Erik Karlsson and the NHL Blockbuster Trades That Didn't Work Out
Two years ago, the Pittsburgh Penguins broke everyone's offseason slumber when they acquired Norris Trophy-winning defenseman Erik Karlsson from the San Jose Sharks in a multi-team trade.
The thought was that adding Karlsson to a team that already had Sidney Crosby, Evgeni Malkin, Jake Guentzel and Kris Letang, they would be a dynamic offensive powerhouse, particularly on the power play, and not just get Pittsburgh back to the playoffs but also make a serious run for another Stanley Cup.
Well, it sounded like a fun idea at least.
Sometimes great trades on paper with big stars involved don't work out. We love trades, especially when they involve superstar players. But when they don't work out as intended, it gives us plenty to discuss for years to come.
We're going to look back at some of the more recent blockbuster NHL trades and ponder what could have been, while analyzing what went wrong. Sure, we could go way back, but we're going to try to rein ourselves in a little.
San Jose Sharks Trade Erik Karlsson to Pittsburgh Penguins
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We're not sure anyone is celebrating the anniversary of the Erik Karlsson trade from the San Jose Sharks to the Pittsburgh Penguins.
The Pens added the 35-year-old coming off his massive 101-point season in which he won the Norris Trophy despite the Sharks being one of the worst teams in the league with 60 points.
It was an incredible season for Karlsson, given everything going on with San Jose and its top players being injured or having aged out of town already.
The Sharks knew they had to rebuild, and the Penguins had to do something to keep the dream of winning one more Stanley Cup alive for Crosby, Malkin and Letang. Adding Karlsson to the lineup sounded like a great idea, but in practice, it threw a lot of the team's chemistry out of synch, and Pittsburgh couldn't afford to be "off" at all if they were going to get back to the playoffs.
Mikael Granlund had a solid enough time with the Sharks to land them a first-round pick when they traded him last season to Dallas, while Jan Rutta and Mike Hoffman didn't have as good a time.
The first-round pick they got from Pittsburgh was used in a trade with Buffalo to move up and take defenseman Sam Dickinson, who figures to be a cornerstone on the blue line of their rebuild.
Winnipeg Jets Send Evander Kane to Buffalo Sabres
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As far as blockbusters go, former Buffalo Sabres general manager Tim Murray went all-in to make a massive splash in 2015.
As part of a monster deal with the Winnipeg Jets that involved eight players and picks, he acquired Evander Kane, Zach Bogosian and a prospect in exchange for Drew Stafford, Tyler Myers, Joel Armia, Brendan Lemieux and a 2015 first-round pick.
At the time the Sabres added Kane and Bogosian, Kane was out for the season with an injury. He had also, reportedly, become an outcast in the Jets locker room and GM Kevin Cheveldayoff had to make a move to calm things down.
Murray was eager to make a trade that would help set the Sabres up for the following season when he hoped to have Connor McDavid or Jack Eichel as the face of the franchise, and the team's efforts to get as low in the standings to help make that happen were only helped out by making this massive trade.
Kane lasted nearly three seasons in Buffalo before he was traded to San Jose and peaked in 2016-2017 with 28 goals. There were legal issues, there was a missed practice in 2016 because he overslept after he was out late partying in Toronto during NBA All-Star Game weekend and, no, the Sabres never made the playoffs while he was there.
Given everything that went on with him in Buffalo, you could argue having Eichel and Sam Reinhart to grow up with him may not have been ideal, but that's more for Sabres fans to chew on as they wait for their team to get back to the postseason.
Philadelphia Flyers Deal Eric Lindros to New York Rangers
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Let's turn the clock back to 2001 for this Eric Lindros trade.
The Philadelphia Flyers sent Lindros and a conditional 2003 pick to the rival Rangers for Jan Hlavac, Kim Johnsson, Pavel Brendl and a 2003 third-round pick.
