15 HUGE NHL Deals That Nearly Happened Since 2000

As sports fans, there’s nothing we like more than a big blockbuster trade, and why shouldn’t we? Sometimes these trades can alter the landscape of the game as we know it. To corroborate this point, look no further than the trade sale of Wayne Gretzky back in 1988. Without that trade sale, it’s fair to ponder whether hockey would have ever taken off in California to the degree that it has.

It can be fun to think about how things could have been different if things hadn’t have happened the way they did—not just with the trades that did happen, but also with trades (or even signings) that ALMOST happened.

It can sometimes be difficult to gauge the validity of trade rumors when you hear them, so it’s important to take each with a grain of salt. Some of these rumored deals tend to be more verifiable than others, as often times a GM will reveal years later a deal that fell through at the 11th hour during a past tenure with a certain club.

Yes, we hockey fans love a good trade rumor. Today’s list takes a look at some of the biggest (and somewhat verifiable) trade and/or signing rumors since the turn of the millennium that never came to fruition, for whatever reason. In some of these cases, the reason is well documented, while in others they're a little more mysterious. Either way, the NHL sure would have a different look today if all of these deals went through. Enjoy:


15 Tyler Seguin for Thomas Vanek

Jerome Miron-USA TODAY Sports

The Tyler Seguin trade made by then-Bruins GM Peter Chiarelli remains one of the more lopsided deals in recent history, but apparently there was another offer on the table that was ultimately kibosh'd by the Sabres. The Bruins wanted Thomas Vanek and some additional, non-specific accoutrements in exchange for the rising Seguin, but Buffalo refused to bite.

I’m sure if the Sabres could do it again they’d pull the trigger on the deal, though I’m unclear on what the additional pieces were. Still, though, Buffalo has been in rebuilding mode ever since this deal fell through, and Vanek hasn’t been a member of the club for nearly just as long, and he's regressed mightily to boot. Seguin, meanwhile, is still a superstar center in the league. What might have been…

14 Michael Nylander Signs in Edmonton… PSYCH!

Via: Hockeysverige

It was the summer of 2007, and despite a rough season, the Oilers and their brass still felt like they were just a few key pieces away from the promise land. They were incorrect on this of course, as the Oilers wouldn’t return to the postseason for another decade, but they nonetheless aggressively pursued free agents that year, and they had reportedly reached an agreement with Swedish UFA Michael Nylander.

The news hit the headlines before pen went to paper, which is never good for PR. Rumor has it that Nylander’s wife looked at a map and discovered where Edmonton was after hearing of her husband’s plans to sign there, and it didn’t take her long to nix the plan. Nylander ended up signing in Washington, angering Oilers GM Kevin Lowe and all of the club’s fans.

13 Shea Weber Signs Offer Sheet With Philly

Eric Hartline-USA TODAY Sports

The reason Shea Weber is on a ridiculous contract that takes him into his 40s with an annual cap hit of $7.857 million is because back in 2012, with Weber an RFA, the Flyers signed the d-man to a 14-year deal worth $110 million. The Predators, who still held Weber's rights, had already lost Ryan Suter in free agency that summer, did not want to lose both of their top rearguards in one summer. Two losses like that could have seriously demoralized the franchise and its fans who were just starting to become the passionate bunch they are now.

Despite the contract being less than ideal, the Preds matched the offer, preventing a move to Philly for Weber. Had the Preds not matched, Weber would probably still be in Philly today, and the whole P.K. for Weber deal may have never happened.

12 The Flames/Ryan O’Reilly Offer Sheet Debacle

Timothy T. Ludwig-USA TODAY Sports

This one only sort of qualifies for the list, but I wanted to include it simply because the situation was so bizarre. Calgary GM Jay Feaster signed restricted free agent Ryan O’Reilly to an offer sheet that was immediately matched by the Colorado Avalanche. Had they declined to match, the move would have cost Calgary a 1st and 3rd round pick.

As it turns out, however, the Flames are darn lucky that Colorado chose to match the offer. Had they not, O’Reilly would have had to clear waivers before joining the Flames (this is because he had played a few games overseas that season). No chance O'Reilly would have cleared waivers. Imagine that: the Calgary Flames would have surrendered a 1st and 3rd round pick and had nothing to show for it.

