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NHL Trade Deadline: Ranking every team’s worst ever trade

By David Rouben

SACRAMENTO, CA - APRIL 3: Wayne Gretzky of the Los Angeles Kings in action against the Edmonton Oilers at the Arco Arena on April 3, 1994 in Sacramento, California. The Kings defeated the Oilers 6-1. (Photo by Rocky Widner/Getty Images)
SACRAMENTO, CA - APRIL 3: Wayne Gretzky of the Los Angeles Kings in action against the Edmonton Oilers at the Arco Arena on April 3, 1994 in Sacramento, California. The Kings defeated the Oilers 6-1. (Photo by Rocky Widner/Getty Images) /
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19 Jan 1996: The Boston Bruins take on some past Heroes of Hockey in an exhibition the day before the NHL All Star Game at the FleetCenter in Boston, Massachusetts. Rick Middleton
19 Jan 1996: The Boston Bruins take on some past Heroes of Hockey in an exhibition the day before the NHL All Star Game at the FleetCenter in Boston, Massachusetts. Rick Middleton /

29: New York Rangers

Rick Middleton is a Bruins legend, having played 12 full seasons with them and setting all kinds of goal scoring records. His time in New York has become a footnote, while the hindsight on this deal has come back to haunt the Rangers to this day.

Middleton had a sparkling junior career, and the Rangers were lucky that he fell to 14th in the draft. He put up respectable numbers in his first season – 40 points despite having injuries limit him to 47 games – then 50 points in 77 games the season after that. The Rangers decided to trade him because they felt that was underwhelming, and got back Ken Hodge who was near the end of his career.

The Rangers should’ve known better. Middleton was only going to improve after that season, and even though Hodge won multiple Stanley Cups with the Bruins, he went from 105 regular season points to 66 and then 61 in the seasons before he was dealt. He was only able to provide the Rangers one full season in which he scored 62 points before calling it a career.

Rick Middleton, meanwhile, developed well with the Bruins. In fact, in his first game in a Yellow and Gold uniform, he scored a hat trick and hit the 90-point mark in five straight seasons. He won a Lady Byng and set points records in the playoffs – including scoring 19 points in a single series against the Sabres. He also tied the record for most points in a single season by a right winger with 105 in 1983-84. He holds that record with … you guessed it, Ken Hodge. The only reason he didn’t win a Cup was because the Islanders and Oilers reigned supreme during the 80s.

The Rangers finally ended their nearly 54-year long Stanley Cup drought in 1994, but had they kept their faith in Rick Middleton, it could’ve ended much sooner than that.

Next: 28: Ottawa Senators

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