This trade, though one-sided, doesn’t make the list because at the time, Cullen was a dominant player. At the time of the trade, he was 27 and had 94 points in just 65 games. Nobody could have guessed he would fall apart two years later.

The List

10.  Oct. 4, 1991: Edmonton trades Mark Messier and Jeff Beukeboom to the Rangers for Bernie Nicholls, Steven Rice, and Louie Debrusk

Even if Edmonton was rebuilding after its dynasty, it’s hard to rationalize this trade. Messier was one of the best players in the NHL, and Edmonton was compensated with 30-year old Bernie Nicholls (a good player, but useless for a rebuilding team) and two prospects that never panned out (Steven Rice and Louie Debrusk).

There was an interview on WFAN (the New York City sports radio station) with former Rangers GM Neil Smith which touched on this trade. Smith explained that at the time, those interested in Messier were worried about the wear and tear on his body.

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