When his father died in 1925, Gerald shared his father’s $10 million estate, with his two sisters, Mary and Abbie Frances. With the Livingston investment business established, Gerald had married Eleanor Rodewald, settling into their Gilded Age Upper East Side townhouse and sharing a passion for the sporting life, becoming a presence at Nassau County dog shows and Piping Rock horse shows. In 1919 Gerald and Eleanor Livingston bought Kilsyth Farm in Lloyd’s Neck for $125,000, quickly making it the center ring for hunting dog competitions. After the Livingston Company merged in 1934 with Abbott, Proctor and Paine, Gerald and Eleanor spent more time raising, training and showing their dogs, every January heading to their North Florida-Georgia plantation near Thomasville, where Gerald's father Crawford, earlier had become a member of Thomasville Country Club set.