Excerpt from A History of Squash at Deerfield Academy

The following 2008-09 season Charlotte Dewey was joined by her twin sister Hallie and cousins Tori and Katie, and this trio along with Kempner, Havens, Seldy Gray and Kathryn Grace “K.G.” Kaelin weathered a rough start caused by injury (Charlotte Dewey severely sprained her right ankle in a soccer game against Northfield Mount Hermon and was sidelined until January) and illness. The four Deweys and their teammates finished the season with a strong second-place showing behind Greenwich Academy in the New England Interscholastics by earning one point more than Taft. As had happened 14 years earlier in the 1995 edition of this tournament, there was a 20-minute period while the scores were being toted up, and this time no one had figured out beforehand what the outcome would be (as Coach Schwitter had done back then), so when the announcement was made that Deerfield had edged out Taft for second place, the Green and White girls cheered loudly and giddily noted in the van ride home that they therefore came in first among New England boarding schools.

   In an incredible case of bad luck, on the Saturday exactly 52 weeks after her ankle sprain, Charlotte Dewey tore the anterior cruciate ligament in her left knee on the same Northfield Mount Hermon soccer field in October 2009 and was forced to miss the entire 2009-10 squash season. In her absence, a Deerfield lineup consisting of Hallie Dewey, Nina Kempner (who courageously played the entire New England Interscholastic weekend despite a bad case of bronchitis), Seldy Gray, Emily Jones, Tori Dewey, Caroline Kjorlien and captain Lilly Havens all placed either second or third in their respective brackets, contributing to a third consecutive top-three finish in that event.

  But throughout that time even the success that Coach Heise’s troops were experiencing was shadowed by the growing frustration of never being able to break through against their nemesis Greenwich Academy, whose players took the New England Interscholastic trophy back to their school on North Maple Avenue for the 14th consecutive time in February 2010, enabling their excellent coach throughout that period, Karen Schmidt-Fellner, a two-time late-1970’s Exeter captain and then the No. 1 at Wesleyan, to end her tenure in a blaze of glory. Even the few times that Deerfield had managed to defeat the Gators in the annual dual meet, the Green and White had never been able to consolidate this achievement in the flagship event for supremacy in New England girls squash. By the time the 2010-11 season began, the Dewey twins, who occupied the top two positions, were seniors; their time to defeat GA when it truly counted was now or never, as was also true of Nina Kempner, Seldy Gray and Katie Dewey. Being “the best boarding school” was no longer a satisfying or acceptable consolation prize. This quintet of seniors and their teammates Emily Jones, Tori Dewey, Addie Fulton and Hunter Sechrest, therefore fully recognized the urgency of that season, which they entered with a burning determination to finally capture the crown that had eluded them for so long.


   Throughout that 2010-11 year, the top two schools, both in New England and in the nation as a whole, were Greenwich Academy and Deerfield, and between them they so thoroughly dominated the competitive landscape all winter that it is fair to say that that entire year revolved around the three times that the two teams met. Deerfield went 17-1 in dual-meet play, the one loss being in early December by a 4-3 tally to GA, which got wins at No. 1 from Nina Scott over Hallie Dewey, as well as at the Nos. 4-6 positions (Skylar Murphy over Kempner, Jocelyn Lehman over Gray and Lindsey Scott over Tori Dewey), while Deerfield’s points came from Charlotte Dewey, Jones and Fulton. Lehman’s win over Gray was 11-9 in the fifth, and each of the seven matches had at least one two-point game. Actually there were 10 matches played that day, with Deerfield sweeping the No. 8-10 matches, but only the top seven matches counted in the final team score.

  The two teams battled each other again a few months later in late February at Yale University’s impressive Brady Squash Center in the final round of the U. S. High School National Squash Championships, a competition that had been established by the USSRA (which had renamed itself U. S. Squash) in 2005. The match was much more closely contested than the 6-1 score --- all four games in Charlotte Dewey’s loss to Nina Scott were decided by two points, and all seven matches either went to a fourth game or had at least one game that ended in a tiebreaker --- but it marked the fourth consecutive time (and sixth overall in the seven-year history of the tournament) that the Gators, now playing for first-year coach Suzie Pierrepont, who had been ranked in the top 30 of the WISPA pro women’s tour only a few years earlier, exited New Haven in possession of the silver cup-shaped winner’s trophy. The headline of the write-up in the local Greenwich newspaper sounded almost bored with its declaration “Dream Realized, Again.” The opening paragraph read, “Winning a national championship is an accomplishment most athletes can only dream of. Yet the dynasty known as the Greenwich Academy squash team lives the dream every year.”

   Yet even the quotes of the GA players sounded more relieved than exultant and seemed to reveal an understanding of how formidable a rival Deerfield had become. Anna Harrison, who lost the only match of the day to Hallie Dewey at No. 1, admitted, “We were a little nervous playing Deerfield because the last time we played them it was 4-3,” while her teammate Isabelle Dowling (later a co-captain of Harvard’s national championship 2015-16 team, just as her parents Joe Dowling and Diana Edge had been captains of their respective Crimson championship teams in 1986-87) noted, “Even though it was 6-1, all the matches were real close and could have gone either way, so it was exciting.”

