Henry M. Jaffe (Miles), 82, of Chilmark, died Feb. 15 at his home on Stonewall Road, with his wife and family around him, as he had wished. He had lived an energetic, athletic, intellectually lively life for most of his years, surrendering unwillingly to vascular dementia at the end.
He was well-educated; Choate School, Harvard College, Yale Law School. A master’s degree in economics from Yale kept him out of the war in Vietnam. Of all his fine schools, he considered Shady Hill in Cambridge the best.
He effectively wrote his own obituary for the Shady Hill alumni bulletin, class of ’55, saying “I was a lawyer working at a Wall Street firm, got bored, then my own small firm, did some civil rights work representing the Mississippi Freedom Democrat Party, but then dropped out, wrote a guide to American ski resorts*, then got involved with European and New Zealand real estate and finally had a depression from which I have never recovered.” (*Skiing The Best, Random House, 1983, co-author Dennis Krieger.)
Miles was a lawyer, a magazine publisher, a real estate investor. For people around him, he was a useful pre-Google reference source for European history and current American politics. He was a generous contributor of both money and his time to all Democratic Party presidential candidates since he advanced for George McGovern in 1972. He died not knowing if Trump would be indicted and sentenced, but sincerely hoped so.
Miles was a gifted athlete and sportsman. He risked his friends’ lives (and his own) in fast cars, which they enjoyed, having survived. He took multi-day bike trips in New England and ran the three-day Routeburn Track in New Zealand in one day. He played excellent bridge, even better tennis, but his best sport was skiing.
He was an adventurous sailor, skippering sailboats from Nova Scotia through Maine to the Hudson River. He took his NYC Boat Basin power boat up and down the Hudson River. He sailed in the Menemsha Races in a disreputable Sunfish.
He and his wife Julie had homes in Queenstown, New Zealand, and Nice, France. Miles’ true homebase as an adult, however, was the Jaffe family compound on Stonewall Beach in Chilmark, which his parents had assembled starting in 1952.
He was predeceased by his father, Louis Jaffe, Byrne Professor of Administrative Law at Harvard Law School, his mother, Mildred Miles Jaffe, a barrister of the English courts, and his sister, Deborah Jaffe Yeomans.
He is survived by his wife, Julie Jaffe, by his two step-sons, J. Max Simon, his wife Allison Simon, their daughter Violet of Chilmark, and David R. Simon and Tania Marie of Lake Tahoe, Calif. His remains will be buried at Abel’s Hill cemetery. By his request, there will be no formal funeral. In July, the family will announce a memorial service and celebration of his extraordinary life at home on Stonewall Road in Chilmark.
For online condolences and more information, please visit chapmanfuneral.com.