Dylan Larkin, Brady Tkachuk and the Messiest NHL Trade Requests of All Time
Updated 09 Jul, 2026
Dylan Larkin’s reported trade request from Detroit remains one of the NHL offseason’s biggest unresolved stories. Sportsnet’s Elliotte Friedman first reported the request on June 4, and subsequent reports linked Larkin’s preferred destinations to the Florida Panthers, Minnesota Wild and Vegas Golden Knights. Neither Larkin, his agent Pat Brisson nor Red Wings general manager Steve Yzerman has publicly commented on the situation.
That uncertainty is part of what makes it so striking. Larkin is 29, a Michigan native, Detroit’s captain and the player most closely associated with the Red Wings’ attempt to climb out of their rebuild. If he is truly ready to leave, this would be more than a star-player transaction. It would be a defining moment for the Yzerman era.
NHL history is full of moments like this: trade requests, holdouts, public ruptures and contract impasses that changed franchises. Some became disasters. Others became the first step toward a Stanley Cup somewhere else.
NHL Franchise Exit Timeline
From Eric Lindros refusing Quebec to Dylan Larkin reportedly asking out of Detroit, player leverage has shaped some of the NHL’s biggest franchise turning points.
Why it matters: Player exits are rarely just about one contract or one bad season. In many cases, they reveal a deeper issue with timing, trust, team direction or belief in the franchise’s plan.
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.
Lindros never actually played for the Nordiques, which makes this entry strange – but it belongs here because it was the original proof that a player could simply refuse. Quebec drafted him first overall in 1991. He declined to play for the franchise, and the dispute eventually ended with Philadelphia acquiring his rights.
The return package eventually became part of the spine of the Colorado dynasty: Peter Forsberg, Ron Hextall, Mike Ricci, Steve Duchesne, Kerry Huffman, Chris Simon and two first-round picks. Some of those assets later helped Quebec, by then Colorado, acquire Patrick Roy. So Quebec lost Lindros and, in a roundabout way, kind of won anyway. That does not make the standoff any less wild in retrospect.
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 is not a perfect parallel – Larkin’s reported situation does not appear to involve a public medical dispute or a direct personal confrontation – but the broad shape of it rhymes. Captain. Long rebuild. A player deciding his timeline may no longer match the organization’s. Then the possibility of a fresh start elsewhere.
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.
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 vetoes the trade. You cannot 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.
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.
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 was not 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 player-franchise split ends with a clean break. Sometimes it just hangs there.
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 are reported. This one you could watch happen.
No explosion. No benching. No public declaration. Tkachuk simply told the Flames he would not 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 is arguably more ruthless than the dramatic ones. There is no villain. There is no incident. There is just a player exercising leverage quietly and efficiently.
Brady Tkachuk’s departure from Ottawa is the newest and clearest example of how quickly a captain’s future can reshape an entire franchise. Tkachuk still had time left on his contract, but the Senators moved early after it became clear that his long-term future with the team was uncertain.
Ottawa traded Tkachuk to the Florida Panthers, reuniting him with his brother Matthew and receiving a significant package of draft capital in return. Senators general manager Steve Staios later confirmed that Tkachuk had requested the trade.
That is what makes the Brady Tkachuk situation relevant to Detroit. A team can have a captain under contract, a competitive roster and a public message about building forward – and still reach the point where the player’s timeline no longer matches the organization’s. Once that happens, the trade request becomes less about one player and more about whether the franchise can recover quickly enough.
Steve Yzerman has been Detroit's general manager since April 2019. The Red Wings have missed the playoffs in every one of those seasons, extending a streak that now sits at ten consecutive years.
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’s reported request has raised an uncomfortable question: does the timeline still match the prime of the player who has lived the rebuild more closely than anyone?
That is 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 and wore the C through all of it. If he has looked at the rebuild from the inside – the drafts, the development, the cap work and the coaching changes – and decided the timeline does not match his prime anymore, that is not just a personnel problem. It is a signal.
Yzerman's reputation buys him more goodwill in Detroit than almost any other executive would get. That is still true. His record of building a winning franchise has earned both time and patience. But seven years in, the organization is no longer being judged on prospect rankings. It is being judged on whether the best players in the room believe the team is close.
Brady Tkachuk shows what happens after a captain’s relationship with a franchise reaches its conclusion. Dylan Larkin may be approaching that same crossroads – but Detroit still has time to prove that this is not yet the ending.
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