In my opinion, the one that sent Patrick Roy and then-captain Mike Keane to the Colorado Avalanche for Jocelyn Thibault, Andrei Kovalenko and Martin Rucinsky ranks first because it put the Habs at the bottom of the standings for a decade and single-handedly eliminated the largest season ticket waiting list in sports to the point where the then-Molson Centre even had empty, unsold seats during home games, a feat that hadn't been achieved since the early 1940s.
Others put the Chris Chelios for Denis Savard trade first, but I won't, because the Habs still won the Stanley Cup in 1993. It wasn't an amazing trade by any means, but it didn't hurt that much.
And yet some classify the trade that sent projected future captain Chris Higgins, future star defenseman Ryan McDonagh, the just-as-taented Pavel Valentenko and Doug Janik for Tom Pyatt, Mike Busto and Scott Gomez as the worst, because it gave the New York Rangers their captain (McDonagh), rid them of their cap troubles, and because Gomez eventually went over a full calendar year without scoring a single goal, which eventually led to the Canadiens buying him out. Remember, Gomez was Plan B after Montréal failed to complete a trade with the Tampa Bay Lightning for Vincent Lecavalier - with strong rumours of Gary Bettman blocking the deal so the Bolts could more easily find themselves a new owner when those in place stopped agreeing.
My brother gave me his card collection last year, which included some cards I had originally given him myself, including this one of Gomez wearing the Habs' white (now-away) uniform with the Centennial patch on the right shoulder:
It also enshrines him as #91 in my Habs Numbers Project. My friends in the service industry liked him a lot - he's a great tipper.
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