One of baseball’s most colorful and best-loved characters, Jennings rose from breaker boy in the Pennsylvania anthracite fields to the Hall of Fame. The redheaded, freckled firebrand wore a major league uniform for more than three decades as a player, coach, and manager. He also earned a law degree and built a successful off-season legal practice. Jennings’s best years came as captain of the powerful, brawling Baltimore Orioles, National League champions in three straight years, 1894-96 and winners of the 1897 Temple Cup. Operating within and outside the rules, Jennings and teammates John McGraw, Willie Keeler, Joe Kelley, and Wilbert Robinson were the scourge of opponents and umpires. During his five full seasons in Baltimore, Jennings never batted below .328 and achieved a high of .398 in 1896, the ML record for shortstops. In addition, he stole as many as 70 bases in a season and was the leader in fielding average and putouts three times each.
His hitting declined in later years, and a sore arm forced a move back to first base, but Jennings’s superior skills as a strategist and field leader kept him steadily employed. He played for pennant winners in Brooklyn in 1899 and 1900, and later captained the Phillies before embarking on a managing career in the minors. Purchased by the Tigers in 1907, Jennings guided the team to pennants in his first three years at the helm. The Tigers lost all three World Series, however, and never again won a pennant under Jennings, who remained on the job through 1920. From the third base coaching box, the hyperactive skipper prodded his charges, among them the young Ty Cobb, and taunted the opposition with shouts, whistles, and gyrations. His piercing yell of “Ee-Yah” became a trademark. Upon leaving the Tigers, Jennings was signed by former Oriole teammate John McGraw as a coach and assistant manager with the Giants. In the role of right-hand man, Jennings was a part of four consecutive pennant-winning clubs (1921-24).
Though durable, Jennings suffered an incredible string of mishaps on and off the field. He was often hit by pitches; a then-record 49 times in 1896 alone. Two skull fractures, one the result of an accidental dive into an empty swimming pool, slowed but did not stop him. A nervous breakdown after the 1925 season, however, brought his baseball days to an end. He was elected to the Hall of Fame in 1945.