Connecting the Wayne Gretzky and Erik Karlsson Trades

Finally, the hard-hitting trade analysis you’ve been waiting for.

It’s been nearly 32 years since the Edmonton Oilers shockingly traded Wayne Gretzky to the Los Angeles Kings on August 9th, 1988. While every year we hear everyone reminisce over where they were when they first heard the news, lost is the fact that the trade ended up spiraling into a massive chain that can be connected to almost any future trade imaginable.

Players such as Phil Kessel, Jamie Benn, Brad Marchand and many others are on their respective teams because of the butterfly effect that this trade (and many others before it) put into motion.

The Ottawa Senators have also had their fair share of blockbuster trades lately, with none bigger than went they sent their captain and mega-superstar Erik Karlsson to the San Jose Sharks, receiving six pieces in return that are not Erik Karlsson.

Long-time readers may remember a similar exercise I did back in 2017 that connected the Phil Esposito trade of 1967 to the Dion Phaneuf trade of 2016. Using the same method, we can connect Gretzky to Karlsson through 18 steps, including some of the biggest, best and worst trades of the last thirty years.

“Even Wayne Gretzky was traded.” —Pierre Dorion

The ground rules are: if someone involved in a trade was later dealt to another team, that counts a connection. If a draft pick was involved in a trade, the player being taken with that pick counts as a connection. If a player retires, signs somewhere else through free agency, or is claimed off waivers, the chain breaks. Sounds simple enough, so let’s begin!

(Players involved in completing the connection will be marked in italics.)

Step 1: Edmonton trades Wayne Gretzky, Mike Krushelnyski and Marty McSorley to Los Angeles for Jimmy Carson, Martin Gelinas, 1989 1st round pick, 1991 1st round pick, 1993 1st round pick and cash
August 9th, 1988

It’s here where our journey begins. This was the blockbuster to top all blockbusters, and the one that gets dissected to death every August. The Great One was headed to the West coast, shaking up the hockey world like no one had ever see before.

Instead of breaking down how the players fared, I’ll leave you with the much more interesting fact that the Mark Messier trade actually still has direct roots to current Oilers forward Andreas Athanasiou, with no moving from team to team like we’ll be doing. The Gretzky trade unfortunately doesn’t have a direct line anymore, but it’s neat to see how old trades can still have current effects.

However, in the name of searching for a connection to Karlsson, the player we have to follow first is Marty McSorley, one of the two players who went to the Kings along with Gretzky. He’d go on to become the Kings’ all-time leader in penalty minutes with 1846.

Step 2: Los Angeles trades Marty McSorley to Pittsburgh for Shawn McEachern
August 27th, 1993

After five seasons with the Kings, McSorley was moved to the Pittsburgh Penguins in a one-for-one trade for Shawn McEachern, who you may recognize as one of the Senators’ key forwards in late 90’s/early 2000’s. This wouldn’t be the only trade that involves both of these players...

Step 3: Pittsburgh trades Marty McSorley and Jim Paek to Los Angeles for Shawn McEachern and Tomas Sandström
February 15th, 1994

After less than a year with each player, the Penguins and Kings must’ve been dissatisfied with the earlier swap, sending both McSorley and McEachern back to their previous teams. But with McEachern’s point totals falling on the Kings, the Penguins were able to capitalize by bringing in Tomas Sandström, who was scoring much more than depth player Jim Paek who went the other way.

Like McEacherm, Paek would later go on to play for the Sens, albeit for only a very limited 29 games.

Step 4: Pittsburgh trades Shawn McEachern and Kevin Stevens to Boston for Glen Murray, Bryan Smolinski and 1996 3rd round pick
August 1st, 1995

We continue to follow the trade path of McEachern, who just couldn’t find himself a long-term home. We also encounter another future Senator in Bryan Smolinski, who at the time was a young centreman just entering his prime years.

Neither player was dealt as the centrepiece of the trade, however, as Kevin Stevens was just a couple years removed from back-to-back seasons with over 110 points. He’d end up returning to the Penguins late in his career, where he’d eventually retire.

Step 5: Pittsburgh trades Bryan Smolinski to the New York Islanders for Andreas Johansson and Darius Kasparaitis
November 17th, 1996

To connect to Karlsson, we have to keep following Smolinski, who like McEachern took a while to settle into a team. Smolinski was the key piece this time after having a breakout 64-point season with the Penguins, but despite helping the Pittsburgh make a run to the Eastern Conference Finals, they sent him packing for two depth players.

Darius Kasparaitis, one of the few Lithuanians in NHL history, was failing to meet expectations on the Islanders after being selected 5th overall in 1992. Andreas Johansson was also a fringe NHLer who had only recently come over from Sweden. And like many players already mentioned, he too would later go on to play for the Sens!

