Every now and then, a trade goes so wrong for a team that it negatively impacts the franchise for years to come. In June 2009, the Montreal Canadiens made such a deal when they acquired Scott Gomez as part of a seven-player trade.

It’s a move easy to criticize In hindsight, but even at the time it was a questionable as Gomez came with an annual cap hit of roughly $7.4 million through the 2013-14 campaign. In the end, Gomez tanked so badly in Montreal that the team refused to let him play last season, for fear that he might get hurt before Montreal could use an amnesty buyout on him. The NHL and players association got together to allow the Canadiens to buy him out early as a compromise.

And yet, even with him gone that trade still haunts them because one of the players they gave up, 2007 first round pick Ryan McDonagh, has flourished with the Rangers. In Game 1 of the Eastern Conference Final, the 24-year-old defenseman gave the Canadiens a taste of what they missed out by scoring a goal and three assists in the Rangers’ 7-2 victory.