From the turn of the twentieth century to the present day, few local institutions have navigated the neighborhood’s real estate evolution quite like Robert T. Fowler & Sons. Spanning three generations, the Fowler family business stands as a remarkable testament to the endurance of independent, locally focused enterprise.
Robert True Fowler, born in 1872, originally pursued a very different career path, graduating from the Yale Sheffield Scientific School with a specialization in “electrics” and working in the Kauri gum export business in New Zealand. After returning to Jamaica Plain, he joined his father-in-law’s firm as a clerk before opening an independent real estate and insurance business in March 1905, utilizing the famous slogan, “Ask Mr. Fowler.” The business expanded rapidly, adapting to changing times; Fowler famously upgraded his transportation from a bicycle to a horse and carriage, and eventually to a two-seater chain-drive Mitchell automobile in 1910 to show properties.
By the 1930s, Robert’s sons Robert Jr. and Richard had joined the firm. Richard temporarily left to serve in the U.S. Navy during World War II, where he miraculously survived a kamikaze plane crash on the deck of the USS Shea before returning home to the family trade. In the 1950s, the business relocated to its first-floor offices in the historic Queen Anne-style brick building at 743 Centre Street, which remains its permanent headquarters. Long before computers, they managed their booming inventory using a highly visual index card system spread across a massive wooden slatted board, and connected with the community by mailing out annual calendars featuring historic sailing vessels. Navigating the Great Depression, two World Wars, and the digital revolution, the firm relied on deep community trust. In 2015, under third-generation leadership, the business successfully pivoted to operate exclusively as the Robert T. Fowler & Sons Insurance Company, remaining a vital commercial anchor in Jamaica Plain.
Information compiled by Jenny Nathans for the Jamaica Plain Historical Society was used in compiling this story.