Igor Larianov For Ray Sheppard

What a magical season the 1993-1994 season was for the Sharks, who set a NHL record with a 58-point improvement from the year before. Igor Larianov and Sergei Makarov along with the young Sandis Ozolinsh would be part of a Russian revolution in San Jose.
Backstopped by the great Arturs Irbe with timely offense from the Russian top line, the Sharks would upend the top-seeded Detroit Red Wings in the first round.
Sharks’ hockey had to wait until January 15th, 1995 to resume due to the NHL lockout.
Upon their return, the Sharks struggled to regain the magic from the 1993-1994 season. The Sharks would again play the role of underdog, sending the Calgary Flames packing in seven games.
The Red Wings destroyed the Sharks in the second round, quickly dispatching them while outscoring the Sharks to the tune of 24-6 in the sweep.
A long and sad tale of how the Sharks would unravel would then play out, as one by one our heroes would fall.
Irbe would struggle after being bit by his dog and suffering nerve damage to his glove hand and wrist.
Makarov couldn’t make it out of training camp after reporting out of shape and not ready to play.
Ozolinsh was traded to Colorado after a contract dispute had him play a few games for the now defunct IHL San Francisco Spiders.
Worst of all, Larianov made his way into the doghouse after a run-in with fiery head coach Kevin Constantine in training camp. He was traded on October 24th, a sad day indeed for Sharks fans.
While Sheppard enjoyed some success as a Shark, but he was largely a one-dimensional player and was traded to Florida the following year.
The rebuilding would commence with Constantine and Chuck Grillo being dismissed, leading to the Dean Lombardi-era and the forgettable Al Sims.
Larianov joined the “Russian Five” in Detroit and win back-to-back Stanley Cups as well as scoring over 400 more points.
Steve Bernier and First-Round Pick for Brian Campbell
The Sharks approached the trade deadline in 2008 needing another puck-moving defensemen to bolster the breakout and man the power play. Doug Wilson would trade Steve Bernier and a first-round draft pick to Buffalo for Brian Campbell, who would fit the bill for the most part.
At the time of the trade, Campbell ranked seventh among NHL defensemen with 43 points (5 goals, 38 assists) in 62 games.
While the local media made much of the sexy trade at the deadline and what it brought to the team, many fans worried about the price of the rental. Much was made about Soupy’s childhood relationship with Joe Thornton and the Ottawa 67 connection with GM Wilson, leading to speculation that he would resign.
Campbell played decently, scoring three goals with 16 assists in 20 games down the stretch leading into the playoffs. He would also score the game-tying goal in the third period of the elimination game against the Dallas Stars in the conference semifinals.
Despite those contributions, he didn’t make the difference many fans envisioned and his decision to leave San Jose put him in the fan doghouse.
Despite some poor defensive coverage in the playoffs, Campbell also posted a plus-3 during that time.
Bill Guerin For Ville Nieminen, Jay Barriball and First-Round Pick

Doug Wilson played mad scientist and get burned in this classic tale of locker room chemistry gone awry. Looking for the power forward type of player who could crash the net and contribute along the boards, Wilson would trade for Bill Guerin on February 27, 2007.
Guerin was just 20 days removed from playing his 1,000th NHL game as a member of the St. Louis Blues.
Reunited with Doug Weight in the Gateway City, Guerin had resurrected his career and was a hot commodity at the deadline, initially making Wilson look like a genius.
A gritty, veteran power forward who could score in clutch situations, Guerin was supposed to help lead the Sharks in the playoffs. Instead his critical voice in the locker room would alienate himself from many Sharks and he would turn out to be the worst rental player to ever don the teal.
Who can forget the Game 4 gaffe against the Red Wings when the Sharks were poised to take the 3-1 series lead with just under a minute remaining. Guerin would get caught cheating up ice looking for the empty-net goal, and the Red Wings would even the score with just 30 seconds left.
Guerin would suffer a deep laceration to the face when he was struck by a Christian Ehrhoff slapshot in the following overtime.
Guerin would record just two points in nine playoff games before missing the rest of the postseason with the injury. He’s arguably the worst rental player trade in San Jose Shark history.
Ed Belfour For Chris Terreri, Michal Sykora, and Ulf Dahlen

