Thursday's blockbuster trade to acquire Erik Karlsson from the Ottawa Senators wasn't the first time San Jose Sharks general manager Doug Wilson has fleeced one of his counterparts. In fact, it's not even the first time this offseason he's schooled Sens GM Pierre Dorion.
The Karlsson deal will be Wilson's best transaction if the five-time All-Star gets the Sharks over the hump and they win the Stanley Cup. Here are five other moves (listed in chronological order) Wilson has made to help turn the Sharks into a juggernaut:
Drafting Joe Pavelski
Wilson took over as Sharks GM in May 2003, and about a month later made arguably the franchise's best draft pick, selecting Joe Pavelski in the seventh round (205th overall).
Pavelski has been one of the NHL's most underrated players since entering the league in 2006-07. On a per 82-game basis, he's averaging 30 goals and 64 points per season, and the 34-year-old has also been reliable on both the power play and penalty kill, with the versatility to play either center or wing.
During the Wilson era, the Sharks have missed the postseason just once. They've traded many first-round picks, but have still managed to draft and develop homegrown talent on a level nearly any team in the league would envy.
The Joe Thornton robbery
Joe Thornton is in the twilight of his career now, so it might be easy to forget that he was the centerpiece of a historically lopsided trade.
On Nov. 30, 2005, Wilson acquired the then 26-year-old Thornton from the Boston Bruins in exchange for Marco Sturm, Brad Stuart, and Wayne Primeau. That's it.
Thornton went on to win the Hart Memorial Trophy and the Art Ross Trophy that season, and he sits second in franchise history with 973 points in 961 games, trailing only Patrick Marleau.
The Brent Burns thievery
At the 2011 draft, Wilson pulled off another blockbuster, trading Charlie Coyle, Devin Setoguchi, and a first-round pick (28th overall, Zack Phillips) to the Minnesota Wild for Brent Burns and a second-round pick.
Burns, who was 26 years old at the time, was a good player, but not a great one yet. After rotating between forward and defense during his first few seasons in the Bay Area, he was permanently moved to defense for the 2014-15 season, and a star emerged. Over the last four seasons, he's averaged 21 goals and 70 points, taking home the Norris Trophy in 2016-17.
Meanwhile, Setoguchi didn't reach 20 goals or 40 points again, Coyle still hasn't established himself as a top-six forward, and Phillips never played in the NHL.
Gambling on Martin Jones
On June 26, 2015, Martin Jones was traded from the Los Angeles Kings, along with Colin Miller and a first-round pick (Jakub Zboril), to the Boston Bruins for Milan Lucic. Four days later, Wilson sent Sean Kuraly and a first-round pick (Trent Frederic) to the Bruins for Jones.
Dealing a prospect and a first-rounder for a 25-year-old goaltender with only 29 NHL starts under his belt was a risky move. But it's become one of Wilson's savviest trades, as Jones has proven to be a capable No. 1 goalie and a clutch performer.
Here's a look at his career playoff numbers:
| GP | W-L | GAA | SV% | SO |
|---|---|---|---|---|
| 42 | 22-18 | 2.07 | .926 | 6 |
Frederic is a good-looking prospect, and Kuraly is a solid depth player. But the Sharks definitely wouldn't have gone to the 2016 Stanley Cup Final without Jones in the crease.
Buying low on Evander Kane
Time will tell if this move turns out to truly be one of Wilson's best, but so far, so good.
At the 2018 trade deadline, Wilson sent prospect Danny O'Regan, a second-round pick, and a conditional fourth-round pick to the Buffalo Sabres for Evander Kane (the second-round pick turned into a first once Kane signed an extension).
Since being selected fourth overall in the 2009 NHL Draft, Kane has shown flashes of brilliance and the ability to become a premier power forward. But a combination of injuries, some off-ice incidents, and playing for poor teams have prevented him from reaching his full potential.
In 17 games with San Jose following the deadline, Kane scored nine goals, then added four more in nine postseason contests. A full season in a winning environment, surrounded by some of the best linemates of his career, could result in a 40-plus-goal campaign if he stays healthy.
Acquiring a talented player at a bargain price has worked out for Wilson in the past. Kane and Karlsson are just the most recent examples.
Honorable mentions: Acquiring Dan Boyle from Tampa Bay, Dany Heatley from Ottawa.
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