Step 6: The New York Islanders trade Bryan Smolinski, Marcel Cousineau, Zigmund Pálffy and 1999 4th round pick to Los Angeles for Mathieu Biron, Josh Green, Olli Jokinen and 1999 1st round pick
June 19th, 1999

We’ve gone through quite the journey with Smolinski, and this is the last we’ll be seeing of him in this chain (although his next deal is when he finally ends up in Ottawa). The New York Islanders missed the playoffs for their fifth season in a row and needed to shake things up, sending Zigmund Pálffy, who had 50 points in 50 games, to the Kings.

The return was sizeable, acquiring recent 1st round pick and 6’6” defenceman Mathieu Biron, the 8th overall pick who they’d use to select Taylor Pyatt a week later, and some young guy by the name of Olli Jokinen, the 3rd overall pick from 1997 who was just getting his feet wet in the NHL. Seems like a great young piece to hold onto, right?

Step 7: The New York Islanders trade Olli Jokinen and Roberto Luongo to Florida for Oleg Kvasha and Mark Parrish
June 24th, 2000

Apologies to any Islanders fans reading this who are now being reminded of the Mike Milbury era. You have my sympathy.

In what’s since been labeled as one of the worst trades in NHL history, Jokinen was flipped just over a year after the Islanders acquired him, as his 21 points in 82 games still wasn’t living up to the Islanders hopes. But along with Roberto Luongo, New York’s 4th overall pick from 1997, they were shipped off to the sunshine state despite missing the playoffs for the sixth straight season.

Those two players, of course, would wind up being two of the greatest players in Florida Panthers history, with Jokinen leading the franchise in all-time scoring until he was recently surpassed by Jonathan Huberdeau. Luongo would also make his first All-Star appearance as a Panther in 2003-04 before heading to Vancouver.

As for the Islanders, Oleg Kvasha and Mark Parrish were fine players, but they were no Jokinen or Luongo, as they would go on to miss the playoffs for a seventh straight season. Fortunately for us, it’s Parrish who helps keep the connection going.

Step 8: The New York Islanders trade Mark Parrish and Brent Sopel to Los Angeles for Denis Grebeshkov, Jeff Tambellini and 2006 conditional pick
March 8th, 2006

Parrish would stick with the Islanders for a while, even scoring a 60-point season in 2001-02. As another fun fact, his final season of professional hockey ended up being with the Binghamton Senators! We’re just pulling out all the Sens connections today.

We have to loop back to the LA Kings to keep this chain going, as Parrish’s Long Island tenure came to an end in 2006. The Islanders were trying to get younger (again), bringing in Denis Grebeshkov and Jeff Tambellini (brother of former B-Sens player Adam Tambellini), who were first round picks in 2002 and 2003 respectively. Hint: neither player really worked out for the Islanders.

Step 9: Los Angeles trades Brent Sopel to Vancouver for 2007 2nd round pick and 2008 4th round pick
February 26th, 2007

Following Brent Sopel, there’s not a whole lot to dissect about this next trade. It was the day before the trade deadline, and Luongo’s Canucks were gearing up for a deep playoff run. Let’s see who that second round pick ended up being...

Step 10: Los Angeles uses 2007 2nd round pick to select Wayne Simmonds
June 23rd, 2007

It’s Wayne Simmonds! The defining power forward of the 2010s finds himself in the midst of this trade chain, now having gone from one Wayne to another.

Step 11: Los Angeles trades Wayne Simmonds, Brayden Schenn and 2012 2nd round pick to Philadelphia for Rob Bordson and Mike Richards
June 23rd, 2011

Although Simmonds had some good seasons with Los Angeles, it would be in Philadelphia where his most memorable moments would come. This trade looks extremely lopsided today, as Flyers captain Mike Richards was nearing the tail of his career, while Brayden Schenn, the 2009 5th overall pick, has blossomed into a fantastic top-six centre. But the Kings also went on to win two Stanley Cups with Richards, so I’ll leave the judgement up to you.

There were many great pieces were involved in this trade, but it’s actually the 2012 second round pick that we have to follow to keep us on track. We’re getting closer!

Step 12: Philadelphia trades 2012 2nd round pick and 2013 3rd round pick to Dallas for Nicklas Grossmann
February 16th, 2012

And we’re back to the classic deadline moves. Depth defender Nicklas Grossmann was being dangled by the Dallas Stars prior to the 2012 trade deadline, and the Flyers pounced sending two picks the other way. We’ll continue to follow the 3rd round pick, but the 2012 2nd rounder ended up being used to select Devin Shore, who a few trades later now plays for the Columbus Blue Jackets.

