 Gerry inherited large real estate holdings from his mother, who died in 1920, which Gerry and his elder brother agreed to sell in 1922.In a 1918 trust agreement, the brothers and their sisters, Angelica Livingston Gerry and Mabel Gerry, could all exchange ownership in Gerry real estate for stock in the Gerry Estates, Inc.

Gerry was elected to the United States House of Representatives for Rhode Island's 2nd District as a Democrat from 1913 to 1915.He was an unsuccessful candidate for re-election in 1914, but he was elected to the United States Senate in 1916 and served from 1917 to 1929.