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    Ex-Detroit Red Wings GM Ken Holland’s worst free-agent signings – No. 1

    Perhaps the most infamous of Ken Holland's free-agent signings in Detroit that didn't turn out as expected.

    We've been counting down former Detroit Red Wings general manager Ken Holland‘s top free-agent signings that didn't work out as expected. In case you missed the first four on the list, let's do a quick recap:

    No. 5 – Carlo Colaiacovo

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    No. 4 – Ray Whitney

    No. 3 – Derian Hatcher

    No. 2 – Stephen Weiss

    And that brings us to number one on our list – defenseman Uwe Krupp.

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    The physically imposing 6'6, 223 lb. German defenseman was signed by the Red Wings in the summer of 1998 to a four year, $16.4 million deal after spending several years with the rival Colorado Avalanche. He even scored Colorado's Stanley Cup winning goal in overtime of Game 4 of the 1996 Stanley Cup Finals against Florida.

    He appeared in only 22 games during the 1998-99 season before a back injury suffered in December of 1999 halted his play. However, the team suspended him without pay when it was discovered that he was racing his dogsled while he was supposed to be rehabbing the injury. Krupp even filed a grievance against the team for the money on his contract before eventually returning to the team for portions of the 2001-02 Stanley Cup winning season.

    Though Krupp raised the Cup at Joe Louis Arena, his name was left off the famed trophy for failing to meet the required time played to achieve the honor.


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