Even though this Original Six team hasn't won as many Cups as Toronto (can you believe that?) they still have plenty to be proud of. Gordie Howe is arguably the greatest hockey player of all time and they got to cheer for him for 24 years. Speaking of 24, that's also how many consecutive playoff appearances they currently have. It's pretty good to be a Red Wing fan, almost makes up for having to live in Detroit (I kid...).
Their pre-cap rosters are frequently referenced when comparing just how ridiculous it used to be pre-2004. While the Ranger$ spent just as much cash, Detroit managed to get the best players and actually win. Yzerman, Fedorov ($28 million for 48 games), Hull, Hasek, Robitaille, Chelios, Lidstrom, etc were too much to deal with. Yzerman spoke of that Cup-run as the one he actually got to enjoy, as he 'knew they would win'.
With the even playing field of the salary cap, they were still blessed with Nicklas Lidstrom and their two newer (now aging) superstars, Datsyuk and Zetterberg. This era is now finally coming to a close, though they're still dangerous.
But throughout their storied history of legendary players, there were still some clunkers. For this list I didn't just grab the 15 players with the least amount of points; that would be boring and too easy. Instead we took a look at players that were disappointing, because that's what sticks with fans. When your team seems poised for greatness but a key player can't hold up their end of the bargain it hurts deep down.
Others that made the list were successful on other teams/leagues, but never found their groove in Motown.
One constant about Detroit management I found interesting is their willingness to buy out contracts and move on from players after one bad season, no matter the pedigree of the player. If it 'aint workin, you're gone! Some of those players went on to have much better careers elsewhere, but it's impossible to say whether it would have ever worked in Detroit. Sometimes it's just a bad fit.
So let's take a look at one of the greatest NHL franchises' top 15 worst players.
15 Keith Primeau
Primeau was drafted at the wrong time. Being taken in 1990 before Jaromir Jagr and Martin Brodeur caused unfair comparisons for most of his career in Detroit. Jagr immediately won two Cups and even scored 62 goals in his sophomore year to rub it in. Brodeur stuck the knife even deeper by taking the Cup from Primeau's Red Wings in 1995.
He just wasn't an early-90s type player. Those few years saw ridiculous goal scoring totals and wide-open hockey. But several years later as the game tightened up he would become a much more valuable contributor.
14 Carlo Colaiacovo
After years of bouncing between the NHL and AHL in Toronto, Colaiacovo finally stuck in St. Louis. As a Blue he provided four solid, but injury-prone years, playing 63, 67, 65, and 64 games.
Detroit signed him for two years, but only used him in six games. In just his second game of the contract, he injured his shoulder and missed most of the year. He didn't play his first home game until April.
With the lockout troubles of 2012-13 and new salary cap worries, Detroit used a valuable compliance buyout on his contract that only had one year remaining at $3.5 million (a little extreme?).
13 Ray Whitney
Ray Whitney's career is an impressive display of longevity, scoring over 1,000 points in his 17 NHL seasons. But Detroit won't make his highlight reel.
After a productive stint in Columbus, playing at nearly a point-per-game pace, he was expected to add some firepower to the Red Wings offense. And while his 43 points in 63 games is decent, it wasn't what they were expecting. His playoff totals of only one goal and three assists were the icing on the crap-cake, and he was gone.
12 Robert Lang
Red Wing fans must have been ecstatic to hear that Lang, the league's leading scorer had been traded to their team. This was the first time in NHL history it had ever happened during the season. To add him to an already stacked lineup of Hull, Zetterberg, Lidstrom, Yzerman, and Shanahan felt like overkill. But the excitement soon faded. Lang played only six games before an injury knocked him out of the lineup. He would return for the playoffs but couldn't prevent elimination.
Without Jagr (his teammate in Pittsburgh and Washington during his best years) his production dropped off sharply. He still scored respectable numbers for a top-six forward but Detroit was expecting a lot more.
11 Luc Robitaille
Surprised to see him here? If you only look at his 30 regular season goals and Stanley Cup win on arguably the greatest roster ever assembled it's easy to sweep his deficiencies under the rug.
But even during the Cup run he only contributed four goals in 23 playoff games. Lucky Luc indeed.
He fell off the map completely during the second year of his two-year $9 million contract, scoring just 11 goals for the lowest total of his career. His lack of speed and production had him planted on the fourth line and even earned him a healthy scratch. A great NHL player, but not a great Red Wing.
10 Boyd Deveraux
Here are the first six picks of the 1996 Entry Draft: Worst ever?
1. Chris Phillips
2. Andrei Zyuzin
3. J.P. Dumont
4. Alex Volchenkov
5. Ric Jackman
6. Boyd Deveraux
At the time, Deveraux struggled with the pressure of being drafted in the top 10, but looking back he did relatively well with his Stanley Cup win.
