San Jose Sharks: Top Five Trades in Team History

The San Jose Sharks have yet to bring home the coveted Stanley Cup during their 17 seasons of existence.

However, it hasn't been for a lack of a quality coaching staffs, nor the lack of quality management.

With an organization that has been filled with great hockey minds from top to bottom throughout its history, the Sharks have boasted some of the most highly-talked about teams since their inception.

First, it was the 1994 first-round upset of the top-seeded Detroit Red Wings, and a year later it was another first-round shocker over the No. 2-seeded Calgary Flames.

Five years later, the Sharks were once again a Cinderella winner when they knocked off the top-seeded St. Louis Blues in the 2000 quarterfinals.

Over the next four seasons the Sharks made the postseason three different times, capped off by a run to the Western Conference Finals during the 2003-04 season.

After the lockout, the Sharks struggled in the first two months of the season before acquiring Joe Thornton in late November. San Jose then went on to finish an impressive fifth place in the Western Conference before being eliminated in the conference semifinals.

Three years later, the Sharks won their first ever President's Trophy as the best team in the regular season.

And while last season's first-round collapse was a major disappointment, there is no denying how impressive they have been over the last 14 seasons.

During that span, the Sharks have qualified for the playoffs 12 different times, including five in a row.

After this season comes to a close, it will be 13 in 15, with six straight appearances.

Postseason failures may linger as the final outcome each season, but most NHL teams aren't nearly as fortunate to make the playoffs as often as San Jose has over the last decade-and-a-half.

Now, what has been able to sustain this tremendous regular-season success when players come and go?

Well, no matter who has been running the franchise, the Sharks have benefited from five of the most noteworthy trades over that span.

In fact, the most recent of the five may go down as the biggest steal of the decade.

Now without further ado, here are the top five trades in Sharks history.

No. 5: Kyle McLaren, Acquired from Boston Bruins (1/23/03)

In a three-way deal, the San Jose Sharks sent Nicklas Sundstrom and a third-round pick to the Montreal Canadiens for goaltender Jeff Hackett. They then proceeded to trade defenseman Jeff Jillson and Hackett to the Boston Bruins for Kyle McLaren and a fourth-round pick.

I thought about putting either the Owen Nolan trade or the Mike Ricci trade in this spot, but both of those trades were pretty equal. The Sharks had to give up Sandis Ozolinsh for Nolan, and in order to get Ricci, the Sharks traded Shean Donovan and a first-round draft choice that ended up becoming Alex Tanguay.

Therefore, I have decided to choose McLaren's arrival as the fifth-best trade in team history because they essentially gave up nothing.

Sundstrom went on to tally just 30 points over parts of three seasons with the Canadiens.

Jeff Jillson ended up washing out of the NHL quicker than you can say hamburger, and Jeff Hackett won just 18 games after the trade in parts of two seasons with the Bruins and Flyers before calling it quits.

But Kyle McLaren became one of the Western Conference's most feared defenseman during his tenure with the Sharks.

The 6'4", 235-pound beast of a defenseman dished out punishing hit after hit during four-and-a-half seasons with the Sharks, which included four postseason appearances for Team Teal.

McLaren was without a doubt one of the main reasons San Jose was able to reach the conference finals back in 2003-04. The physical play McLaren brought to the defense enabled the Sharks to withstand the grueling grind of the postseason.

No. 4: Vincent Damphousse, Acquired from Montreal Canadiens (3/23/99)

Former Sharks GM Dean Lombardi pulled off an absolute steal at the trade deadline during the 1998-99 NHL season.

In order to gear up for the postseason, Lombardi sent a fifth-round draft choice from 1999, a second round draft choice from 2000, and future considerations to the Montreal Canadiens for playmaking center, Vincent Damphousse.

"Vinny", as he is known, may have been on the downside of a Hall of Fame career, but he still had plenty of gas left in the tank.

Upon arriving in San Jose, Damphousse tallied 13 points in his first 12 games to finish out the regular season.

In six playoff games, Damphousse continued to be a force, picking up five points before the Sharks were eliminated by Dallas.

The following season saw the Quebec native post an impressive 70 points in his first full season with the Sharks and helped lead them to a first-round upset of the top-seeded St. Louis Blues.

While Damphousse wouldn't match that mark for the remainder of his career, he still provided a veteran presence and playmaking ability that was second to none on the Sharks of the early 2000s.

Despite finishing with just 41 points in the regular season of the 2003-04 campaign, Damphousse was the catalyst for the biggest regular season comeback in team history.

Down 3-1 in the last 22 seconds of the regular season finale against the Los Angeles Kings, the Sharks scored two goals to tie up the game and force overtime. The tying goal was set up beautifully by Damphousse, who would also score the game-winner in overtime.

While the game may have been meaningless in the standings, the momentum gained helped the team and Damphousse make an incredible run to San Jose's first ever Western Conference Finals appearance.

