The ability to make a good trade is one of the biggest characteristics of a quality General Manager.
Ken Holland has been in the enviable position of trading from a position of strength. Being a perennial contender means that Detroit has constantly been on the lookout for NHL-ready players who will help the team win a Stanley Cup. The flip side to that is the Wings have consistently traded with teams who were looking to get rid of expensive veterans in exchange for prospects and/or draft picks as part of a rebuilding phase.
In any trade, there typically is a winner and a loser. The team receiving the players typically has an advantage because of the unproven qualities of the prospects and/or draft picks going the other way. There is also a time element to evaluating who won a trade, because a "winner" can turn out to be a "loser" after a prospect or draft pick turns into a superstar player.
In Detroit, Ken Holland has been on the winning side more often than not. Many of the trades he has made in his tenure as GM of the Wings have worked out well, while very few have been flops. However, he's been able to hit a couple of home runs by fleecing another GM out of a great player while giving up virtually nothing. Let's take a look at the best and worst trades made by the Red Wings in the last 21 years.
BEST: The Brendan Shanahan trade:
When the 1996-97 season began, the Red Wings were coming off the best regular season of any team in the history of the NHL. Unfortunately, that season ended in failure as the Wings were unable to make it past the Western Conference Finals. After 4 straight years of early playoff exits, the Wings were in need of a change.
Enter Brendan Shanahan. Shanny was a star player who had some off-ice....difficulties in St Louis and was sent to Hartford for Chris Pronger. Much like Rick Nash in Columbus, this was a case of a star forward wasting away on a bad hockey team.
The Red Wings needed to get tougher, but they also didn't want to sacrifice the talent level that they had built up in the years previously, so they targeted Shanahan just prior to the season.
What did they give up? A still-effective-but-well-past-his-prime Paul Coffey, an underachiever (to that point) in Keith Primeau, and their 1997 1st round draft pick (which turned into Nikos Tselios, who did nothing in his NHL career).
Coffey bounced from the Whalers to the Flyers (losing to the Wings in the '97 Finals) and then to the Blackhawks, Hurricances and Bruins before calling it a career. He was never the same player after leaving Detroit, failing to break the 40 point plateau in any single season after the trade.
Primeau stayed with the Whalers/Hurricanes for a few years before moving to the Flyers in 2000. He would go on to become their captain and enjoy a successful career in Philadelphia, something that wasn't likely to happen in Detroit given the enormous expectations people had of him when he was drafted.
Shanny? All he did was become a top line player and best power forward on 3 Stanley Cup championship teams. He scored 30 goals in 8 of his 10 seasons in Detroit, and scored important OT goals in 1997 (against Anaheim in the 2nd round) and 1998 (against St Louis in the 2nd round). With Steve Yzerman and Sergei Fedorov, he formed a trio of forwards that was virtually unmatched in the NHL.
Honorable mention: Chris Chelios acquired for literally nothing; Dominik Hasek for Slava Kozlov and a pylon
Picking a "worst" trade for the Red Wings is like asking which Simpsons episode is your least favorite: there aren't a lot to pick from. I thought about going with Kyle Calder for Jason Williams for the sole reason of how worthless Calder was as a Red Wing (and NHL player in general), but Williams never turned out to be anything.
When Robert Lang was traded to Detroit, he was one of the 5 or 6 best players in the NHL (a bit of an indictment of the state of hockey at the time). He was actually the league leader in points at the time of the trade, and the thought was that his presence would take pressure off a team that had lost Fedorov.
Lang would go on to score 62 and 52 points in his 2 full seasons with Detroit, and his first 2 playoff seasons were impressive (9 points in 12 games in 2004 and 6 points against Edmonton in 2006), but in 2007 he potted a paltry 2 goals in 18 games as the Wings were unable to advance to the Finals. He then departed Detroit as a free agent, signing with the Blackhawks.
What did the Wings give up? Fleischmann, a highly-rated prospect who put up very good numbers on a good Washington team (a team that has similar to talent we currently see in Detroit) and similar ones on a less-than-great Florida team but who has dealt with some off-ice health problems that have limited his production, and a 1st round pick that the Caps turned into Mike Green.
You can think what you want about Green as a defensive defenseman, but thinking about what the Wings could have done with his offensive talent while allowing him to learn from Nicklas Lidstrom makes me realize that the Wings might have been better served to keep the pieces they gave up for Lang and used them as part of the future. I think it was one of the few times where I think the Wings would have been better served sticking with their current players and picks and kept an eye on the future rather than go with a "win-at-all-costs" mentality.
Honorable Mention: Calder for Williams; Bertuzzi for Matthias and a pick that turned into Nick Spaling because Bert was useless in his first stint with the Wings; Ville Lei........hahahaha just kidding, Leino sucks.