A descendant of both John Winthrop, first Governor of Massachusetts, and John Winthrop, the Younger, first Governor of Connecticut, immediately after graduating he became a personal secretary to future president William Howard Taft while Taft was Governor-General of the Philippines. Winthrop was soon promoted to Assistant Executive Secretary of the Philippines (1901–1903) and was appointed as a Judge of the Court of First Instance, Philippine Islands (1903–1904). He was known to be a personal friend of Theodore Roosevelt and was appointed by him in 1904 as Governor and General Commander of Puerto Rico, at age 28.[2][3][4] He was confirmed by the Congress.[5][6] Melza Riggs Wood (1870–1928), four years his senior, whom he married in 1903,[7] became the First Lady of Puerto Rico.
Winthrop took oath as governor of Puerto Rico on July 4, 1904, and served until April 17, 1907.[8] On his inauguration, he promised improvements to the educational system of Puerto Rico. Winthrop was a proponent of bringing citizenship and locally elected officials to Puerto Rico system of governance.[9] The press reported favorably on Winthrop's activities, and reporters were especially impressed with Mrs. Winthrop's fluency in Spanish, which made her popular among local population.[10]
Following his retirement from public service in 1913, he was a director of National City Bank. He resigned from the bank in 1916.[13] He subsequently became a senior partner of Robert Winthrop & Co. in New York, from which capacity he stepped down in 1939. At the end of his life he lived in New York on East 69th Street,[14][15] where he died on November 10, 1940.[16] He is buried at Green-Wood Cemetery.
The Winthrops did not have children, however, Nathaniel Thayer Winthrop, a son of Frederic Bayard Winthrop, named his son, Beekman Winthrop (1941–2014) to honor his uncle.[17]
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