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

The Hockey Writers

Throughout the years, every organization has made signings that years later are viewed as either underrated or really good moves in hindsight. The Detroit Red Wings are no different, having made a handful of free-agent signings throughout the past 20 years that have been viewed in this way.

Daniel Cleary – 2005

Originally a first-round pick by the Chicago Blackhawks in the 1997 Draft, Dan Clearly was traded to the Edmonton Oilers before making a move to the NHL. He spent time in Edmonton until he was bought out in 2003 and then played in Sweden during the NHL lockout of 2004-05.

In 2005, the Red Wings invited Cleary to training camp and he performed well enough to be given a one-year contract that was worth $450,000. During his first season with Detroit, he quickly earned a reputation as a very good defensive forward, which led to him being given a more prominent role in the lineup in the 2006-07 season.

In the 2006-07 season, on top of being a top defensive forward, Cleary added a little more flair to the offensive side of his game. He put up his first of three seasons of 20 or more goals with the Red Wings, doing so in the 2007-08 and 2010-11 seasons as well. After another impressive regular season with the Red Wings in the 2007-08 season, Cleary earned himself a four-year extension worth $14 million.

The 2008-09 season was when Cleary was able to finally prove his impact in the playoffs. After a down season scoring-wise in the regular season (14 goals in 74 games), he was able to put up nine goals, six assists, and 15 total points in the playoffs while helping the Red Wings win their first Stanley Cup since the 2001-02 season. In doing so, he became the first Newfoundland-born player to win a Stanley Cup. In his playoff career with Detroit, he tallied 23 goals, 27 assists, and 50 points in 111 games.

Dan Cleary
Detroit Red Wing Daniel Cleary – Photo By: Andy Martin Jr

Cleary’s best regular season numbers came in the 2010-11 season, where he tallied 26 goals (career-high), 20 assists, and 46 total points (career-high). Throughout his time in Detroit, he collected a total of 124 goals, 151 assists, and 275 points in 609 regular season games in the Winged Wheel jersey.

Though his numbers may not jump off the screen, Cleary was a vital part of the Red Wings’ success in the late 2000s on and off the ice, being a mentor for younger players in the locker room. He has also stuck around the organization, taking on the role of Director of Player Development. Not bad for a guy who earned his way onto the team as a training camp invite and was able to turn it into a ten-year career in Detroit.

Chris Osgood – 2005

Another player the Red Wings brought in for the 2005-06 season was the return of goaltender Chris Osgood. In his first stint with Detroit, he helped lead the Red Wings to two Stanley Cups in the 1996-97 and 1997-98 seasons. But after the team acquired Dominik Hasek in 2001, he was placed on waivers and claimed by the New York Islanders. Osgood spent parts of two seasons in New York before being traded to the St. Louis Blues in 2003.

In August 2005 Osgood returned to Detroit on a one-year deal in free agency. The 2005-06 season did not go as planned though, being riddled with injuries throughout the year. He did re-sign with the organization in the offseason though on a two-year deal. But the team also brought back Hasek in the offseason as well and the plan was for them to be a goaltending tandem for the season. But like the 2005-06 season, 2006-07 was another injury-riddled year for Osgood.

Chris Osgood Detroit Red Wings
Chris Osgood, Detroit Red Wings (Photo by Claus Andersen/Getty Images)

It was not until the 2007-08 season that Osgood returned to his true form, which boded well for the Red Wings. He was able to turn his injury luck around and reclaim his number-one spot in net while Hasek was injured throughout the season. This led to Osgood putting up a 27-9-4 record with a league-leading 2.09 goals-against average (GAA) and a .914 save percentage after the month of April. He also earned himself an All-Star appearance, along with a three-year extension with the team for his efforts.

Related: The Rest Is Red Wings History: Osgood Replaces Hasek and Wins 2008 Stanley Cup

But when Hasek was back and healthy, head coach Mike Babcock chose to alternate between the two goaltenders and rode Hasek in the playoffs. This was until Game 4 of the first round when Osgood replaced Hasek in net and never gave it back. Throughout the Red Wings’ run to a Stanley Cup victory, he was able to compile a 14-4 record, with a stellar 1.55 GAA, and was vital in helping the team win the Cup.


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The following season, Osgood’s regular season failed to meet the numbers he put up the previous year, but was again relied on in the playoffs, putting up a 15-8 record and a 2.01 GAA. He was viewed as a leading candidate for the Conn Smythe if the Red Wings had been able to win the Cup again, but they fell short in seven games in a rematch with the Pittsburgh Penguins.

Although he was inconsistent in his return to Detroit, Osgood played a vital part in the Red Wings making back-to-back Stanley Cup Final appearances and played an important role like Cleary in being a mentor for younger players in the locker room.

Brian Rafalski – 2007

The first player on this list that was signed to a multi-year deal, Brian Rafalski came to the Red Wings after spending the first seven seasons of his NHL career with the New Jersey Devils. With the Devils, he won two Stanley Cups (2000, 2003) and was viewed as a top-pair defenseman at the time of signing with Detroit in 2007.

When he arrived in Detroit, Rafalski immediately joined Nick Lidstrom on the Red Wings’ top defensive pairing and created one of the best duos in the entire league. In his first year in Detroit, he set a career-high in goals with 13 and played a vital role on a power play that ranked third in the NHL. He totaled 10 power play goals during the 2007-08 season, which tied for the league lead for defensemen. In the four seasons he spent with the Red Wings, he totaled 20 goals, 75 assists, and 95 points on the power play.

Brian Rafalski Detroit Red Wings
Brian Rafalski, Detroit Red Wings (Photo By Dave Sandford/Getty Images)

Rafalski also played a vital role for the team on their way to a Stanley Cup victory in 2007-08 and their run to the Final again in 2008-09. During his time in Detroit, he was able to suit up in 63 playoff games, totaling 12 goals, and 28 assists for 40 points while also compiling a plus/minus of plus-20 in those games. By the end of his career, he had played the most playoff games by a defenseman in the 2000s.

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In the regular season, he was able to suit up in 292 games for the Red Wings, putting up 35 goals, and 169 assists for a total of 204 points, and an impressive plus-78.

Overall, these signings helped the Red Wings stay contenders in the NHL while also making back-to-back Stanley Cup Final appearances and winning one of them.

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