twice National Professionals Open doubles champion and Allan and Lester were threetime finalists. Each is legendary in his own right; each became a professional.   


In 1932, Allan began his professional career at the Union League Club in New York City. During the summer he was also the Racquets Professional at The Meadow Club in Southampton. Over the years he was associated with numerous area clubs including: Manursing Island Club, Belle Haven Club, and The Field Club of Greenwich. Starting in 1940, he spent 34 years at Apawamis Club and went on to become a tennis, paddle, and squash professional legend. 


Lester, the youngest of the three, spent 31 years at The Field Club of Greenwichstarting in 1943He regularly invited pros to practice at the Club before their championship title matches at Forest Hills, and members flocked to the club to watch and be inspired. 

He was a four-time winner of the North American Pro title during the late 1930s and early 1940s.  


Peter Briggs, himself a National and Open champion many times over, and Apawamis Club’s longtime Racquets Professional considers Lester Cummings, who coached him as a boy, to be one of his most important mentors. He affectionately referred to Lester and his brothers as the real deal”, downtoearth gentlemen who excelled at their sport. 


Allan was considered the “most severe hitter”, creating many an opening through which Lester executed brilliant winners. Allan enjoyed playing on the right side of the court neatly finessing superb drop shots, and would mix it up, by hitting with great power on other occasionsHe was also renowned for his “nick shot” where the ball was hit to the corners of the court at the intersection of the floor and sidewall, causing the ball to roll parallel to the floor, losing momentum, making it virtually unreturnable. 


The galleries were always highly amused by the keen rivalry of the Cummings brothers who never gave an inch on the court, especially in their younger days. The brothers hit stinging blows and were often appealing to the referee for “lets”, called when a player obstructed an opponents playThe Cummings had the ability to be competitive on the court and afterwards fraternized on funloving brotherly terms, a credit to their fine sportsmanship and their Scottish mother who tutored them: “I donna care who wins…as long as they play fair.” 



During Allan’s time at The Meadow ClubBobby Riggs would play in lawn tennis tournaments there. Today, Riggs is more famous for being defeated by Billie Jean King, in a muchpublicized 1973 tennis match. But Riggs was a topranked tennis player in the 1930s into the early 40s, considered a bit of a hustler and often “full of himself” by the reserved tennis crowd. Taking stock of the tennis doubles roster for a tournament at the club, Allan famously and coyly asked“I wonder, we’ve got 29 teams already. Have we missed anybody?” When someone softly pointed out he had failed to include Bobby Riggs and his partner, Edward Cooke, Allan, without hesitation, responded“Oh well, with all the confusion around here, how can a guy remember trivial teams like the Wimbledon Champions?” which he quickly corrected with the flourish of a pencil. 


Professionals and students taught by the Cummings brothers, still express overwhelming gratituderecalling how the brothers were always accessible, helping aspiring young pros “chomping at the bit” to improve their skills and sharing stories of their early career.   


Apawamis member J. Ellis Knowles, a five-time U.S. Senior Open Golf champion, 

summed up the impact of Allan Cumming’s career upon his retirement in 1974“Allan taught so many…how to win humbly and lose with honor.” Those profound words can be said about Lester and George, as well.   


The Cummings Cup, a friendly singles/doubles tournament between amateur members of Apawamis, the Field Club, Greenwich Country Club, and Round Hill, was created in the early 1950s to honor these three siblings, all of whom headed up club programs until they were well into their 60s.   


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