Ex-Detroit Red Wings GM Ken Holland’s best free-agent signings – Honorable Mentions

As we count down former Detroit Red Wings general manager Ken Holland‘s best free-agent signings, there are naturally a few that worked out for the best but didn’t quite qualify for a space in the top five list.

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Let’s take a look back at some honorable mentions that made some significant contributions to the Red Wings over the years.

Steve Duchesne

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Veteran defenseman Steve Duchesne was brought aboard by the Red Wings following the 1998-99 Season, and he proceeded to play three years in the Motor City. He was among a handful of players who won their first Stanley Cup as part of the legendary 2002 squad. He then called it a career.

Chris Osgood

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“Ozzie” was the odd man out when the Red Wings acquired Dominik Hasek in the summer of 2001, eventually heading to the New York Islanders via waivers. He helped New York to a playoff spot in his first year with the team, but would eventually be traded to Detroit’s Central Division rival St. Louis Blues in 2003.

After 1 1/2 seasons with the Blues, Osgood was brought back by the Red Wings prior to the 2005-06 season on a one-year contract. He formed a good 1-2 punch with Manny Legace as the Red Wings cruised their way through the regular season. After Legace was cut loose, Detroit once again brought in Dominik Hasek, who remained Detroit’s starter for much of the regular season and in the playoffs.

But it was in 2008 where things really came full circle. Osgood played well enough during the 2007-08 season to earn an All-Star appearance, though the team decided to start Hasek for the 2008 Stanley Cup Playoffs. It wasn’t long before Osgood found himself back in the crease, replacing Hasek during Game 4 of the opening round series against the Nashville Predators. Osgood remained the starter for Detroit as they powered their way to the 2008 Stanley Cup title.

Osgood then re-gained form for the 2009 Stanley Cup Playoffs after struggling for most of the regular season. He’d spend two more years in Detroit, mostly playing behind Jimmy Howard. He also earned his 400th career victory in December of 2010 before calling it a career in 2011.

Dan Cleary

Known mostly as a grinding and penalty killing forward, Dan Cleary once again played that role with the Red Wings after earning a contract following his invitation to training camp in 2005.

However, he’d soon find himself as chipping in key goals the following regular season and playoffs. He became the first NHL player from Newfoundland and Labrador, Canada to win the Stanley Cup in 2008. He also scored key goals for Detroit the following playoff run, including the winning tally against the Ducks in Game 7 of the Western Conference Semi-Finals.