The trade came after Lindros sat out the entire 2000-2001 season as he and then-Flyers GM Bobby Clarke feuded over Lindros' fitness and Clarke stripping him of the captaincy. Lindros wanted to play for the Toronto Maple Leafs, but Clarke refused to trade him where he wanted.
Instead, the Rangers stepped up and offered breakout goal scorer Hlavac, a steady defenseman in Johnsson and the No. 4 pick in the 1999 draft in Brendl to get Lindros.
Hlavac never found his goal scoring again after leaving New York and Johnsson proved to be a very good defender. Brendl, meanwhile, became one of the all-time biggest draft busts in history.
Lindros succeeded with the Rangers in his first season and put up 37 goals and led the team in scoring with 73 points. Things dropped off after that in a big way, though. He went from 73 points to 53 to 32 points in 39 games in 2003-2004 as injuries derailed his season.
Neither team came out ahead on the deal, and the damage done between Lindros and Clarke wasn't patched up until the Rangers and Flyers met in the NHL Winter Classic in 2012 in Philadelphia. That's a happy ending, at least.
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Boston Bruins Trade Phil Kessel to Toronto Maple Leafs
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For years, there was no trade that was arguably more infamous than the Phil Kessel move out of Boston to Toronto.
Toronto Maple Leafs GM Brian Burke never feared making a bold move, and he made a massive splash by acquiring Kessel from the Bruins before the start of the 2009-2010 season in return for the Leafs' first- and second-round picks in 2010 and their first in 2011.
At the time, Kessel was an RFA with Boston and talks were going poorly, to say the least. Even though the Leafs weren't a playoff team at the time and giving up multiple top picks was a huge gamble, Burke gave it all up to add Kessel, who just had 36 goals and 60 points the previous year at age 21.
Kessel was a very good player for the Leafs. He scored 30-or-more goals four times in six seasons in Toronto, but the team made the postseason once in those six years (in 2013) and lost to the Boston Bruins in an incredible seven-game series. In that series, the Leafs had to try to wrangle both Tyler Seguin and Dougie Hamilton.
Seguin was taken by the Bruins with the pick they got from Toronto in 2010 and Hamilton with the Leafs' 2011 pick. Seguin was a young part of the Bruins' 2011 team that won the Cup as well.
Despite how good Kessel was, he wasn't enough to lift the entire team (not his fault) and even though banners fly forever and the Bruins can claim they won that trade, Seguin and Hamilton weren't long for Boston themselves.
Boston Bruins Trade Tyler Seguin to Dallas Stars
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Following the Bruins' loss to the Chicago Blackhawks in the 2013 Stanley Cup Final, Tyler Seguin's welcome in Boston had worn out. Management seemingly wasn't a huge fan of his style of play and felt he wasn't mature enough for what was a veteran team.
Seguin's production in his last year in Boston (32 points in the 48-game lockout-shortened season) and his seven points in the playoffs weren't enough to get management to go to bat for him and it shipped him to the Dallas Stars, who were eager to add a young potential superstar.
The Bruins and Stars pulled off a major deal that saw Seguin and Rich Peverley go to the Stars for Loui Eriksson, Joe Morrow, Matt Fraser and Reilly Smith.
Whether Seguin took the trade as a wake-up call or his game naturally matured, it worked for the Stars. He scored 37 goals in his first two seasons with Dallas and 33 in the one after that, with a 40-goal season two years later.
He's been a huge player for the Stars, and it was a trade they clearly got right and even included a Stanley Cup Final appearance in the 2020 bubble.
Giving up Seguin didn't directly hinder what the Bruins were doing. Their team was centered around Zdeno Chara, Patrice Bergeron, Brad Marchand and David Pastrnak, and they got back to the Cup Final in 2019.
You can't help but wonder if maybe Seguin would have helped them beat the St. Louis Blues that year.
New York Islanders Acquire Alexei Yashin from Ottawa Senators
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Turned out that 2001 was a big year for trades involving both New York area teams.
While the Rangers landed Eric Lindros, the New York Islanders got bold for a big-time center themselves when they added Alexei Yashin.
