Al Smith was a well known New York politician whose trademark was the derby cap. In 1928, Smith was named the democratic presidential candidate. During his campaign Smith requested the help of Lou Gehrig and Babe Ruth, two famous New York Yankees. Ruth and Gehrig were the core of a Yankees line-up which was dubbed Murderer’s Row. The two potent hitters were fresh off of a World Series title when they began to campaign for Al Smith. Both Ruth and Gehrig wore a derby cap as a symbol of support for Smith.

This derby cap was worn by Gehrig while campaigning for Al Smith throughout the state of Ohio. It is a brown derby style cap that is lined in silk and bound with a tan leather band. A black ink stamp adorns the inside crown, reading The Union. The outside base of the hat is laced in ribbon while the leather brim is stretched and folded. Gehrig is noted for wearing a navy melton wool cap with an embroidered NY while playing in 2,130 consecutive games. However, this rare piece, which was offered at auction by Sotheby’s, shows the magnitude of Gehrig as a public figure away from the baseball diamond.