Robert G. Caldwell Jr., a retired CIA officer and longtime Chilmark resident, died April 4 at the age of 91. Born in Columbus Grove, Ohio, on August 24, 1917, Bob was the son of Edith R. Jones and the historian and diplomat, Robert G. Caldwell Sr. and husband of Ruth (Roo) Farrow Caldwell.
Bob first came to the Vineyard with Roo when they were courting in 1950. This was the beginning of two enduring loves that sustained him throughout his lifetime — for his beautiful wife and the lovely Island of Martha’s Vineyard, where her family had been summering since the 1930s.
Bob graduated from Yale in 1940 with a degree in international relations. During World War II, he served in North Africa and Europe. In November 1942, he landed in the assault wave at Fedala, French North Africa. Later he participated in the invasion of Southern France with the Seventh Army in August 1944 and was awarded a combat commission as a second lieutenant. Attached to the first airborne task force, he was put in charge of counterintelligence for southeastern France. In December 1944, he was transferred to the headquarters of the twelfth armored division. His unit assisted with the reduction of the Colmar pocket in the drive to the Rhine. He was promoted to first lieutenant in June, 1945, and later made commanding officer with the 512th C.I.C. detachment of the twelfth armored division.
Inspired by his father’s interest in foreign affairs and like many who worked with the CIC, the Counter Intelligence Corps during the war, Bob went on to join the Central Intelligence Agency. He served overseas mainly as a political officer and chief of station. His posts abroad were as follows: Tangier, Cairo, Damascus, Beirut, Saigon, Nicosia, and Tunis. Bob resigned in August 1973, but continued to work in External Liaison until July 1975. In his career, he was pragmatic and clear-sighted about the challenges facing our nation, but he was unwavering in his belief that we must always hold true to our fundamental values. His compassion and extraordinary ability to connect with people distinguished him throughout his life and benefited our country in countless ways.
Throughout his years serving abroad, the Vineyard was the umbilical center for family life and in 1979, Bob and Roo retired to the house they built near Prospect Hill in Chilmark. Here they delighted in birding and reveled in all the seasonal rituals of Island life from scalloping to fishing. Bob enjoyed building stone walls and tending his lovely collection of bonsai trees. He was also active in community life; he served on the finance committee and the conservation commission for the town of Chilmark. Most of all, he gave guidance and solace to many in the Island community as a true friend.
He taught all of his children how to love and be passionately interested in so many wondrous aspects of this world. Surviving Bob are his two sisters, Alice Fenney and Janet Klos; his four children Duncan Caldwell of Paris, France, and Aquinnah, Susanna Linfield of Miami, Fla., Edward Caldwell of West Barnstable, Jennifer Fisher of San Francisco, Calif., and eight grandchildren.
The Caldwell family extends heartfelt thanks to all our many Island friends who make this beautiful Island such a cherished home. Please join us at 9 a.m. on August 8 for a memorial service at Abel’s Hill Cemetery in Chilmark.
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