9 Ray Staszak
Way back in 1985, Detroit signed undrafted free agent Ray Staszak to a huge (for the time) five-year deal worth $1.4 million. This got a lot of attention as it set a new record for rookies. Staszak was a Hobey Baker candidate at the time, lighting up college hockey with 72 points in 38 games.
After just four games in which Detroit and Staszak played miserably (lost all four, one assist), he was sent down to the minors to get his confidence back. But while finding his stride on the farm team he injured his groin during practice. Staszak was a proud (and medically ignorant) man. He continued to play through the injury, causing even more damage and eventually ending his career.
8 Bob Essensa
Detroit traded all-star Tim Cheveldae and a feisty young Dallas Drake for Essensa in 1993-94. I'm a longtime Canuck fan so I know him as 'Backup-Bob', the likable, but definitely second-tier journeyman goaltender. At the time of the trade however, he was much more highly regarded.
He had previously won an NCAA Title for Michigan State and in 1991-92 finished third in Vezina voting (behind Roy and Kirk Maclean). Detroit was looking to upgrade their goaltending to finally win a Cup and the local hero Essensa seemed like a great fit.
It didn't work out for Bob however, as he posted a dismal 4-7-1 record to end the season and lost his job to rookie Chris Osgood.
7 Uwe Krupp
Imagine; $16.4 million bought just 32 games over two seasons.
Injuries kept him out of the lineup from the beginning, which is an unfortunate aspect of all professional sports. But it's what he did while 'injured' that really stung.
While too hurt to play, it was discovered that he was apparently healthy enough to go dogsled racing! This obviously caused a massive problem between Krupp and the team.
6 Tim Cheveldae
There's a long history of scapegoating goaltenders in Detroit, Cheveldae and Osgood know this all too well.
Cheveldae was the Marc-Andre Fleury of his time, posting great regular season totals (128-93-30-7) but disappointing playoff numbers (9-15).
5 Red Berenson/Tim Ecclestone
These are the two players Detroit got in return for trading Gary Unger to St. Louis.
Unger went on from that trade to have a stellar career, posting eight consecutive 30-goal seasons and holding the Iron Man streak in the 1970s. Pretty great deal for St. Louis.
How about Detroit? Well, Berenson was decent and Ecclestone did nothing.
The kicker is that Unger was traded - and I'm not making this up - for having long hair. Coach/GM Ned Harkness was running a stern ship and couldn't stand insubordination.
4 Errol Thompson
A few great seasons in Toronto gave high hopes for his time in Detroit, but he could never match his previous highs. Despite that, they still made him captain for the disastrous 1980-81 season, in which they won a pitiful 19 games.
Captain Thompson was traded before the train-wreck campaign was over and he would retire after 34 games with Pittsburgh.
3 Brad Norton
The skilled Red Wings were tired of getting pushed around and went after an enforcer. Norton was their man and he even switched from defense to forward for the job.
It was expected that he couldn't score, but surprising that he couldn't fight either! Norton failed to make a mark and was gone after only six games (reoccurring number).
Not sure what Detroit was expecting as his previous high for games played was 53 with LA in 2002-03, and he only played seven for Ottawa in 2005-06.
2 Derian Hatcher
In the late 90s, the Dallas Hatcher was a beast. A big, snarly defender who was completely within the rules to bearhug you MMA style. His championship pedigree and past performance earned him a very nice five-year contract with Detroit, worth $30 million in 2003.
Hatcher would only last a few games however before injuring his ACL for most of the season. He was already slow before the injury, and he got even slower.
The lockout came next and Detroit showed incredible foresight to buy him out. The combination of a salary cap and faster game greatly reduced his effectiveness.
1 Sean Avery
Avery first came along when 'agitators' were more sought after. The days of super-pests like Esa Tikkanen and Claude Lemieux gave valuable meaning to the name. These were players that opposing players hated to play, but their teammates loved having on their side.
No side liked Avery.
He managed to find a way out of every locker room and leave a black mark on the sport with his ridiculous antics. His disgusting show of unsportsmanship in front of Broduer prompted a rule change (as if they really need to have that in writing!) and his desperate attention-seeking comments to reporters were embarrassing to the league. Good riddance.
While a rookie in Detroit he was taught a valuable lesson from teammate Brett Hull. The Red Wings were playing the rival Avalanche and a face-off was taking place near the player benches. Joe Sakic was lining up for the draw and Avery stood up to start talking trash from the bench to the Hall-of-Famer. Hull grabbed Avery and yanked him down saying "You, do not get to talk to Mr. Sakic".
It's incredible to hear stories of such class in the face of such an ass.
Thank you Hull.
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