On this August 19, 2021, we celebrate the 27th anniversary of one of the worst transactions the Montreal Canadiens ever made. The worst one to date is easy, it's the one of December 6, 1995, when the Habs traded Patrick Roy and Mike Keane in exchange for Jocelyn Thibault, Andrei Kovalenko and Martin Rucinsky from Colorado.
The one involving Chris Chelios and a 2nd pick in return for Denis Savard, is also among the worst. At the time, in 1990, Chelios' knees were said to be done, even though he was only 28 years old... Well, he played another 19 years after that, which shows that the singer Bob Bissonnette's words are close to the truth.
We can also bring back Bob Gainey's worst move in his long managerial career, the one where he got rid of prospect Ryan McDonagh in a monster trade involving, among others, Scott Gomez. Or the one that got John LeClair, Gilbert Dionne and Eric Desjardins out of Montreal in order to get Mark Recchi.
In short, most general managers have had bad moves. The one that we present today was made by Serge Savard, when he traded Guy Carbonneau to the Blues on August 19, 1994 in return for Jim Montgomery (only five games with the Habs and 122 in the NHL). Carbo left the organization shortly after his middle finger was shown on the cover of the Journal de Montréal.
Ah yes! One I also remember is the one involving Mike Ribeiro who was traded for his attitude and reputation as a party animal in exchange for, get this, Janne Niinimaa. Picks were also involved on both sides.
