A month after celebrating his 50th wedding anniversary, Bob Sides took part in Race Week, Marblehead’s annual regatta, as he had every year for decades.
He had missed only one race, in 1940, because it conflicted with his honeymoon. Fifty years later, he and Kate, his wife and co-skipper, were still racing their boat together.
“Our chances of winning probably aren’t that good,” he told the Globe in July 1990. “These young fellas are tough.” He added that he had forgotten most lessons learned in more than half a century of competing except “patience . . . more patience . . . and never give up.”
Mr. Sides, who for many years was director of admissions at Phillips Academy in Andover, died of cardiorespiratory arrest Oct. 21 in Edgewood, a retirement community in North Andover. He was 96 and lived most of his life in Andover and Marblehead.
He was as well respected for his prowess on the water and on the tennis court as he was on the campus of Phillips Academy, where he also taught and coached.
“In the classroom and the admission office and on the tennis court, ocean, and golf course, Bob drew great joy from teaching students how to find the square root, box a compass, trim a jib, ace a serve, choose a school, and, not least, to win and lose gracefully,” said a tribute on the school’s website.
An alumnus of Phillips Academy, Mr. Sides joined the faculty in 1938. In the late 1940s, he spent two years as an assistant dean at Harvard University, but otherwise remained at Phillips Academy his entire career. Through the years, he taught math and celestial navigation and coached sailing, tennis, squash, and golf.
Mr. Sides became director of admissions in 1954 and retired in 1972. The responsibilities, he said, were fulfilling and at times frustrating.
“Why anyone gets involved with admissions work in these hectic days of heavy overapplication, I’ll never know,” he wrote in the 25th anniversary report of his Harvard College class. “In this business you make about five enemies to every friend. Nevertheless, it’s a challenging and fascinating occupation with rarely a dull moment.”
Robert Whittemore Sides was born in Yonkers, N.Y.
He graduated in 1934 from Phillips Academy, and graduated with a bachelor’s degree from Harvard in 1938.
As a teenager, he sailed at the Eastern Point Yacht Club in Gloucester, where he competed against Kate Meredith Boyce. They married in 1940 and had five children. She died in 1992.
Phebe Miner, a longtime friend who, like Mr. Sides and his wife, Kate, raised her family on the Phillips Academy campus, said he was “a perfect gentleman, very kind.”
Each June, she said, the Sides family invited faculty friends to their vacation homes, first in Gloucester and later in Marblehead, between the end of the regular school year and the start of the summer session.
“It was such a treat, and Kate and Bobby were the most wonderful hosts,” Miner said.
Phillips Academy had been an all-boys school, which made growing up on campus an unusual experience for the four Sides daughters.
Kate Flather of Boston, who attended Abbot Academy, the girls’ school that merged with Phillips Academy in 1973, said her father often “tested me to see if his daughter was learning as much math as the boys at Andover.”
She said her father was a “great role model,” who was admired by students and parents for his gentle and compassionate demeanor, as well as for his love of sports.
Flather said she and her sisters “grew up knowing that we could do anything boys could do,” thanks to his encouragement. “That was one of the greatest gifts he gave us.”
Mr. Sides was “always ready to extend to others the warm hand of friendship,” said his friend Nathaniel Nash.
Nash added that Mr. Sides was devoted to his family and was a “familiar face among spectators at all his grandchildren’s games.”
After his wife died, Mr. Sides “took over the grandparenting responsibilities,” Flather said.
“He never missed a birthday or a game,” she said, “and he never forgot a tennis score.”
She and her father were frequent tennis and sailing partners, and Flather said Mr. Sides was “still racing at 82 and still winning tennis tournaments at 93. He was the most honest and true sportsman I knew.”
Mr. Sides “was just a wonderful man to be around,” said his friend Norman Cressy, who makes sails. “Sailing is such a competitive sport, and there are some people who wouldn’t tell you if your coat was on fire. But Bob was a real gentleman, on the race course, and both before and after the races.”
Even when Mr. Sides was in his 70s and 80s, Cressy said, he would arrive at the yacht club with his boat in tow and hoist it into the water without assistance. “He was a real inspiration,” Cressy said.
At 82, Mr. Sides skippered his boat in a championship regatta. The Eastern Yacht Club honored him with a lifetime achievement award.
A birding enthusiast, Mr. Sides served on the board of the Massachusetts Audubon Society. For the 50th anniversary report of his Harvard class, he noted that he had seen more than “3,600 of the world’s 9,000 species. My target is 4,500.”
A memorial service will be held Saturday at 11 a.m. in the Cochran Chapel at Phillips Academy in Andover.
In addition to his daughter Kate, Mr. Sides leaves a son, Robert Jr. of Marblehead; three other daughters, Sophie Cowan of Blue Hill, Maine, Lucie Bourdon of Lyme, N.H., and Natalie Miller of Lincoln; 16 grandchildren; and seven great-grandchildren.
“We were all so lucky,” said Flather. “What he did for all of us, for the students at Andover, it was all amazing. His whole life was amazing and so much fun.”
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