Sept. 23, 1908
Starting for the New York Giants for the first time in his career, Fred Merkle (at 19, the youngest player in the National League in 1908) committed a colossal baserunning error that would follow him for the rest of his lengthy career. Standing on first in the bottom of the ninth of a 1-1 tie, Merkle assumed he didn't have to touch second base when the winning run was blooped in. As he trotted back to the dugout the ball was thrown to second and Merkle was called out, costing his team the victory. The play, nicknamed Merkle's Boner, cost the Giants a pennant.