Born and raised in Toronto, Jack Shill played for the Toronto Marlboros in the OHA from 1929 to 1933. He made the jump to the NHL for the 1933-34 season, with the Maple Leafs, of course.
Shill played nine games that season for the Leafs while playing the majority of the year with the Marlies. He was loaned to the Boston Bruins for the 1934-35 season where he played 45 games with the NHL club. Shill then returned to the Leafs for the next season, only to play the majority of his games with the IAHL's Syracuse Stars where he became a first all-star team member.
The 1936-37 season marked Shill's first full year with the Leafs before being traded to the New York Americans prior to the 1937-38 season. After playing 22 games for New York, Shill was traded to the Chicago Blackhawks where he finished the regular season as a Hawk and helped the team in the post season. The Hawks faced Shill's recent team, the Americans, in the semi-finals and sent them home after winning two games to one. In the Stanley Cup finals, the Hawks faced yet another former team of Shill's, the Leafs. Chicago claimed its second championship and Shill's first and only Cup.
Shill played one more season in the NHL before moving on to the AHL and finally hanging up his skates in the 1942-43 season.