San Jose Sharks: Five Worst Decisions of Doug Wilson's Career

There are few general managers in all of the NHL with more impressive resumes than Doug Wilson.

In seven full seasons with him at the helm, the San Jose Sharks have five division titles and have finished no lower than the fifth seed in the competitive Western Conference. They have three conference finals appearances and have only failed to get out of the first round once.

Only the Detroit Red Wings have a better record over that span and have made the playoffs all seven seasons like the Sharks.

This success cannot be attributed to the players Doug Wilson inherited, as only Patrick Marleau predates Wilson. It cannot be attributed to the coaching staffs, as it has turned over more than one complete staff. There have even been changes to ownership.

The success is because of the shrewd moves Doug Wilson has made.

Trades brought in the top three players currently on the blue line, Marc-Edouard Vlasic, Brent Burns and Dan Boyle. Add in forwards Martin Havlat and captain Joe Thornton and half of the team's eight players with five or more assists came via trade.

While Havlat came in return for Dany Heatley, he had come via trade for Milan Michalek and Jonathan Cheechoo. Thornton cost the team Brad Stuart, Wayne Primeau and Marco Sturm. Boyle's price was Matt Carle, Ty Wishart and a draft pick.

Vlasic's cost was the steepest, but Miikka Kiprusoff was never going to be anything more than a backup to Evgeni Nabokov. Thus, even in hindsight the team would make every trade on that list, though it is too soon to judge the Burns trade until the young talent the Sharks gave up realizes its potential.

He has done reasonably well drafting, with nine players on the roster being his picks and three others being used in the above trades. With his only pick in the top-20 (Logan Couture) being a stud and getting another from as late as the seventh round (Joe Pavelski), there is not enough to say his performance in late June deserves criticism given the inexact science of drafting.

Wilson is also very good at re-signing his own players, getting four of the team's top-six forwards to sign contracts widely regarded as below market value. He has at least one major coup in free agency in each of the last five season: Antti Niemi (2010), Manny Malhotra and Scott Nichol (2009), Rob Blake (2008), Jeremy Roenick (2007) and Mike Grier (2006).

Yet there have been seven other teams to win Lord Stanley's Cup and three more to win the Campbell Trophy as the best in the west over the Sharks. No matter how good you are over seven years, you cannot earn an "A" grade without at least a conference championship.

So where has Wilson gone wrong? Here are five moves that may have impeded a championship, in chronological order.

2005: Extending Kyle McLaren

On August 12, 2005, the San Jose Sharks announced that Kyle McLaren, whose contract was set to expire at the end of the season, had been signed to a three-year, $7.5 million extension.

In the season that followed (the last under the old contract), this appeared to be a shrewd move. McLaren, a stay-at-home defenceman, had two goals and 21 assists with a plus-13 rating in 77 games that season, and followed it up with a three assist, plus-two 11-game playoff performance.

However, in the first two years of the contract, he played in 128 games and scored eight goals and 20 assists total. While he had a plus-13 rating, he was minus-four in the playoffs with four assists in 16 games.

By October of 2008, Doug Wilson essentially acknowledged the McLaren signing was a mistake by waiving him. When no other team wanted to pick up the final year of his contract, the team paid him $2.5 million to sit in the minors.

Philadelphia offered the Sharks a sixth-round pick at the 2009 trade deadline for him, but he failed their physical and the trade was voided. He never played again in the NHL, and Wilson's inability to dump (as opposed to Jonathan Cheechoo's $3 million per season) or get quality performances (as opposed to Evgeni Nabokov's $5.75 million) for a big salary is the reason this is the one re-signing that appears on this list.

2007: Trading for Bill Guerin

Bill Guerin was just what his new team needed. Giving up just a conditional pick that turned out to be a third-rounder, he provided the grit and front-of-net presence that led to 15 points in 24 playoff games and helped his team win a Stanley Cup.

Unfortunately, that trade was made by the Pittsburgh Penguins two years after the Sharks traded for him. They gave up role-player Ville Nieminen, prospect Jay Barriball and a first-round pick that turned out to be star-in-the-making David Perron for him.

