Sheckard was one of a handful of Pennsylvania Dutch to play in the majors. Though chiefly remembered for his years with the Cubs, for whom he played in four World Series, Sheckard had his best years with Brooklyn. He batted .353 while leading the league with 19 triples and a .536 slugging percentage for the 1901 Brooklyn Superbas; his 11 HR and 104 RBI were career highs. In 1903 his nine HR were enough to capture the NL title, and he tied for the league lead with 67 stolen bases. (With Baltimore in 1899, he had led the NL with 77 stolen bases.) With the Cubs, he embarrassed himself in the 1906 World Series; boasting that he would bat .400 against White Sox pitching, he instead went 0-for-21 as the Sox upset the Cubs in six games. In 1911 he set a Cub record for most walks (147), leading the NL for the first of two straight seasons. He also scored an NL-high 121 runs that year.