Because the topic often comes up, I thought I'd give my two cents worth. As always, feel free to disagree with the order, or perhaps even add your own nominations.
1. Rick Middleton to the Boston Bruins for Ken Hodge: This trade has often been compared to the Mets sending Amos Otis to the Kansas City Royals for Joe Foy. But it's actually much worse. The Mets had won the World Series and had Tommie Agee in centerfield. Ed Charles had just retired and the Mets weren't sure if Wayne Garret could handle playing 3rd base full time, so you could almost forgive them for wanting to shore up what they perceived was a weakness on the infield.
There is no such absolution for the Rangers. They were clearly in rebuild mode entering the 1976-77 season. John Ferguson was now in his second year as GM. Middleton was a young winger with enormous potential, while Hodge was a seasoned veteran whose best years were well behind him. Aside from the fact that Hodge had played with Phil Esposito during his Bruins days, there was simply no justification for making this trade. None.
2. J.T. Miller and Ryan McDonagh to the Tampa Bay Lightning for Libor Hajek, Brett Howden, Vlad Namestnikov, 2018 1st-Round Pick and 2019 2nd-Round Pick: The decision by Jeff Gorton to rebuild in the winter of 2018 was, in retrospect, the correct one. The window for this core was clearly closing, so it was time to break up the band. Where he fouled up was the return he got. Steve Yzerman clearly fleeced him on this deal. Of the three players who came over from the Lightning, only Howden - now a member of the Vegas Golden Knights - has had anything remotely resembling a successful NHL career. And the draft picks the Rangers received didn't amount to much either.
McDonagh, meanwhile, played an integral role in helping Tampa win two consecutive Stanley Cups, while Miller has become one of the NHL's premier centers, albeit playing for the Vancouver Canucks. By re-acquiring Miller last week, you could say Chris Drury has at least partially atoned for Gorton's mistake, though seven years after the fact.
3. Mike Ridley and Kelly Miller to the Washington Capitals for Bobby Carpenter: On paper, this trade made perfect sense. Phil Esposito had replaced Craig Patrick as Rangers GM and was looking to make his bones. Carpenter checked all the boxes: size, speed, you name it. It should've been a slam dunk. Except Carpenter was a flop on Broadway, registering a measly 10 points in 28 games before Espo dealt him to the LA Kings for Marcel Dionne.
Ridley and Miller, on the other hand, would go on to have successful careers playing for the Caps, while Carpenter eventually finished his career with the New Jersey Devils, a shell of the player the Rangers thought they were getting when they traded for him. The moral of the story is quite simple: the grass isn't always greener on the other side of the street.
4. Sergei Zubov and Petr Nedved to the Pittsburgh Penguins for Ulf Samuelsson and Luc Robitaille: The post Stanley Cup years were very difficult ones for Neil Smith. At times, he didn't know which direction he wanted to take: retool or stay with the core. After the Rangers got swept by the Philadelphia Flyers in '95, he panicked and traded two of his more talented players for an admittedly physical defenseman and a veteran forward whose best years were behind him.
Zubov would go on to win another Cup with the Dallas Stars in 1999, while Nedved enjoyed his best season playing on a line with Mario Lemieux and Jaromir Jagr. Oh, and by the way, the Pens beat the Rangers 4-1 in the second round of the '96 playoffs. Sometimes the best trades are the ones you don't make.
5. Jean Ratelle and Brad Park to the Boston Bruins for Phil Esposito and Carol Vadnais: After the Islanders upset the Rangers in the 1975 preliminary round, it was clear this core was done. Emile Francis knew in his heart what he needed to do and that was rebuild. Instead, he swapped stars with the hated Bruins.
While Espo and Vadnais played an integral role in the Rangers getting to the finals in '79, there's no denying the fact that Boston got the better of this trade. Ratelle, Park and Middleton (see above) gave fans in Beantown years of excitement, while Rangers fans had to endure three seasons of misery until some of their younger players developed under a new front office regime.
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