For the last 15 years, Ken Holland has been regarded as arguably the best general manager in all of sports.
Holland was hired by the Red Wings in 1990 as a professional scout, and after the organization's 1997 Stanley Cup win, Holland was made the general manager.
Since that time, Holland has led Detroit to three more Stanley Cups as well as ten division titles.
Ken Holland has been the mastermind behind numerous free agent signings and trades during his time as the Detroit Red Wings general manager. These deals have kept the Red Wings in contention, and Holland looks to make future deals to keep the Red Wings in contention.
With nearly $6 million in cap space the Red Wings look to be making a deal to improve the team this season, so with that said let's look back at the biggest deadline deals of Ken Holland's career.
Many people might overlook this, but the Todd Bertuzzi deal was bigger than you think.
He played eight games with the Red Wings, as well as 16 playoff games.
Not much time to make an impact, but Bertuzzi did come back to the Wings two years later, and has made those two years count with 40+ point seasons in both. He's on his way to a third with the Red Wings this year.
If Bertuzzi hadn't spent that short time with the Red Wings' organization, who knows if he would've came back in 2009.
The Red Wings sent prospect Shawn Matthias and a conditional draft pick to the Florida Panthers for Bertuzzi. Matthias only has 53 points in his NHL career, while the draft pick, Nick Spaling, only has 32 points.
Not a bad deal for the Wings' overall. Not the best by Ken Holland, but not nearly the worst.
Mathieu Schneider was acquired by the Red Wings in the 2003 Trade Deadline. Schneider played with the Red Wings for four seasons and he had 50+ point seasons in two of them.
Not a bad deal for what they gave.
In return, the LA Kings got bad apple Sean Avery, Maxim Kuznetsov, their first round pick in 2003, and their second round pick in 2004.
Those who pay even just a little bit of attention to NHL news know of Sean Avery. His biggest impact in the league has been to have a rule made in his honor.
Although Avery has been a good player at times, his attitude is still a huge turnoff for teams, and Ken Holland was happy just to be rid of him. In his words:
"The only thing I would say is obviously we had him as a young player at that time and our concern was his lack of respect for the game, the people in the game and, obviously, he left us. He has worked his way through a few organizations now and it's apparent that he hasn't matured." - Ken Holland
Kuznetsov only managed to put up 10 points in his NHL career. The first round pick in 2003 was Jeff Tambellini, who only has 63 points in his NHL career, and the second round pick in 2004, Martins Karsums, has only played 24 NHL games.
Not a bad trade-off all things considered.
Ken Holland managed to pick up Brad Stuart during the 2008 trade deadline. Anybody who's been watching hockey for the last five years knows how far the Red Wings went in 2008.
Since that time, Stuart has consistently been one of the best shot blockers as well as one of the best hitters for the Detroit Red Wings.
He didn't come at a bad price either. Detroit sent the LA Kings their 2008 second round pick, and their 2009 fourth round pick.
With the second round pick, the Kings acquired Peter Delmas, who is a long shot to make the NHL.
With their fourth round pick, the Kings selected Ben Chiarot, who is also unlikely to make the NHL.
Not a bad deal for the Red Wings, even if Stuart is likely to leave after his contract with the team ends.
Acquiring Robert Lang was certainly one of the biggest deadline acquisitions by Ken Holland for the Detroit Red Wings. Unfortunately, this big acquisition wasn't a good one.
Certainly Lang wasn't a bad player, but what the Red Wings got out of it wasn't a good trade-off.
Lang put up 119 points in 159 games during his time with Detroit. Those are great numbers. Unfortunately, the Red Wings traded away Tomas Fleischmann, their first round pick in 2004, and a fourth round pick in 2006.
The Washington Capitals didn't get much out of the fourth round pick, as Luke Lynes has never played a game in the NHL.
Fleischmann is a bit of a bigger deal though, as he has 193 points in 352 games. This season Fleischmann is on pace for nearly 60 points with the Florida Panthers.
That's not the worst of the trade though, the first round pick the Capitals received turned out to be All-Star defenseman and two time Norris Trophy nominee Mike Green.
And you don't need numbers to know that Green worth more than Robert Lang.
Chris Chelios is easily the biggest deadline deal in Ken Holland's tenure as Red Wings General Manager.
Although Chelios was traded to the Red Wings at the age of 37, he played with the Red Wings for 10 seasons. During that time, Chelios racked up 152 points and had a plus-158 rating with the Red Wings.
During the years he spent with Detroit, the Hockey Hall of Famer continued his legacy as one of the greatest U.S. Born defenders in NHL history.
The Red Wings acquired Chelios by giving away Anders Eriksson and their 1999 First Round Draft Pick, with which Chicago chose Steve McCarthy.
Eriksson only went on to put up 137 points in 421 games with seven different NHL teams.
Steve McCarthy played just 302 NHL games, and during that time he only managed to put up 55 points.
Detroit undoubtedly made off on the better of the Chelios trade, with 10 years of great leadership as well as good defensive presence.
Chelios is now retired but still works with the Detroit Red Wings as Ken Holland's Executive Adviser.