Playing Career
Jack began his career with Alloa Athletic, making his debut at the age of 15 and turning professional in 1893. He moved to Bolton Wanderers in 1895. He was Bolton's leading scorer in the 1896–97 season with 11 goals. He played a total for 110 league and 15 FA Cup games for the club, scoring 29 goals. He left Bolton in August 1901, following a serious ankle injury. He joined local rivals Preston North End after scoring 29 goals in 110 league games for Bolton. He spent just one season with Preston, scoring 6 goals in 22 league games, before joining Glossop the following summer. After a further 6 goals in 30 appearances he moved to Plymouth Argyle, becoming the club's first professional in 1903. He made his Argyle debut in September 1903 against West Ham United in the Western League. In 1904–05, the club's handbook described him as "our famous flier, probably last season was the best in the player's history".
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