   What was even more exciting was what happened on February 27th, when the final rounds of the 2011 New England Interscholastic Division A Championships were played. For the first time in the history of the tournament (which by then had grown to a seven-tier format), the 14 finalists were all from the same two schools, with each final pitting a GA player against a Deerfield opponent, effectively turning the Interscholastic team final into a premium-priced dual meet, this one for all the marbles. It was hosted by Deerfield Academy and its stunning Dewey Squash Center, which was overrun all day by students, faculty, team family members and supporters exhorting the Green and White and hoping for the first Deerfield team Interscholastic squash title since Fiederovicz and her crew had triumphed back in 1995.

   Playing on their home courts certainly helped the Deerfield girls that day, as did the absence of Harrison (injured back) and Lehman (compartment syndrome in her left leg), along with the GA default at No. 4 when Lindsey Scott was accidentally hit in the face by Emily Jones on a racquet follow-through late in the first game and could not continue. Those factors aside, that afternoon and evening exacted every ounce of physical, mental and psychic energy that Deerfield could muster from its players, coaches and spectators, who packed the arena all the way back to the windows, clapping loudly and then watching breathlessly as the epic struggle forged onward to an excruciatingly close culmination.

  In addition to the default point at No. 4, Deerfield got wins from top seeds Tori Dewey and Sechrest at Nos. 5 and 7, while Dowling at No. 3 and Sarah Haig at No. 6 defeated Fulton and Kempner respectively, and at No. 2 Alexandra Lunt edged Charlotte Dewey by the narrowest of margins, 11-9 15-13 4-11 14-12. This left both the New England Interscholastic individual championship and the New England Interscholastic team championship to the last match on court, the No. 1 match between Hallie Dewey and Nina Scott, who had defeated Dewey three-straight (albeit 11-9 11-9 12-10) in the dual meet 12 weeks earlier and had won her three pre-final matches without dropping a game.

  Scott won a close first game 11-8, lost an even closer second, 11-9, and won an even closer third 15-13, the overtime points of which were long and enervating, leaving Scott ahead on the scoreboard but gasping for breath throughout the between-games break. Noticing this, and believing that well-placed front-court shots would therefore tire her opponent even further, Dewey successfully pulled off several precise drop shots which caught Scott flat-footed and fell for clear winners at the outset of the fourth game. This gave Dewey the confidence to continue this tactic, even a few times when she was behind Scott in the court, and her hot streak continued to 8-0, at which stage Scott decided to let the rest of that 11-0 game go in order to conserve her energy for the fifth. By this time, all of the other matches were long over, and everyone was crowded around their court, including the players from the other schools, many of whom were hoping that Greenwich Academy, the behemoth of prep-school squash for so long, would finally be dethroned, even though they themselves had no personal stake in the outcome.

    The climactic final game seesawed tortuously through regulation and into a prolonged overtime session, with each player earning match-ball opportunities multiple times, only to have her opponent in each case even the score. Hallie Dewey later acknowledged that several times, as she caught her breath after a gut-wrenching exchange, she felt on the verge of collapse, only to be revitalized by the sight on the other side of the glass back wall of the imploring yet supportive faces of so many friends and family members (including Grandpa and Grandma Dewey, both in the gallery just a few rows back of the front), all of them heartily cheering her on. By the time the tally had reached a hair-raising 16-all, a total of seven match-balls (four for Scott and three for Dewey) had been fended off, the points were getting longer and longer and the darkness of the New England winter night had enshrouded the entire campus, imposing on the crammed squash arena the kind of riveting and dislocating force that mad dreams sometimes exert upon a just-awakened sleeper.

   In the end, this captivating struggle turned into a dream result for Deerfield as Hallie Dewey responded to the mind-bending exigencies of the moment by wrong-footing Scott, who was leaning for a cross-court, and instead lashing a winning backhand drive down the near wall. A lengthy all-court exchange then ensued that ended when a slightly off-balance Scott attempted a forehand drive from mid-court that bounced right back at her for an obvious match-ending stroke call that gave the Green and White girls squash team its first New England Interscholastic team title in 16 years and clinched what may have been, given the magnitude of the circumstances, the opponent and the historical backdrop, the greatest team achievement in the history of Deerfield athletics. The for-once-vanquished Greenwich Academy players swiftly and in some cases tearfully exited the arena, determined to come back better than ever the following year (as indeed they did). By contrast, the exhausted but exultant Deerfield players and their delirious though emotionally drained supporters raced onto the court to mob Hallie Dewey and then celebrated court-side for nearly an hour, with cameras clicking throughout to frame and preserve the moment.

   Hallie Dewey was one of six people cited in the “Faces In The Crowd” section of the March 14th edition of Sports Illustrated, and she and her sister Charlotte were named co-winners of the Bayne Bowl. They then were co-captains of Deerfield’s lacrosse team (Charlotte had also been co-captain of the soccer team) and were its two leading scorers (Hallie tallying 40 goals and Charlotte 30), culminating that season, appropriately enough, with a 14-13 double overtime victory over Greenwich Academy that ended when Hallie, no stranger to triumphant overtime endings against GA, registered the winning goal. She then lettered all four years on Princeton’s strong teams, playing as high as No. 6 and earning praise from legendary Tiger coach Gail Ramsay for her “positive personality, dedication, hard work and leadership that made her an outstanding role model for her teammates.”