Step 13: Dallas trades 2013 3rd round pick and Brenden Morrow to Pittsburgh for 2013 5th round pick and Joe Morrow
March 24th, 2013

With an extra 3rd round pick in hand from trading Grossmann, the Stars packaged it with the aging Brenden Morrow for another un-related Morrow, defenceman Joe Morrow.

There’s two fun facts here. First, the 3rd round pick that we’ve been following since Grossmann was used by the Penguins to select none other than Jake Guentzel. Second, with Morrow serving as the Stars’ captain at the time of the trade, that now makes him the third captain to be traded so far in this chain, along with Gretzky and Richards. And I’m sure you can guess who will be fourth.

Step 14: Dallas trades Joe Morrow, Loui Eriksson, Reilly Smith and Matt Fraser to Boston for Tyler Seguin, Rich Peverley and Ryan Button
July 4th, 2013

...oh god...

Just as it seemed like things were calming down in this chain, we hit another blockbuster, with this one even more infamous than the Luongo and Jokinen trade. Joe Morrow, the connector, is nothing but a throw-in for this transaction, as the Boston Bruins foolishly gave up on a young Tyler Seguin in exchange for some older, far less effective players.

A couple paragraphs will never be able do this trade justice, and I can only hope we one day get a documentary to see how it all unfolded.

Oh wait, we already did :)

Step 15: Boston trades Reilly Smith and Marc Savard to Florida for Jimmy Hayes
July 1st, 2015

Of all the mediocre pieces the Bruins got in return for Seguin, the player working out best for them was Reilly Smith. Now in his young prime years, his 91 points over two seasons provided some excellent high-end depth to their competitive forward corps.

But with Marc Savard bogging down their cap space, they had to find a way to get him off the books, and Smith was the player required to make it happen.

We’re going to have to continue following Smith, whose time with the Panthers was even more fruitful than with the Stars or Bruins, driving play in the Panthers’ top-six. Fast forward to 2017...

Step 16: Florida trades Reilly Smith to Vegas for 2018 4th round pick
June 21st, 2017

Good lord, it’s another awful trade.

This one requires some context. With the Vegas Golden Knights entering the NHL as the league’s 31st franchise, they held plenty of leverage on teams who were looking to protect their players in the expansion draft. The Panthers’ front office saw themselves as being in a hole, as they wanted to preserve their defensive corps that included Alex Petrovic and Mark Pysyk.

That still left some players unprotected that they didn’t want to be taken, and Reilly Smith apparently wasn’t one of them. For only a 4th round pick in return, he was sent packing to Vegas on the agreement that the Golden Knights would pick the specific player that Florida chooses. Of course, that player was another key forward in Jonathan Marchessault, as he and Smith ended up leading the Golden Knights to a historic Stanley Cup Final run in their inaugural season.

Unlike Mike Milbury, Dale Tallon is still in the Florida front office. My condolences to their fans.

Step 17: Florida trades 2018 4th round pick, 2018 5th round pick and 2019 2nd round pick to San Jose for Mike Hoffman and 2018 7th round pick
June 19th, 2018

We’re so close!

This deal doesn’t require much an introduction on this website, as the entire Mike Hoffman saga still feels like a fresh wound. In what was an ugly feud of online harassment, with Hoffman’s significant other directing hateful online comments at Karlsson’s wife Melinda, Hoffman was sent as far away from Ottawa as possible to San Jose, for veteran Mikkel Boedker and down-trending prospect Julius Bergman.

What Pierre Dorion hadn’t considered was exactly what happened next, as the Sharks made a deal with the Panthers to flip Hoffman for a much better return of future assets, something the middling Senators had confusingly passed up. The Sens were in a corner, but in what’s been an embarrassing handful of years for the organization, this one still sticks out.

Step 18: San Jose trades 2019 2nd round pick, Josh Norris, Chris Tierney, Rudolfs Balcers, Dylan DeMelo, 2019/2020 1st round pick and two more conditional picks to Ottawa for Erik Karlsson and Francis Perron
September 13th, 2018

That leads us directly to our goal, the Erik Karlsson trade of September 13th, 2018. The 2nd round pick the Sharks acquired for Hoffman was flipped to Ottawa to secure the star defender, which Ottawa would later end up flipping to Carolina to move up to draft Mads Søgaard.

I won’t go on about whether this trade has been a win or loss for the Senators, you can make your own judgement on that. But I think I can speak for most Senators fans that we can remember exactly how that September 13th played out, just like everyone can with the Gretzky trade over 30 years prior.