WINCHESTER – 75 years ago, President Roosevelt’s youngest son, John, a newly commissioned ensign in the Navy, left his Boston home to take up his duties in California. Before leaving, on Sept. 19, 1941, he visited Winchester to say good-bye.
Though not long a part of the community and not a resident, young Roosevelt had become popular in Winchester – even adding a touch of glamor – as assistant manager of the new Filene’s department store.
Had he come to town to promote his father’s politics, he might not have been too welcome. Winchester was highly Republican, and many disapproved of his father’s New Deal. But John Roosevelt was one member of the Roosevelt family who did not have political ambitions, and people liked him for his own sake.
Born in Washington in 1916 and graduated from Harvard College in 1938, Roosevelt went to work at the Filene's department store in Boston. He began learning the business as a stock clerk in Filene's famous bargain basement.
“That was the best training in the world,” he told the press in 1949.
In 1940, a salesgirl wrote to the Boston Globe that “John Roosevelt is Tops.” Working in the coat department when he was a stock boy, she watched as customers maneuvered to get his attention.
“All ages and types must have visited that department on the pretense of purchasing coats, just to see John.” And his reaction? “As nonchalant as an old owl. You see John never went high hat at any time.” All over the store, she said, he was well liked.
In March 1940, a new branch of Filene’s opened in the Locatelli Block in Winchester. It was an event for the town and a promotion to assistant manager for Roosevelt.
Prior to the store’s opening on the first weekend of March, Roosevelt visited the Winchester Star office. Editor T. Price Wilson was an outspoken critic of FDR and his “autocratic New Deal political rule.” During election years, he opposed Roosevelt in his editorials.
But John Roosevelt made a good impression on him. “He is a very nice, pleasant young man, and will undoubtedly make a most favorable Winchester contact for his firm.” Perhaps it helped that John Roosevelt was the son-in-law of a staunchly Republican Boston banker and himself had Republican leanings, though he maintained an apolitical attitude until after his father died.
At a party at the store on the night before opening day, the Star reported, “John Roosevelt, assistant manager, was naturally a center of attraction. One could always place John by the friendly crowd which surrounded him; not that a crowd was needed at all, for John is no shorty and was always able to see where he was needed even if he was unable to reach the spot.”
Echoing FDR’s fireside chats, “That crowd hanging over the balcony rail, greeting him in unison as ‘my friend,’ got a pleasant smile and liked it, and undoubtedly put him down on their list at once as a ‘regular.’"
Although sometimes called the store manager, Roosevelt was actually assistant manager, his boss being Hazel F. Berry, who remained with the store until the opening of the Belmont branch in April 1941.
In 1999, life-long resident Martha Speers remembered getting a job at Filene’s. “Guess who was the first manager of Filene’s–John Roosevelt, the President’s son. What a come-on that was. When I graduated from high school, I was going with Ed Porter, with whom I became engaged and actually married. He and John Roosevelt knew each other because they’d both gone to Harvard. And he called up John Roosevelt and said I’d like to have a job, and so I had an interview with John Roosevelt. Then I became a substitute sales lady at Filene’s. He was very tall, very, very, very nice, and very attractive.”
Roosevelt settled into the mercantile community, joining the Rotary Club and, early in 1941, assisting the Red Cross’s Disaster Preparedness and Relief Committee as chairman of clothing.
However likable he was, being the President’s son may have had its difficult moments, especially since 1940 was an election year. Twice as many in Winchester voted Republic than Democrat (except in Precinct 6). Editor Wilson and others continued their criticisms of FDR in the press. According to Bruce Stone’s History of Winchester, “youngsters teased [John Roosevelt] so unmercifully the school department had to warn them to stay away and leave the man alone.”
But if young Roosevelt had any problems due to the prevailing local political views, particularly the relentless criticism of the New Deal in the Star, it was certainly not reflected in the amount of advertising the store put into the newspaper.
Before America went to war, while FDR was promoting preparedness for defense and aid to the Allies, his youngest son, along with a large part of the American population, leaned toward non-involvement and pacifism. John Roosevelt was considering seeking classification as a conscientious objector.
However, as was revealed in 1945, his mother talked him round, reportedly saying “if you were the son of anybody else but the president, I’d not say a word to you. But you have a responsibility to your father and to the country such as no other boy would have.”
In 1941, he enlisted with the Navy, after which the national press reported Eleanor Roosevelt as saying her son "has very strong ideas against killing" but decided “that he would not find a world dominated by Hitler worth living in.”
Roosevelt remained with Filene’s until May. He was appointed an ensign in March. He spoke to the Rotary Club that April. In May, the Star announced, he was called to service. He then resigned his position at Filene’s.
“Mr. Roosevelt made many friends in Winchester,” Wilson reported, “both for himself and his firm. His leaving is generally regretted.”
Roosevelt served in the Navy from 1941 to 1946. He was initially assigned to shore duty with the Supply Corps but managed a transfer to sea duty and, promoted to lieutenant, served on board the aircraft carrier U.S.S. Wasp in the Pacific. He received a Bronze Star. After the war ended, he was a lieutenant commander in the Naval Reserve.
On at least one occasion during the war, he returned to Winchester. In November 1943, after having recently returned from sea duty, he was among four guest servicemen at a Boston Filene’s employees’ rally for the United Ward Fund campaign. That December, the Star noted that he and his wife spent some time visiting the Filene’s in Winchester.
The Winchester Rotary kept Roosevelt on its list of honorary members for the duration and included him among the Rotarian servicemen to whom they sent gift boxes. However, following the war, the Club had to acknowledge he was a past member. Though Roosevelt returned to business he did not return to Winchester or Boston but rather owned and operated a department store in Los Angeles. When he moved back to the East, it was to New York, not Massachusetts.
In 1958, Roosevelt attended the 50th anniversary of Filene’s Bargain Basement in Boston. However, it is unknown if he visited Winchester again.