Yashin was a big scorer for the Ottawa Senators. In his final four seasons there, he had 329 points in 328 games, including 152 goals. He had back-to-back 40-goal seasons, sort of, as a contract dispute after he scored 44 in 1998-1999 kept him out of the 1999-2000 season.
That dispute led to Ottawa trading him after he put up 40 in 2000-2001 and it was the Islanders and GM Mike Milbury who swooped in with an offer the Sens couldn't refuse.
The Isles sent winger Bill Muckalt, 24-year-old defenseman Chara and their first-round pick in the 2001 draft, No. 2 overall, to Ottawa for Yashin. The Senators took Jason Spezza with the pick. Yashin, meanwhile, signed a 10-year, $87.5 million contract with the Islanders.
With the Islanders, Yashin was not nearly as effective a player as he was with Ottawa and the Isles bought him out of his contract in 2007.
We know Isles fans don't have a lot of reasons to think about the Milbury days as GM, but this trade was a brutal one, given that Chara exploded immediately in Ottawa and Spezza was one of their best forwards while they climbed to the top of the East in the years that followed.
That Ottawa allowed Chara to get away years later to Boston isn't much of a salve, though.
San Jose Sharks Add Erik Karlsson from Ottawa Senators
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Wait a minute, didn't we just see you?
When the Sharks acquired Erik Karlsson from the Ottawa Senators in 2018, they assuredly thought they found the player who would help them get back to the Stanley Cup Final.
After all, the Sharks were just there in 2016 and Karlsson nearly helped the Senators get to the Final instead of Pittsburgh in 2017.
San Jose was so sure of this, it gave up prospect forward Josh Norris, Rudolfs Balcers, Chris Tierney, Dylan DeMelo and a pile of picks, including two first-round selections. The 2020 first it allowed Ottawa to select Tim Stützle.
In five seasons with the Sharks, Karlsson made it to the postseason once and that happened in his first year with them in 2018-2019 when they advanced to the Western Conference Final. He had 16 points in 19 games before they bowed out to the St. Louis Blues, but that proved to be the only time they made it to the playoffs.
Karlsson won the Norris with San Jose, but the team was terrible, and he was traded immediately after that season to Pittsburgh. It was a gutsy move by then-GM Doug Wilson to add him, but it didn't work out.
If there's any consolation for the Sharks, it's that Ottawa didn't exactly clean up with the trade, either. Stützle has been an outstanding player and Norris showed a lot of promise before shoulder injuries kept him off the ice before he was traded to Buffalo for Dylan Cozens last season.
Edmonton Oilers Trade Taylor Hall to New Jersey Devils for Adam Larsson
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Of the many fine moments in Bob McKenzie's journalism career, the way he dropped the news of the Edmonton Oilers trading 2010 No. 1 pick Taylor Hall to the New Jersey Devils is one of the most memorable.
The buildup on Twitter that summer day in 2016, in which an assortment of wild moves and news occurred (P.K. Subban for Shea Weber; Steven Stamkos saying he was staying with the Tampa Bay Lightning) and then seeing Hall dealt one-for-one for a defenseman who was the fourth overall pick in 2011 was mind-blowing.
The Oilers were disappointed with how Hall had grown in Edmonton and watching his draft classmate, Tyler Seguin, win a Stanley Cup with Boston in 2011 and then explode with the Dallas Stars was too much to bear.
Edmonton needed to be better defensively and opted to part ways with the still-productive Hall to do it.
Fittingly enough, Hall exploded with the Devils and went on to win the MVP award two years later when he had 39 goals and 93 points. Injuries wrecked him the two years that followed his Hart Trophy win, however.
Larsson's time in Edmonton went about as well as the start of his career with the Devils. He was a steady defensive defenseman but wasn't a Norris-caliber player. In five seasons, he had 68 points with 16 goals but was left exposed for the expansion draft in 2021 and was selected by the Seattle Kraken.
The trade was one-for-one, but the end result was none-for-none.
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