In Memory of





Obituary for William F May Jr.

MAY, William F. Jr. A Life Well Lived Died at home in Winchester on Sunday, August 9th with family all around after he fell ill early this year. He was 88. Born in Waltham, and raised in Wellesley Hills, he was the youngest of six children. He was predeceased by his father and namesake, William F. May, Sr., his mother, Mary Tulis May, and his siblings Virginia May Mansfield, Gloria May Sessions, Marylou May Hartmann, Suzie May Haag, and brother David. His wife of 62 years, Ann McCauley May, survives at home, as well as his children Sarah May (Kris) Clarkson, Timothy T. (Carolyn), Peter M. (Sandy), Alexander T. (Sheila), and Julie May (John) Daniels. His nine grandchildren are Joseph R. and William R. Clarkson; Natalie T. and Aidan M. May; Jacob A. and Elizabeth J. May; and Sarah D., Benjamin M., and J. Annie Daniels. Also surviving are numerous nieces and nephews. A Chartered Life Underwriter (CLU) and Chartered Financial Consultant (CFC), Bill May sold insurance as an independent broker for more than five decades, continuing to work until just last year. He was valued and appreciated by clients and business employees for the care and concern he showed for all parties. He considered his work deeply interpersonal and was a gentleman from beginning to end. He was a multi-talented athlete, scholar, and polymath. A graduate of the former Cranwell Prep School in western Massachusetts, he went from there to Boston College for one year, but transferred to Hamilton College in Clinton, New York, to play inter-collegiate hockey. At Hamilton, he also played baseball, but hockey was his favorite team sport. An English major in college, Bill was an inveterate reader of fiction and non-fiction, and could -- so many years later -- still recite the Latin and Greek verses he was required to memorize during his college studies. He was an artist, photographer, and student of Italian language and culture. After college graduation in 1953, he enlisted in the Army and served for two years in Erlangen, Germany, as part of America's cold war force in eastern Europe. He was honorably discharged in 1955. He met Ann McCauley skiing at Cannon Mountain in New Hampshire during the winter of 1957 / 1958, proposed to her in February and married her two months later, 12 April 1958. They lived in Walpole for five years, then moved to Winchester in 1965, and have lived in the same house ever since. Bill May was a fan of all sports. He played football, hockey, and baseball in his younger days; he was a strong and graceful skier, he fished, and he thoroughly enjoyed the game of golf in his last two decades. When he wasn't playing golf, he was watching every imaginable sport on the television -- soccer, rugby, college contests, and all of Boston's professional teams. He could recall taking the trolley as a boy from Wellesley to Fenway, getting a bleacher seat, enjoying a hot dog and a drink, and then taking the trolley home -- for about $1.10 total. The family especially wants to thank Ivan Ssebowa, David Kirabira, and all the staff at Right at Home; we will be forever grateful. A funeral mass will be offered at St. Mary's Catholic Church, 155 Washington Street, Winchester (where he and Ann McCauley were married), on Friday, August 14th at 10 a.m. The family will be glad to have friends gather with us, but we ask that health and safety protocols be followed in the church. The ushers will help seat everyone carefully. A short graveside service will follow the mass. In lieu of flowers, please consider making donations in Bill May's memory to the public library of your choice, to the Catholic Church's social welfare charities offering assistance directly to the people (such as St. Vincent de Paul), the Pine Street Inn, or to any social justice non-profit of your choice. In a very recent conversation when asked what his epitaph would be, Bill May did not hesitate: Treat others the way you would want to be treated. He was our north star, our touchstone, our rock -- a more kind and patient and generous man never lived. We are lost without him, but will use his epitaph to guide us going forward.