player-coach in , but his play and health had deteriorated. Two events in that off-season saved Conacher: he swore off alcohol completely upon the birth of his first child, and his playing rights were sold to the Montreal Maroons. Conacher periodically struggled with Montreal, and at one point was placed on waivers with no other team willing to take over his contract. Nonetheless, his overall play and point totals increased for three consecutive seasons with the Maroons, peaking at 28 points in . He was named to the second All-Star team that season, but was traded to the Chicago Black Hawks in exchange for Teddy Graham. Conacher was a key figure in the club's first-ever Stanley Cup victory that season. He finished second to the Canadiens' Aurel Joliat in the voting for the Hart Trophy and earned a spot on the NHL's first All-Star team. On Wednesday October 3, 1934, Conacher was involved in one of the largest transactions in league history. He was dealt to the Montreal Canadiens, along with Leroy Goldsworthy and Roger Jenkins in exchange for Montreal superstar Howie Morenz, Lorne Chabot and Marty Burke. The deal was only part of a series of trades involving four teams that represented one of the biggest deals in NHL history. Immediately following the Chicago trade, Conacher was sent back to the Maroons, along with Herb Cain, in exchange for the rights to Nelson Crutchfield. Conacher spent his last three NHL seasons with the Maroons and won his second Stanley Cup in 1935. He ended his hockey career after the team was eliminated from the playoffs by the New York Rangers on April 23, 1937. That final year he was runner-up to Babe Siebert in the 1937 Hart Trophy voting and was placed on the NHL second All-Star team. Canadian professional football Conacher had not played competitive football since turning professional. At one point he was offered a position as coach of the Montreal AAA Winged Wheelers, but disappointed the Interprovincial Rugby Football Union club when he turned down the job due to his other commitments. He was not absent the game long, however, as Conacher returned to football in 1933. He was part of an effort to launch a new professional league that would feature both Canadian and American teams. The league never came to fruition, but Conacher organized what became the first professional football team in Canada. He