Red Wings’ Worst Free Agent Signings of the Past 20 Years

The Hockey Writers

While there are always bright spots when it comes to free-agent signings, the flip side is the signings that do not pan out as well. Over the past 20 years, the Detroit Red Wings are no exception to this situation.

Derian Hatcher – 2003

Derian Hatcher came to Detroit trying to make his homecoming a feel-good story. It ended up as one of the worst free-agent signings by the Red Wings. Before coming to Detroit on a five-year, $30 million contract, the big-bodied defenseman played his entire 11-year career with the Dallas Stars. While in Dallas, he became the first American-born captain to win a Stanley Cup in 1999 and tallied 71 goals and 223 assists for a total of 294 points in 827 games. He was most known as a physical presence on the back end and totaled 1,380 penalty minutes in Dallas.

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When Hatcher arrived in Detroit, the thought was that he could be that same type of player for the Red Wings. But he only played a total of 15 games after being injured three games into the 2003-04 season. He totaled only four assists in the regular season and one assist in 12 playoff games in a Winged Wheel jersey.

Derian Hatcher Detroit Red Wings
Derian Hatcher, Detroit Red Wings (Photo by Elsa/Getty Images)

When the lockout in 2004 changed the NHL to a salary-cap league, the Red Wings decided to buy out his contract to be compliant with the salary cap. Hatcher played three more seasons with the Philadelphia Flyers before retiring from the NHL in 2009.

Stephen Weiss – 2013

Stephen Weiss signed with the Red Wings in July 2013 after playing eight seasons with the Florida Panthers. The five-year contract then-general manager Ken Holland gave Weiss came as a surprise to some seeing as he had just come off a season where he played only 17 games due to a wrist injury and totaled four points.

Related: Red Wings’ Best Free Agent Signings of the Past 20 Years


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He did, however, have four solid seasons prior to the injury-riddled 2012-13 season, totaling 83 goals, 144 assists and 227 points combined in those four seasons. This is the player that Detroit hoped they were getting in Weiss, but he only lasted two seasons with the Red Wings organization.

Detroit Red Wings center Stephen Weiss (Photo Credit: Andy Martin Jr)

In his first season in Detroit, Weiss played in only 26 games due to hernia surgery and totaled four points. The following season, he split time in Detroit and Grand Rapids. He played in a total of 55 games and tallied only 25 points. He was then bought out by the organization after the 2014-15 season with three years left on his contract.

Frans Nielsen – 2016

Another signing that Holland made in his time in Detroit that did not work out as planned is the Frans Nielsen contract of 2016. He came to Detroit after he spent his first 10 seasons with the New York Islanders. The first year of the six-year deal for him worked out great, with him making the 2017 All-Star Game and totaling 41 points on the season. But, things went downhill from there for the Red Wings and Nielsen.

Frans Nielsen Red Wings
Frans Nielsen, Detroit Red Wings, December 20, 2017 (Amy Irvin / The Hockey Writers)

In the seasons following the 2016-17 campaign, he totaled only 83 points in 240 games for the team and was a minus-41 while on the ice. Over time, fans began to sour on Nielsen and management decided to cut ties with him after the 2020-21 season with one year left on his contract.

Between these three players, they played a combined seven of the 16 contracted years that were given out to them. They have been viewed in the minds of many as some of the worst contracts signed by the organization in the past 20 years for as underwhelming the results were with them.


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