Splendid matte-finish 3.75 x 5.5 chest photo on its original 6.75 x 8.5 mount, signed and inscribed in ink on the mount as president, “W. A. Prendergast, Esq., With regards of Theodore Roosevelt, Jan. 21st. 1904.” The original recipient, William Ambrose Prendergast (1867–1954), was a New York political associate of Roosevelt’s who served as the longtime comptroller of New York City. According to a 1912 article in American magazine, Prendergast was “a man who could have been candidate for Governor of New York on the regular Republican ticket, and who was offered the Vice Presidency on the Taft ticket.” Prendergast instead threw his support behind Roosevelt’s Progressive candidacy, which split the Republican vote and landed Democrat Woodrow Wilson in the White House. A very subtle suggestion of toning to edges of mount and small, faint bend to lower right corner, otherwise fine, clean, fresh condition. An impressive, beautifully signed image with a most significant association! Auction LOA John Reznikoff/PSA/DNA and R&R COA.