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Reactions
CNNSI.com asked if Red Wings fans had any opinions on the subject. And guess what ... they did.

Click here to read a sampling of what CNNSI.com users had to say. 

 
Sports fans love to reminisce over the days when it all went wrong: the wasted draft pick, the tragic trade or the defecting hero. These may not be, by definition, the worst roster moves ever made, but they were the ones that affected us on a personal level. These are the events that caused -- and still cause -- us to sit on our bar stools and lament the cruel twists of life.

Life-long Red Wings fans Craig Barker and Dave Wallace submitted their five all-time heartbreakers, starting with the 1989 trade of young Adam Oates, followed by the 1957 trade of Cup heroes Glenn Hall and Ted Lindsay, the drafting of Keith Primeau, the trade of Marcel Dionne and the multi-player trade that supplied Edmonton with the backbone of its 1990 Cup run.

 
June 15
1989 
Detroit trades C Adam Oates and F Paul MacLean to St. Louis for F Bernie Federko and F Tony McKegney
 
  Adam Oates Oates and Yzerman did get to the finals in 1998 ... but on opposite teams. 
Rick Stewart/Allsport
Remember Game 7 of the 1996 Western Conference semifinals, Detroit vs. St. Louis, a 0-0 tie, goes into the second OT and Steve Yzerman ends it with a 60-foot slapshot? Well, Mitch Albom claimed that it was Yzerman's way of saying, "Adam&nbpsp;Oates for Bernie Federko, my ass!"

Federko was at the end of a Hall of Fame career, while Oates was just finishing his third full season with Detroit. Federko would post 57 points in his only season in Detroit, and McKegney was traded after only 14 games. Oates averaged 114 points over the next five seasons with St. Louis and Boston.

  Ryan Nied, Pittsburgh, Pa.:
GM Jimmy Devellano looked to Steve Yzerman, then only 24, to assume lead responsibility for the team's offensive production. There's certainly no way to detract from Yzerman's value ... but critics were quick to point out that there were not enough threats to complement Yzerman.

 
10 Questions
  • Adam Oates, Jan. 7, 2000 
  •  
    This deal raised many eyebrows around the league and caused Detroit faithful to question the competence of the team's GM. It would be dagger to the heart of Red Wings fans for years to come when Devellano chose to cut a controversial deal with divisional rival St. Louis.

    Federko was no slouch, by any means, amassing over 1,100 points with the Blues in 13 seasons. And McKegney had put up respectable numbers with Buffalo early in his career. But these new Red Wings were clearly washed up, and Oates was emerging a substantial offensive force. 


     
    July
    1957 
    Detroit trades Ted Lindsay, G Glenn Hall to Chicago for C Forbes Kennedy, LW Johnny Wilson, G Hank Bassen, and Bill Preston
     
    It's not just the simple fact that the Red Wings gave up two Hall of Famers; it's the plain and simple fact that Detroit owner Jack Adams shipped Lindsay off to Chicago because he was incensed over Lindsay's attempts to form a payer's union.

     
    SI Flashback
  • Stanley Cups '55-59
  • 1995 Stanley Cup
  • 1997 Stanley Cup
  • 1998 Stanley Cup 
  •  
    This trade that broke up the Production Line of Lindsay, Alex Delvecchio and Gordie Howe came two years after back-to-back Cups, and the Wings wouldn't win another until their two-fer in 1997 and 1998.

    "Terrible Ted" would come back to Detroit as a coach and GM, but he never should have been forced to leave in the first place.

    Hall was not only durable, playing an NHL-record 502 consecutive games, he also was still one of the best goalies in the league. After several productive years in Chicago, he took the expansion St. Louis Blues to the NHL finals in 1968 and won the Conn Smythe Trophy. Kennedy, Wilson and Bassen put in some unspectacular time with the Wings, while Preston never played a game.

      Once, they were champions
    Rocky Mountain News -- May 23, 1997
    By Bob Kravitz

    Once, they were champions, a dynasty even, winning four Cups in six years from 1949-50 through 1954-55. The names were a Hockey Hall of Fame roster: Ted Lindsay, Terry Sawchuk, Alec Delvecchio and, of course, Gordie Howe. From the time the franchise began in 1926, when some local businessmen purchased an NHL franchise and stocked it with players from the Western Hockey League's Victoria Cougars, the Cougars / Falcons / Red Wings were among the young league's elite teams.

    But after the 1956-57 season, two years after the last Detroit Cup, the Wings went into a prolonged tailspin.