That shows just how close one can go from a great trade to arguably the worst in Wilson's tenure. It was also the first of four bad moves by the GM in a 30-month period.

Guerin had five goals and an assist in 15 of his games with the Sharks, but got a hat trick in the other to make the trade look worthwhile. Unfortunately, he was struggling in the playoffs aside from taking a puck to the face that all but ended his effectiveness, and finished with just two assists in nine games.

While the decision not to re-sign the forward made sense, it also solidified this as a bad trade because it ensured the Sharks would get a total of two playoff points for the talent they surrendered. Guerin missed no more than four games in any of his last three seasons while scoring at least 21 goals in all of them.

2008: Trading for Brian Campbell

Another player who was supposed to bring the Cup to San Jose but helped another team reach that goal was Brian Campbell.

Wilson snagged the big fish at the trade deadline, bringing in Joe Thornton's childhood friend who also happened to be a great skating, puck-moving defenceman that was responsible in his own end. In return, they surrendered Steve Bernier and a first-round pick that turned out to be budding star Tyler Ennis.

Campbell elevated the Sharks play to a record-setting March and a second seed. But like his new teammates, he had a disappointing playoffs and the Sharks won no more games than they had the previous two years without him.

Then he left his new fans and his old friend to be closer to home. Even had he wanted to re-sign in San Jose, he proved to be not worth the heavy contract Chicago offered him, but the Sharks lost way too much for no meaningful return to get him.

At best, it can be said that he allowed the Sharks to see what such a player brought to the ice and may have been a factor in their trade for Dan Boyle. He is a better defenceman on both ends of the ice for less money, making that trade better for the Sharks than Campbell could have been, even with the talent lost in that move. However, Wilson should have known such a player was needed without having to make the extra trade.

2009: Trading for Travis Moen and Kent Huskins

For most of the 2008-09 season, the San Jose Sharks were the best team in the league and on their way to the President's Trophy. But that does not mean there were not deficiencies that warranted a deadline trade (outlined in the link).

Doug Wilson was smart enough to see them and do something about it. He traded away two prospects, Timo Pielmeier at the deep position of goalie and centre Nick Bonino.

In return, he got two players who had championship experience and helped provide grit and depth for both forwards and the blue line. Forward Travis Moen played well as a Shark, providing toughness and penalty-killing, but Kent Huskins was never healthy enough to play.

But the trade did not successfully address several team problems, which led to a first-round loss to their trading partner. Moen was not re-signed, but Huskins was inked to a new deal to play on the team's third line.

Still, Pielmeier played just 40 minutes for Anaheim last season and gave up five goals on 12 shots. Bonino was just called up by the Ducks, but has played just 35 games thus far and scored a goal and an assist. That is not much to give up for over two seasons of veteran service, even of role-players.

However, this trade makes this list for two reasons: It was such a colossal failure for that playoff run, and Huskins was not worth the $1.7 million he was paid because he turned out to be nothing better than a seventh defenceman, and that money could have landed a better player.

2009: Dumping Christian Ehrhoff and Brad Lukowich

In the summer before the 2009-10 season, the San Jose Sharks set out to make room for Dany Heatley. They had to choose between Rob Blake and Christian Ehrhoff for about the same money, and chose to stick with Blake.

While Blake had only one season left and his lack of speed was exposed, one could live with that decision. Even the dumping of Brad Lukowich with Ehrhoff was no big deal given he should be no higher than seventh on a contending team's depth chart.

One can even understand not getting equal return in what was essentially a salary dump. But a trade is never good when it helps your trading partner beat you in the conference finals the next year.

That does not even consider the impact of getting nothing in return: San Jose got defenceman Daniel Rahimi and centre Patrick White.

Rahimi is playing in Europe and shows little to believe he will ever be an impact player in the NHL. White just went to the German Premier League after finishing college last season, but a forward scoring fewer than a point per two games in any season in college will struggle to be a role player in the NHL.

In other words, the return might have been adequate for Lukowich but certainly not for Ehrhoff, even when the team is a motivated seller.