Richard R. Stewart '49 was a longtime squash player and winner of three national amateur singles championships before he joined Frank Millet to coach the Milton boys' squash team. Scotty, as he was known at Milton, died suddenly June 22, 2005 at his home in Ipswich. There was an informal gathering in the Williams Squash Courts on Friday, December 23, 2005, for Scotty’s family, classmates, players, their parents and friends. Hayden Jacques, captain of the 2000-2001 team, spoke movingly for the many members of Scotty’s teams who were present. During the five years that Scotty coached the 1st Team, the record was 58 wins and 8 losses. 

In Scotty’s memory, in recognition and admiration for his coaching, the Scotty Stewart Award for the Most Improved Player will be awarded annually to the player who, in the coaches’ opinion, has improved the most. The first award was made in 2006 for the 2005–2006 season and the first recipient was William C. Sullivan '09. 

Scotty is missed by Milton’s squash community. His powerfully calm, very personal instruction, always punctuated by light humor, guided each player, no matter what his ability was, to reach his potential.

 One of his younger players wrote when he learned of Scotty’s death; “I was deeply saddened to hear about the passing of our lively friend Scotty. He was always very upbeat and enjoyable to be around, on and off the court. He helped the squash team tremendously and will be a hard loss for all the boys, but his critiques and comments will be remembered and cherished by all the members of the squash team. I will always remember the many good times we had with our coach and mostly our friend.”

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