The thing about Dylan Larkin asking for a trade from Detroit is that it shouldn’t be surprising, and yet it is.
He’s 29. He’s from Michigan. He’s the captain. He signed the extension. He did everything you’re supposed to do if you’re a franchise player who believes in the project. And after years of “the rebuild is almost there,” he’s apparently decided it isn’t — or at least that he doesn’t want to keep finding out.
Sportsnet’s Elliotte Friedman broke the news on June 5th. ESPN confirmed it. The Red Wings now have a very uncomfortable summer ahead of them. To quote Jason Spezza: “Summer can be a distraction when someone asks for a trade request”.
Larkin isn’t the first star to force a franchise into this kind of moment. Some of those situations were uglier. Some were sadder. A few of them ended with the player hoisting the Cup somewhere else, which is the nightmare scenario for Detroit fans right now.
Famous NHL Trade Requests Through the Years
From Eric Lindros refusing Quebec to Dylan Larkin reportedly asking out of Detroit, star trade requests have shaped some of the NHL’s biggest franchise turning points.
- 1991Eric Lindros Refuses to Play for Quebec
Lindros was selected No. 1 overall by the Nordiques but refused to join the franchise, eventually forcing one of the biggest trades in NHL history.
- 1995Patrick Roy’s Montreal Exit Changes Everything
Roy’s relationship with the Canadiens collapsed after the infamous Detroit blowout, leading to a trade to Colorado and another Stanley Cup.
- 2006Chris Pronger Asks Out of Edmonton
Pronger requested a move shortly after helping the Oilers reach Game 7 of the Stanley Cup Final, making the timing especially painful in Edmonton.
- 2009Dany Heatley’s Senators Saga Gets Messy
Heatley wanted out of Ottawa, then reportedly blocked a potential move to Edmonton before eventually landing with the Sharks.
- 2014Jason Spezza Leaves Ottawa
Spezza’s request carried extra weight because he was the Senators’ captain, making his departure another reminder that the “C” does not always guarantee a long-term fit.
- 2016Jonathan Drouin’s Tampa Bay Standoff
Drouin’s situation became public and awkward when he refused to report to the AHL, though he later returned before eventually being traded to Montreal.
- 2021Jack Eichel and Buffalo Reach a Breaking Point
Eichel’s trade request became a full organizational standoff over losing, injury treatment, surgery preference and the direction of the Sabres.
- 2021Pierre-Luc Dubois Exits Columbus
Dubois’ desire to leave became impossible to ignore, with his final games under John Tortorella turning visibly uncomfortable before the Winnipeg trade.
- 2022Matthew Tkachuk Forces Calgary’s Hand
Tkachuk told the Flames he would not sign long term, leading to a blockbuster move to Florida and a major shift in both franchises’ futures.
- 2026Dylan Larkin Reportedly Asks Out of Detroit
Larkin’s reported request is especially significant because he is the Red Wings’ captain, a Michigan native and the face of the Yzerman-era rebuild.
Patrick Roy, Montreal, 1995
Start here. Always start here.
Roy got lit up by Detroit – nine goals, the kind of game that ends careers – and the Canadiens left him in the net for most of it. When coach Mario Tremblay finally pulled him, Roy walked past the bench and told team president Ronald Corey, loud enough for cameras to catch it, that he’d played his last game in Montreal.
He meant it. Colorado got him within days. He won the Cup that same spring.
What makes this the standard is the specificity of the humiliation. It wasn’t a quiet meeting or a leaked report. It was a blowout, a delayed hook, and a public declaration in real time. The relationship didn’t slowly deteriorate. It detonated.
Eric Lindros, Quebec, 1991
Lindros never actually played for the Nordiques, which makes this entry strange – but it belongs here because it’s the original proof that a player could simply refuse. Quebec drafted him first overall. He said no thanks. He went to Philly instead.
The return package eventually became the spine of the Colorado dynasty (Peter Forsberg, Ron Hextall, Mike Ricci, Steve Duchesne, Kerry Huffman, Chris Simon, two first-round picks – some of which were used to eventually get Patrick Roy). So Quebec lost Lindros and, in a roundabout way, kind of won anyway. Doesn’t make the standoff any less wild in retrospect.
Jack Eichel, Buffalo, 2021
The neck surgery dispute is what turned a bad situation into a genuinely bitter one. Eichel wanted a specific procedure. The Sabres said no. They stripped him of the captaincy. He got traded to Vegas, got the surgery he wanted, and won the Stanley Cup in 2023.
