The Top 5 Worst Moves by Ken Holland

Updated: August 22, 2016 at 4:38 pm by Scott Maxwell

Nobody’s perfect, and that’s especially the case with general managers in the world of sports. Hockeytown’s notorious mastermind, Ken Holland, is certainly no exception. While he’s made plenty of good moves in his almost 20 year tenure with the Red Wings, he’s had his fair share of bad one’s as well. So, let’s take a look at his five worst moves in his career.

5. 2001 3rd Round Pick to Nashville for a 2000 4th Round Pick

While this may seem like a nothing trade, there are a couple of levels to this trade that make it a bad one.

First, while you may be thinking it’s just a simple trade down in the draft, it clearly isn’t. Usually when you’re trading down, you get multiple picks, in this case, two fourths, or a fourth and a fifth, something like that. Nope, not here. Holland decided to just swap picks of completely different value. The only perspective I can comprehend is that the Wings had a guy coming up that they really wanted, and were desperate enough to give up a higher pick in the next season.

But, that theory goes away when you find out who they drafted with the fourth. They selected Stefan Liv with that pick, a Polish goalie who spent most of his career in the Swedish Elite League. While he was a solid goalie, playing for team Sweden in the Olympics twice, he never panned out for the Wings, as he played just one season in North America before returning to Europe, and never played for the Wings. Liv joined the KHL in 2010, and unfortunately died as a part of the plane crash with his Lokomotiv teammates.

It gets worse for Detroit. Who was the player selected with the third round pick they traded away? Patrick Sharp. While this is one of those trades that you need hindsight for, and it’s tough to evaluate a draft pick that hadn’t been used at the time of the trade, it still backfired badly for Detroit, so it cracks the top 5.

4. Stephen Weiss Signing (5 years, $24.5 million)

At first, this seemed like a good move for Detroit. Weiss was a solid, 0.5 point per game player throughout his career, although there was some caution, as he was coming off a 17 game, four point season, albeit in the lockout shortened 2013 season. However, that didn’t stop Holland from locking up Weiss long term, giving him a five year contract with a $4.9 AAV.

The contract backfired immediately, as he played just 26 games in 2013-14 before needing hernia surgery to end his season, only putting up four points on the board that year. The following season, he was in the lineup for 52 games, and had a slightly better season, with 25 points. That still wasn’t enough though, as the Red Wings bought out his contract, giving the Wings dead cap space that they really don’t need right now, including a $2.56 million cap hit in 2017-18.

To make matters worse, the Weiss signing was at the expense of resigning Valterri Filppula, who has gone on to be an effective player for the Tampa Bay Lightning.

3. Derian Hatcher Signing (5 years, $30 million)

The captain of the 1999 Stanley Cup champion Dallas Stars, Hatcher looked like a good signing for the Wings, as he was going to help out their blueline. His most recent season with Dallas in 2002-03 saw him put up 30 points.

However, he played just 15 games for the Wings before suffering a torn ACL, and missing the rest of the season. The following season was the lockout year, and his contract was bought out because of the new salary cap. Luckily, it didn’t cause any problems afterward, but the signing had the potential to be so much more than it ended up being.

2. Sebastien Piche and a 2012 1st Round Pick to Tampa Bay for Kyle Quincey

Back in 2012, the Red Wings needed to improve their blueline after the signing of Mike Commodore turned out to not pan out. So, the Red Wings added some depth in a three way trade, acquiring former Wing Kyle Quincey from Tampa Bay, who first acquired him from Colorado.

While Quincey wasn’t terrible for Detroit, he certainly wasn’t great either, especially not for the price that the Red Wings had to pay. Not only was he not what fans anticipated, only hitting as high as 18 points, but he became Holland’s plan B whenever his contract expired. In 2012, Holland wanted Suter, didn’t get him, and settled for Quincey. In 2014, Holland wanted Niskanen or Robidas, didn’t get him, and settled for Quincey. I’m surprised that Holland hasn’t resigned him this offseason as well, considering how Holland has decided to sign enough veterans to make it impossible for the young guys to get any ice time.

The worst part. The 1st round pick turned into Andrei Vasilevskiy, whose considered to be one of the better young goalies in the league. While the first round pick is slightly understandable at that point, since Paul Gaustad was traded for a first as well, but it’s still a high price for a bottom pair defenseman.

1. Uwe Krupp Signing (4 years, $16.4 million)

Like the previous two contracts on this list, the main reason why this signing didn’t pan out was due to injuries. However, despite being the shortest term, and lowest cap hit, there was so much trouble with this deal that it puts it over the top.

Krupp was already a polarizing figure to Wings fans, as he scored the Cup winning goal for the rival Colorado Avalanche in 1996. The contract barely panned out, as he played just 30 games over the four years, with just six points to his name. Not only that, but a scandal broke out that Krupp was dogsled racing when he wasn’t in the lineup, and then sued the team after they suspended him.

The contract wasn’t as bad, but Krupp was so much of a head case for the organization that he climbs to the top spot, even if they won a Cup with him on the team.