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To Harvard, Inevitably. Dillon went on to Groton, where he graduated second in his class, and then, inevitably, to Harvard. Around the Yard, recalls a former professor, he was known as "a terribly able fellow." Too weedy to play football, he managed the freshman and varsity teams, played squash and tennis (when he was 15. he had qualified for the National Junior tennis championships). Dillon's academic interest was American his tory and literature. He had no care then for fiscal theory, and even now likes to boast that "I never took a course in economics in my life."
Dillon was a bridegroom before he was a bachelor (of arts). Three months be fore he graduated magna cum laude, he married pretty, buoyant Phyllis Chess Ellsworth of Boston. Doug took his bride on a European honeymoon, stopping off at Monte Carlo to try out his system for winning at roulette. The young couple cashed in enough chips to buy a set of Napoleon-era china, which they still use —but the future custodian of untold U.S. billions decided that the system was "too boring." and has not used it since.
Before World War II, Dillon made many trips to France; a favorite stopping point was Chateau Haut-Brion, a 104-acre estate in Graves that produces one of the most subtle and exhilarating wines of Bordeaux. Once owned by Talleyrand, the chateau had been bought by Dillon's father in 1933. Over the years, Doug Dillon has taken deep personal interest in the property, and still reserves a large share of Haut-Brion's output for his own use. He takes a connoisseur's quiet pride in his knowledge of wines. "I can tell the year of a given Bordeaux or the district it came from," he says, "but I can't spot both the year and the vineyard."
Parental Shadow. In 1931 Dillon bought himself a seat on the "big board" with a fatherly gift of $185,000, served an apprenticeship with smaller investment houses before joining Dillon, Read as a junior partner. The parental shadow loomed large over the firm—the Baron was board chairman—but Doug Dillon proved that he could hold his own as a Wall Street expert. When Britain, at the start of Lend-Lease, was trying to dispose of some U.S. corporate assets, he took on the delicate $40 million deal that set the American Viscose Corp. (until then a subsidiary of Courtaulds, Ltd.) on its own feet. Dillon, who was then 31, handled the complex transaction without a flaw.
In 1940 the president of Dillon, Read, James V. Forrestal (later the nation's first Defense Secretary), went to Washington as Under Secretary of the Navy.*Doug Dillon went along with him, helped form the Office of Strategic Services (predecessor of the CIA), spent three frustrating years behind a desk before he wangled an escape into action in the southwest Pacific. Serving as an air-operations officer of the Seventh Fleet, Dillon flew on "black cat" (night reconnaissance) missions, took part in bombing runs against Japanese installations in the Philippines. "We were shot at a little," he recalls modestly. "I know what tracers look like." By the time he was mustered out, Dillon had risen from ensign to lieutenant commander.