11 Jeff Carter to T.O. for Tomas Kaberle

Perry Nelson-USA TODAY Sports

During his 12 season tenure with the Toronto Maple Leafs, Tomas Kaberle’s name was pretty much always in the rumor mill. The one that seems to have the most validity was in 2008, when Toronto GM Cliff Fletcher had a deal in place that would see him acquire Jeff Carter and a 1st overall pick from the Philadelphia Flyers for Kaberle.

It was actually the Toronto defenceman himself who vetoed the deal, apparently refusing to waive his no-trade clause to go to the City of Brotherly love. This potential trade would have happened in the middle of Carter’s breakout season, and the very next year he took another giant step forward, potting 46 goals and 84 points, which the Leafs could have certainly used at that time.

10 Cory Schneider for Gilbert Brule

Marilyn Indahl-USA TODAY Sports

Okay, this trade may not have altered the course of either franchise in any meaningful way, but if this trade did go down when it was in the rumor mill in 2008, it would have been terribly lopsided. What’s interesting is that according to then-Columbus GM Doug MacLean, he was offered Cory Schneider for Gilbert Brule, straight across.

Both Brule and Schneider were considered top prospects at the time, but MacLean chose to reject Dave Nonis’s offer. In hindsight this looks like a terrible error on both parts, but at the time the decision could have seemed calculated. Forwards are usually easier to gauge as prospects, whereas top goalie prospects frequently tend to fizzle out as they age. Nonetheless, Brule fizzled out in this case, and Schneider became a top 15 goalie in the league.

9 Jordan Eberle for Ryan Johansen


Does anybody remember that ridiculous documentary series called “Oil Change” from a few years back? I think the team had to stop producing them because they kept finishing bottom three in the league, and nothing changed year over year aside from the coaching staff and depth players. Nonetheless, it was in the first edition of “Oil Change” where we learned of the potential trade then-GM Steve Tambellini had lined up: Jordan Eberle for the pick that would have been Ryan Johansen.

Well, to say he had it lined up is a stretch. He was calling Doug MacLean, inquiring what it would take to pry the 4th overall pick away from the Jackets. MacLean wanted Eberle, who hadn’t yet made his NHL debut but had already made waves by starring in three consecutive World Juniors. This would have been an interesting trade, because Eberle burst onto the NHL scene and scored 76 points in his sophomore year, but Johansen is definitely the better player today.


8 Claude Giroux for Paul Ranger

Eric Hartline-USA TODAY Sports

This would have been unbelievable had it went down; alas, it did not. But it was apparently rejected by the Lightning, who viewed Paul Ranger as a major piece of its defense, and to be fair Claude Giroux was already a few seasons into his career at this point and had yet to establish himself as the lethal offensive weapon he was to soon become.

Hindsight is always 20/20, but Ranger requested to leave from the Lightning early in the 2009-10 season, citing “personal reasons” as the motive. Shortly thereafter, Giroux started producing points at an elite rate, and despite a down year in 2016-17, he's still considered one of the more dangerous forwards in the NHL. Ranger made a comeback attempt in 2013 with the Maple Leafs, but it failed and he’s now retired from professional hockey.

7 Dany Heatley to Edmonton for a Package


Again, no one knows why this trade was reported before it was made official, but nonetheless it got fans in Edmonton quite excited at the time. When news broke soon after that Dany Heatley had refused to waive his no-trade clause to go to Edmonton, Heatley became public enemy #1 in Northern Alberta. The package reported was a three-for-one deal, with the three being Andrew Cogliano, Dustin Penner, and Ladislav Smid.

Oilers fans were sour on this—as were Sens fans, actually—because Heatley was the one who requested a trade out of Ottawa in the first place. He was instead traded to San Jose for Jonathan Cheechoo, Milan Michalek, and a 2nd round pick that turned into Kent Simpson. In the long run, those two packages were actually pretty comparable (read: both fairly underwhelming).

6 Stamkos to NYR for a Package

Kim Klement-USA TODAY Sports

Steven Stamkos is still one of the most lethal snipers in the league, and despite recent injury troubles, he’s still a top point producer when healthy. During his rookie year in 2008-09, however, he was struggling a bit and the Lightning were apparently actively shopping the sniper. Nothing ever happened of course and Stamkos broke out with 95 points in his sophomore year, making him all but untouchable.