In 17 playoff games that year, Damphousse tallied an impressive 14 points in what ended up being his final season.

Without the Damphousse trade, the Sharks of the late 1990s/early 2000s wouldn't have sustained the regular season success that they did during that span.

No. 3: Dan Boyle, Acquired from Tampa Bay Lightning (7/4/08)

After puck-moving defenseman Brian Campbell had run for the money in free agency, GM Doug Wilson decided to trade for a better puck-moving defenseman in the summer of 2008.

Just a few days after the free agency period had begun, the Sharks traded away defenseman Matt Carle, prospect Ty Wishart, and a first and fourth-round draft choice to the Tampa Bay Lightning in exchange for defenseman Dan Boyle and Brad Lukowich.

Carle has turned out to be a decent offensive defenseman now with Philadelphia, but Wishart has yet to live up to expectations, and neither draft choice is likely to establish themselves as anything more than a role player.

And while Lukowich is no longer with San Jose, the main cog in this deal is Dan Boyle.

A member of Team Canada, Boyle is arguably the best puck-moving defenseman in the entire Western Conference. Since the trade, Boyle has tallied 114 points in 137 games.

With Canada in the Olympics, Boyle was able to win a gold medal to go along with the Stanley Cup ring he earned with Tampa Bay back in 2003-04.

As a true No. 1 defenseman, Boyle is in the top five in almost every defensive category, and is the heart and soul of this Sharks team.

His work ethic and pride are second to none in this league, and if he were to go down with an injury—knock on wood—the Sharks would essentially kiss their Cup dreams goodbye.

As the quarterback on the power play and averaging over 26 minutes a game, Boyle means more to this team than anyone else.

No. 2: Joe Thornton, Acquired from Boston Bruins (11/30/05)

Yes, this deal isn't No. 1 on the list. While the Sharks did essentially "steal" Joe Thornton from the Boston Bruins back in 2005, the three players that were sent the other way aren't exactly "chicken scratch," as some fans like to think.

Granted, center Wayne Primeau has tallied just 57 points in 246 games for three different teams since the trade, but defenseman Brad Stuart and forward Marco Sturm are quality players.

Stuart was traded out of Boston two years later but has found a nice home in Detroit, winning a cup with the Red Wings back in 2008. While he may not score very often, he is quite the underrated defenseman.

Sturm is the only one of the three who has remained in Boston long-term, but he is quite a solid scorer, averaging .66 points per game in 286 contests for the Bruins.

That said, Joe Thornton has been an absolutely dominant force since coming over to San Jose.

Thornton won both the Art Ross Trophy for most points and the Hart Trophy as MVP of the league during the year he was traded.

That year, Thornton finished with an amazing 125 points. However, his play has arguably declined every year since.

In his first full season with the Sharks Thornton's point total fell to 114, then to 96 two years ago, and 86 last season.

Fortunately, that trend will be broken this year as Thornton is already at 79 points with 16 games to go.

But part of the reason the Thornton trade is No. 2 on the list, and not No. 1, is because of the catalyst to which Jumbo will break his string of declining point totals.

That catalyst is a first-year teammate whose name can be found in the title of the following slide.

No. 1: Dany Heatley, Acquired from Ottawa Senators (9/12/09)

The biggest steal of the decade is none other than the Dany Heatley trade. In mid-September, the Sharks acquired the star sniper along with a fifth-round draft choice from Ottawa in exchange for wingers Milan Michalek and Jonathan Cheechoo, and a second-round draft choice.

Through the first 66 games as a Shark, Heatley has tallied 36 goals and 36 assists for 72 points.

Michalek and Cheechoo, on the other hand, have combined for just 27 goals and 19 assists for 46 points between them in 61 games each.

In fact, Cheechoo is now playing for Ottawa's minor league affiliate in the AHL.

This deal was an absolute robbery.

Now, it is true that I wrote earlier in the year about how this deal wasn't as one-sided as it initially appeared.

However, the fact that Cheechoo's career is seemingly over and that Michalek is on pace for his worst season since his first year in the league demonstrates how big of a theft this trade really was.

Heatley's 72 points are 26 more than the combined totals of Michalek and Cheechoo, and the Heater is playing for a team that has legitimate Stanley Cup aspirations.

Neither Michalek or Cheechoo has raised his game come the postseason, but Heatley has shown the ability to perform at the highest level in the postseason.

It is his ability to be a star when it matters most that gives this year's Sharks team the best chance to get over the hump and win the Cup compared to any other team in history.

While last year's squad may have proved to be deeper defensively, Heatley's acquisition for this year's team will more than make up for that loss come the postseason.

Why does the Heatley deal come ahead of the Thornton deal on the list?

Two reasons:

1. Ottawa received less talent in return in the Heatley deal than Boston received in the Thornton trade.

2. Great players make other players better, and this year, Heatley has made Thornton better, not the other way around.

Because of this, the acquisition of Dany Heatley is the biggest steal of the decade, and the top trade in franchise history.