One of baseball’s most colorful and beloved characters, Hughie Jennings captained the Baltimore Orioles to four straight appearances (1894 to 1897) in the 19th century Temple Cup Championship Series. He came up to the majors with the Louisville Colonels, but enjoyed his best years with the brawling Orioles of John McGraw, Willie Keeler, Joe Kelly and Wilbert Robinson. During his tenure in Baltimore, he never hit below .328 and achieved a high mark of .398 in 1896, the major league record for shortstops. He batted .314 over a 17-year big league career. He managed 16 seasons in the majors, capturing three straight pennants with Detroit from 1907 to 1909.