There is no exact package that was ever confirmed, but according to the New York Post the trade with the Rangers was for a package that included two (or three) of Michael Del Zotto, Evgeny Grachev, Ryan Callahan, Brandon Dubinsky, and Dan Girardi. While there are definitely some strong players on that list, I imagine that Lightning fans are still happy that the club practiced patience with Stamkos in hindsight.

5 An Entire Year’s Worth of Draft Picks for Ryan Murray

Aaron Doster-USA TODAY Sports

This one was nothing more than a rumor, as Islanders GM Garth Snow has never commented on this, and the Oilers brass hasn’t publicly confirmed it, either. Nonetheless, when the Oilers held the #1 overall pick at the 2012 NHL Entry Draft, it was reported that Snow apparently offered all of the club’s draft picks that year in order to jump up to #1 in the draft (they sat at #4).

This offer was evidently rejected by Oilers GM Steve Tambellini, who probably feels like a damn fool now, considering how they didn’t even take the player the Islanders were interested in (Ryan Murray), and the player they did take (Nail Yakupov) is now considered one of the bigger busts of the modern day NHL. They have almost nothing to show for that asset today.

4 Pavel Datsyuk for Scott Gomez


As hard as I try, I cannot seem to picture Pavel Datsyuk wearing an NHL jersey that is not a Red Wings sweater. Nonetheless, we apparently came very close to seeing Datsyuk don a New Jersey Devils sweater in 2007. As the trade deadline approached and with Datsyuk on an expiring contract, the Wings were having trouble coming to terms on a new deal.

Apparently the Wings and Devils had a trade lined up that would have sent Datsyuk to New Jersey in exchange for Scott Gomez. At the time this looked like it could have been a fair deal, but the Wings narrowly escaped disaster here, as Datsyuk took his game to the next level in 2007-08, and Gomez signed a fat offseason contract with the Rangers and his game took a sharp nosedive.

3 Corey Perry and a 1st for Mike Comrie

Gary A. Vasquez-USA TODAY Sports

This one seems absolutely astonishing, and it becomes even wackier when you consider that the only reason it didn’t happen is because then-Oilers GM put the kibosh on the whole thing over a $2.5M signing bonus that Mike Comrie had just received and refused to pay back. Before getting into more details here, how ridiculous is it to ask someone for their $2.5M signing bonus back? Did he think he’d just happily hand it over? Words escape me.

Anyway, Corey Perry would have been an Edmonton Oiler, and Comrie would have been a Duck. This all went down back in December 2003, and it’s pretty crazy to think that this was a deal was even on the table. At the time Perry was nothing more than a deep first round prospect, and Comrie still hadn’t received a contract for the 2003-04 season and was holding out. He was eventually dealt to Philadelphia for Jeff Woywitka and two picks (which turned into Rob Schremp and Danny Syvret).

2 Roberto Luongo for Joe Thornton


Two of my favorite NHL players factor into a potential trade that former Panther GM Mike Keenan says almost went down sometime in the mid-2000s. When Luongo and the Panthers couldn’t agree on a contract extension, Keenan was directed by ownership to find a trade for Luongo, and he almost did when he offered the netminder to the Bruins for Joe Thornton.

This was the trade the Bruins offered, which isn’t hugely surprising as he was dealt to San Jose instead for a package that doesn’t quite measure up to Roberto Luongo. Unfortunately for the Panthers, Thornton’s contract also scared ownership away, and Luongo was eventually dealt to Vancouver in the 2006 offseason for Todd Bertuzzi, Bryan Allen, and Alex Auld.

1 Carey Price + for Vincent Lecavalier

Eric Bolte-USA TODAY Sports

There is little confirmed information out there regarding this potential deal, but let’s just say if it happened the Montreal Canadiens would look mighty different today. There’s no consensus on what exactly that “+” is in this case, but there are reports that Montreal had offered up goalie Carey Price, Max Pacioretty, and P.K. Subban for Vincent Lecavalier in 2009. So, yeah, basically the core of their future for a depreciating asset.

Vinny was still on top of his game, mind you, and widely recognized as one of the best players in the NHL. Still, though, if that rumored package was accurate, that’s quite a ransom to pay for a player who was already 30 and about to regress. Former Habs GM Bob Gainey refutes this, and says the additional players in the deal were Tomas Plekanec, Chris Higgins, and Josh Gorges, which would be a much easier pill to swallow long-term.


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