For Larkin comparisons, this is the one Detroit fans will keep coming back to. It’s not a perfect parallel – Larkin’s situation doesn’t seem to involve any personal animosity, at least not publicly – but the shape of it rhymes. Captain. Long rebuild. Decides enough is enough. Leaves. Wins.
Chris Pronger, Edmonton, 2006
The timing is what makes this one hurt to even read about. Pronger helped drag Edmonton to Game 7 of the Stanley Cup Final. They lost, but barely. He was the best defenseman on the ice throughout. Then, weeks later, he asked out.
Anaheim got him. Anaheim won the Cup the next year.
Edmonton spent years rebuilding around what Pronger had shown was possible, then watched him do it elsewhere almost immediately. That’s a specific kind of misery.
Dany Heatley, Ottawa, 2009
This one is less tragic and more just… irritating, even at a distance. Heatley wanted out. Ottawa found a trade – Edmonton. Heatley blocked it with his no-trade clause. Eventually they got him to San Jose.
There’s something uniquely maddening about a player who forces a trade and then vetos the trade. You can’t really get mad at a guy for using the contractual rights he was given, but Ottawa fans did anyway. Reasonably. At least we got a classic clip out of it.
Jason Spezza, Ottawa, 2014
Spezza’s trade request carried extra weight because he was the Ottawa Senators’ captain at the time. After Daniel Alfredsson’s exit the year before, Spezza asking out felt like another painful reset for the franchise. It was not as explosive as Patrick Roy’s Montreal exit or as ugly as Dany Heatley’s Senators saga, but it was still awkward because Ottawa was losing another face-of-the-franchise player.
Spezza eventually landed with the Dallas Stars, giving him a fresh start away from the pressure of the Canadian market while leaving Ottawa to explain why another captain had moved on.
Jonathan Drouin, Tampa Bay, 2016
Most players on this list were established stars when they asked out. Drouin was 21 and still fighting for ice time.
He refused an AHL assignment to Syracuse. Tampa suspended him without pay. The whole thing felt like it was heading somewhere ugly and permanent.
It didn’t. Drouin eventually came back, played real minutes for the Lightning, and wasn’t actually traded to Montreal until 2017 – more than a year later. No dramatic exit. Just two sides grinding through a damaged situation until a deal finally got done.
That quiet awkwardness is underrated as a category. Not every trade request ends with a clean break. Sometimes it just hangs there.
Pierre-Luc Dubois, Columbus, 2021
The benching. That’s the image people remember.
Tortorella pulled Dubois mid-shift for what looked like a disinterested, going-through-the-motions few seconds, and the camera cut to the bench, and it was obvious – visibly, undeniably obvious – that this was over. Columbus traded him to Winnipeg for Patrik Laine not long after.
Most trade requests are invisible until they’re reported. This one you could watch happen.
Matthew Tkachuk, Calgary, 2022
No explosion. No benching. No public declaration. Tkachuk simply told the Flames he wouldn’t be signing long-term, which left them with the choice of trading him on their own terms or losing him for nothing later. They traded him to Florida. He’s been one of the best players in the league since.
This is the modern version, and it’s arguably more ruthless than the dramatic ones. There’s no villain. There’s no incident. There’s just a player exercising leverage quietly and efficiently.
What Larkin’s Request Says About the Yzerman Rebuild
Steve Yzerman has been Detroit’s general manager since April 2019. That’s seven years. The Red Wings have missed the playoffs in every one of them, extending a streak that now sits at ten consecutive seasons.
This is no longer the early Yzerplan. There have been real pieces added – Moritz Seider, Lucas Raymond, a legitimate young core. The case for patience was always reasonable. But Larkin has apparently stopped making it, and he’s the one who was supposed to be living it.
That’s what makes this harder than a normal trade request. Larkin was the bridge. He was there when the playoff streak ended, stayed through the teardown, signed the extension, wore the C through all of it. If he’s looked at the rebuild from the inside – the drafts, the development, the cap work, the coaching change – and decided the timeline doesn’t match his prime anymore, that’s not just a personnel problem. That’s a signal.
Yzerman’s reputation buys him more goodwill in Detroit than almost any other executive would get. That’s still true. And his track record of previously building a winning franchise certainly has bought him both time and patience. But seven years in, the organization isn’t being judged on prospect rankings anymore. It’s being judged on whether the best players in the room believe the team is close.
Larkin, apparently, doesn’t. So who does?
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