Four (4) Theodore Roosevelt related buttons and pins, including two (2) Governor of New York campaign buttons, 1898, and one (1) "Big Stick" pin. 1st item: Gubernatorial campaign button, 1898, depicting a bust portrait of Roosevelt in uniform with blue lettering reading "FOR/GOVERNOR/THEODORE/ROOSEVELT" top and bottom right against an off white and grey background with draped American flag border. Maker's marks dated 1898, lower edge. Retains Wm. F. MIller and Company New York, back paper. 1 3/4" dia. 2nd item: "Big Stick" pressed metal pin, rendered in the shape of a large club or stick with embossed initials reading "T. R." to base. 2 3/8" L. 3rd item: Gubernatorial campaign button, 1898, depicting a bust portrait of Roosevelt in uniform with black lettering reading"ROOSEVELT" against a gold background. Maker's marks dated 1898, lower edge.Retains Whitehead and Hoag,Newark, New Jersey back paper. 1 1/4" dia. 4th item: EdwardSydney Stuart gubernatorial campaign button, 1906, depicting a bust portrait vignette of Stuart against a portrait of Roosevelt with an American flag surrounded by blue lettering reading "FOR THE REPUBLICAN PARTY AND PROSPERITY/FOR GOVERNOR EDWIN S. STUART" against a light blue background. Does not retain back paper. 13/16" dia. Provenance: Private Southern estate. CONDITION: All items in overall good condition with surface scratches, minor surface dents. Toning/dampstaining to back papers. 1st item: Vertical surface scratches to surface, possibly in the making.