Toronto Maple Leafs and Canadiens make for unlikely trade partners

MONTREAL, QC - NOVEMBER 18: Jeff Petry /
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Toronto Maple Leafs
5 Jan 1995: Center Paul DiPietro of the Toronto Maple Leafs moves down the ice during a game against the Buffalo Sabres at Memorial Auditorium in Buffalo, New York. Mandatory Credit: Rick Stewart /Allsport /

1995 – Leafs send a draft pick to Montreal for Paul DiPietro

Paul DiPietro was a fifth round draft pick in the 1990 NHL Entry draft that would help make history for the Canadiens.

He spent three seasons in Montreal, where he recorded 25 goals and 44 assists in 154 regular seasons games. But it was in the playoffs where DiPietro would leave his mark in Montreal.

DiPietro was a part of the Canadiens team which won the Stanley Cup in 1993, when he scored eight goals and five assists in 17 playoff games; including two goals in the cup-clinching game against the Los Angeles Kings.

In April 1995, the Toronto Maple Leafs sent a 1996 fourth round pick to Montreal (Kim Staal) for DiPietro.

DiPietro couldn’t recapture his playoff magic for the Leafs, playing in only 32 regular season games over two seasons in Toronto with 10 points. In seven playoff games in 1995, he would score two points.

For Montreal, Staal would not make it to the NHL and has played over 20 years across Europe.