Toronto Maple Leafs and Canadiens make for unlikely trade partners

MONTREAL, QC - NOVEMBER 18: Jeff Petry /
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Toronto Maple Leafs
TORONTO, ON – NOVEMBER 13: Doug Gilmour /

2003 – Doug Gilmour returns to Toronto

Doug Gilmour is one of the most beloved players in Leafs’ history and the opportunity to have him return to Toronto in 2003 had fans everywhere in a frenzy.

Gilmour was the face of the franchise from 1992 to 1997, leading the Leafs to back-to-back conference finals appearances in 1993 and 1994. This was the closest any Leafs captain has been to guiding the team back to the Stanley Cup Finals since 1967.

Which was why it was so heartbreaking for Leafs nation when it was announced that Gilmour had been traded to the New Jersey Devils for Steve Sullivan, Alyn McCauley and Jason Smith in 1997.

In 393 regular season games Gilmour scored 131 goals and 321 assists, along with 17 goals and 60 assists in 52 playoff games.

After spending time in New Jersey, Chicago and Buffalo, Gilmour signed with the Canadiens in 2001 as a free agent.

In two seasons with Montreal, Gilmour showed he still had something left in the tank, scoring 71 points (21 goals, 50 assists) in 131 regular season games and 10 points (6 goals 4 assists) in 12 playoff games.

When then Leafs general manger Cliff Fletcher sent a 2003 sixth round pick to Montreal for Gilmour everyone expected a storybook ending for the former captain, but it never came.

Rejoicing turned quickly into heartbreak as Gilmour tore his ACL in his first game back in Toronto, which would ultimately be his last.

Meanwhile for Montreal, the sixth round pick turned into defenceman Mark Flood who never played for the Canadiens and played only 39 games in the NHL with the New York Islanders and Winnipeg Jets. He last played in the NHL with the Jets in the 2011-2012 season.