    There was a series of appalling deals, but the most devastating was the 1957 trade of two legends, Lindsay and goalie Glenn Hall, to Chicago for Hank Bassen, Forbes Kennedy, Bill Preston and [John] Wilson.

    Boston has its Curse of the Bambino.

    The Cleveland Indians have the Curse of Colavito.

    The Red Wings?

    It's the Lindsay Curse. 

     
    July
    1990 
    Detroit selects C Keith Primeau No. 3 overall
     
      Keith Primeau Primeau never quite fit in with the Red Wings. Glenn Cratty/Allsport
    Jaromir Jagr, Darryl Sydor, Derian Hatcher, Keith Tkachuk, Martin Brodeur, Felix Potvin, Doug Weight, Sergei Zubov, and Peter Bondra. All taken after Keith Primeau, a Red Wing whose only redeeming quality was that he was traded for Brendan Shanahan before the 1997 season.

    After being ripped by the fans and media for six miserable years in Detroit, Primeau skipped training camp before the 1996-97 season and requested a trade. It didn't do much to improve his rapport with the fans -- not after he scored but one goal (an empy-netter) in 17 games during the 1996 playoffs.


      The Primeau Blame Game
    The Detroit News -- Sept. 12, 1996
    By Terry Foster

    We must all take responsibility for this failed project called Keith Primeau.

    The fans. The media. The Wings. Keith Primeau. His agent, Don Reynolds.

    Primeau never lived up to our expectations, which right or wrong, is one of the worst sins in professional sports. When a man stumbles after being put on a pedestal, people throw rotten fruits and vegetables with the velocity of Randy Johnson.

    That's what happened here. Primeau, a legitimate nice guy, became a villain because we had one image of him when the Wings drafted him and Primeau gave us another.

    Primeau cannot play for the Red Wings, which means the Wings must trade him if they are to move forward. The man is so stewed mentally, he reminds me of Tim Cheveldae.

    The boos drove Primeau to the edge. The sports talk shows pushed him over the cliff because he never lived up to being drafted third in 1990 -- ahead of Jaromir Jagr. 

     
    June 23
    1975 
    Detroit trades C Marcel Dionne and D Bart Crashley to Los Angeles for D Terry Harper, LW Dan Maloney, and a 2nd-round pick
     
    When Gordie Howe retired in 1971, the Red wings had some talent, including Mickey Redmond, the first Red Wing to score 50 goals in a season. However, they also had a rising young star in Marcel Dionne, the second overall selection in 1971, drafted after Guy LaFleur.

     
    SI Flashback
  • Oct. 20, 1975
  • 10 Questions with Dionne 
  •  
    Dionne had scored 121 points on an awful Red Wings team in 1974-75. He then demanded a raise, sought some sort of free agency; and the Red Wings management sent his rights to Los Angeles for whatever they could get.

    Dionne would go on to have a string of 100-point seasons and retire as the second leading scorer in league history.

    Harper and Maloney would go on to have unspectacular careers in Detroit before being dealt elsewhere.

     
    November 2
    1989 
    Detroit trades F Petr Klima, D Jeff Sharples,
    F Adam Graves and RW Joe Murphy to Edmonton for C Jimmy Carson, RW Kevin McClelland,
    and a 5th-round pick
     
    The Red Wings were on the upswing. They had a young and talented team and they had made the Campbell Conference Finals in 1987 and 1988 after years of being known as the "Dead Wings."

    Jimmy Carson Jimmy Carson grew up in Detroit, but played only two full seasons there. Harry Scull/Allsport  
    But Edmonton, being Edmonton, had downed Detroit in five in both series and the Red Wings were left wondering how they could change things. Then, with the Gretzky trade, the whole dynamic of the Campbell Conference had changed, and the Red Wings management believed they were just a couple of veterans away from returning to Cup glory.

    Along with the Oates trade, this trade got rid of the draft mistakes of the Wings to snag Jimmy Carson, born and raised in Detroit with his grandfather's diner standing in the shadows of the Olympia.

    Klima and Graves became vital parts for Edmonton's 1990 championship team , while Carson would be shipped back to L.A. for Paul Coffey.

    Of course, Coffey would eventually be shipped to Hartford for Brendan Shanahan, proving that even though it may take a while, the Red Wings sometimes get trades right.

      Robert Camilleri, Detroit.:
    The worst had to be the Red Wings trading Petr Klima, Joe Murphy, and Adam Graves for Jimmy Carson. Of course, the Wings had a few whoppers around that time, like Adam Oates for Bernie Federko. 


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