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. 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 captained the team, based out of Toronto, which was known as the Crosse and Blackwell Chefs following a sponsorship with a local food products company. Conacher recruited former amateur players who had likewise left the sport in favour of paying jobs in other pro sports, including his brother Charlie. The first game was held Thanksgiving Day in 1933, an exhibition contest against the Rochester Arpeakos. A crowd of 10,000 attended the game to watch Conacher play his first competitive football game in Canada in ten years. He did not disappoint, scoring two touchdowns and setting up a third for the Chefs, and was hailed as the game's star despite an 18–15 loss. Toronto lost a return match in Rochester, but in the third and final game of their season, the Chefs defeated a team from Buffalo at Toronto by a score of 18–0.