It’s been many moons since the Montreal Canadiens and Toronto Maple Leafs were involved in a trade. In fact, the last time it happened was back in the summer of 2008. The Habs sent centre Mikhail Grabovski to Toronto in exchange for Greg Pateryn and a second-round pick in 2010. That pick eventually got back to the Leafs via trades with Chicago and later Boston while Pateryn was moved to Dallas last season for Jordie Benn.
However, deals between the Leafs and Habs have happened a lot over the years. Think back to moves involving Doug Gilmour, Frank Mahovalich, or Darvey Tucker.