After attending Fordham University, he embarked on a baseball career that would last 70 years. He made his first appearance at the major league level by signing and playing two years for the Columbus Solons of the American Association. Doyle would play for ten clubs from to, batting.299 in 1,569 games with 518 stolen bases. He began as a catcher-outfielder and became a first baseman in. His best years were in 1894, when he batted.367 for the New York Giants, and in, when he hit.354 with 62 stolen bases for the Baltimore Orioles. He is credited with being the first pinch-hitter in pro ball, with Cleveland at Brooklyn on June 7,. Patsy Tebeau was the manager and Doyle came through with a game-winning single. For the season, he took over the everyday duties at first base and became team captain . Manager John Montgomery Ward not only make the decision to replace his former teammate and friend Roger Connor, but released him as well. Connor was a very popular player, and this decision drew the ire and scrutiny from the fans and media alike. Ward defended his decision, and claimed the move came down to the fact that he liked Doyle's playing style, describing him as a hustler. Replacing Connor at first base proved worth the risk as Jack batted.367 that season, and he totaled 100 runs batted in, and stole 42 bases.
Dirty Jack
Because of his aggressive playing style, Doyle was known as "Dirty Jack", often feuding with umpires, fans, opposing players, and even, at times, his own teammates. On one occasion, in Cincinnati on July 4,, while in the 3rd inning of the second game of a doubleheader, Doyle slugged umpire Bob Emslie after being called out on a steal attempt. Fans jumped from the stands as the two got into it, and players finally separated the two fighters. Two policemen chased the fans back into the stands and then arrested and fined Doyle. On July 1,, when he was being harassed by a Polo Grounds fan, he jumped into the stands and hit him once with his left hand, reinjuring it after having broken it several weeks earlier. He carried on a lengthy feud with John McGraw that started when they were teammates at Baltimore. McGraw, of course, had to have the last word. In, McGraw was appointed manager of the Giants, and his first act was to release Doyle, even though he was batting.301 and fielding.991 at the time. Even with these seemingly out-of-control traits, Doyle was deemed a natural leader and was selected as team captain in New York, Brooklyn and Chicago, and served as an interim manager for the Giants in and Washington Senators in.
In 1905, after playing one game with the New York Highlanders, Doyle became manager of Toledo of the Western Association. One year later, in, he was named the manager of the Des Moines Champions, so named because they won the league championship the previous year, and they won it again under Doyle's helm. Following his championship season at Des Moines, he managed Milwaukee in