Ed Belfour was one of the most intense and razor-sharp focused goalies in the NHL.
He went undrafted despite winning a college championship at North Dakota with a tremendous senior season. He went on to be signed as a free agent by the Chicago Blackhawks and in his rookie season he won 44 games in 74 starts and recorded four shutouts with a GAA of 2.47.
Awarded the Calder, Vezina and Jennings trophies that year, he was also nominated for the Hart as the NHL MVP.
Dean Lombardi would trade Chris Terreri, Michal Sykora, and Ulf Dahlen halfway through the 1996-1997 season for Belfour’s services.
The thinking was Belfour would give the Sharks their true bona fide goaltending star, and instead failed to live up to his hype. Crazy Eddie was absolutely horrible with a .884 save percentage and a 3.41 goals against in just 13 games.
There were more than a few whispers in regards to Belfour’s mysterious back injury and why it took so long for him to return.
Despite our team attempting to re-up the goaltender, he strung San Jose along just long enough for him to sign with the Stars the first minute that free agency opened.
Belfour deserved every bit of the venom that would spew forth from the Sharks fanbase, and if he isn’t the most hated ex-Shark, I just don’t know who is.
Owen Nolan For Alyn McCauley, Brad Boyes and a 1st-Round Pick

Yet another transitional period for the Sharks brings us this list’s worst trade in franchise history.
The team struggled mightily in 2002-2003 and would miss the playoffs despite a roster laden with offensive talents.
Darryl Sutter was fired on December 1st during a disappointing season due to Brad Stuart and Evgeni Nabokov contract disputes. The Sharks would have a record of just 8-12-2-2 through 24 games when Sutter was fired, and Ron Wilson was hired to lead the turnaround.
Teemu Selanne, Marco Sturm and Patrick Marleau would score 28 goals apiece and Vincent Damphousse would lead the team with 38 assists. Even with those combined contributions, it was clear that locker room chemistry had failed, and captain Owen Nolan was moved.
On March 5, 2003, the Sharks traded Nolan to the Toronto Maple Leafs for Alyn McCauley, Brad Boyes and a first-round draft choice in 2003.
It was one of the darkest days for Sharks fans as the singular face of the franchise and captain who held so many team records was gone. Dean Lombardi was dismissed just three days later and Doug Wilson would take the reins.
Now, many of you may say that McCauley provided a good return, and he did for the most part.
In 2003-2004, McCauley would have a good year posting 47 points in 82 games and another three points in 11 playoff games.
Boyes has become a much better player than he was during his time in San Jose. He was traded to Boston in a three-way deal that brought Curtis Brown to the Sharks. The first-round pick would be used to select Steve Bernier taken 16th overall.
Some names still on the board when Bernier was taken? Zach Parise, Ryan Getzlaf, Brent Burns, Ryan Kesler, Corey Perry and Mike Richards. Yeah…
So was the return sufficient? Yes, on paper it was quite sufficient, but yet this trade was the one that will always stick in my mind as the worst in Shark history.
Nolan’s leadership, competitive fire and locker room presence were unmatched and to this day not found on the Sharks roster. I can remember when Owen was actually criticized for being too much of a fiery leader in the locker room.
Nolan was a fan favorite as soon as he arrived from Colorado/Quebec in the Ozolinsh trade. San Jose loved Nolan and he would take the reins of leadership without complaining about it.
After Kevin Constatine was shown the door in 1995-1996, and interim coach Jim Wiley could do no better, Owen was consistently the brightest light for the Sharks. Sharks fans loved Nolan despite the team finishing only ahead of lowly Ottawa with a 20-55-7 record.
The Sharks would sell out all 41 home games that season, a testament to the fans in San Jose and Northern California.
Nolan, even with all of his warts and coach-killer label, was and still is the face of the San Jose Sharks to many fans including this one.
Go Sharks