3. The Craig Rivet Trade
The Montreal Canadiens were in a tough spot in the 2006-07 season, especially as the trade deadline neared. They were not really considered a huge Stanley Cup contender, but they had an elite power play that was carrying them in a season where power plays were plentiful.
They also were getting strong goaltending from Cristobal Huet and it gave them a chance to make the playoffs at least. They had snuck into the postseason the previous season and made life difficult on the Carolina Hurricanes in round one before Saku Koivu was injured and then the Hurricanes went on to win the Stanley Cup.
What made things difficult around the trade deadline was three of the Canadiens best defensemen were all pending unrestricted free agents, but the team was on the cusp of qualifying for the playoffs. They couldn't really trade all of Andrei Markov, Sheldon Souray and Craig Rivet, but they couldn't afford to lose them all for nothing in the offseason either.
With a tight salary cap at that time, there was no way they could afford all three either. So, they elected to trade Rivet to the San Jose Sharks for a first round pick, and Josh Gorges. The Canadiens ended up missing the playoffs by a single point, but the short term pain was outweighed by the long term gain of this deal.
Gorges turned into a top pairing defender for the Canadiens, often playing alongside P.K. Subban and taking on a ton of minutes at even strength and the penalty kill. Also, the first round pick was used to select Max Pacioretty.
Pacioretty was the best goal scorer on the Canadiens for nearly a decade and made the trade a steal of a deal for the Habs. They may have just missed the 2007 playoffs because of this deal, but they would not have made it in 2013, 14, 15 or 17 without Pacioretty leading the team's meagre offense all those years.