The 2025-26 NHL season opens this week with one overriding issue: Connor McDavid. Will the best player in this generation stay in Edmonton or go elsewhere? It’s a question that will be asked every day till the playoffs end or McDavid is traded. Naturally Edmonton is having a meltdown. Some are resigned to losing him. Others feel he could sign a bridge deal.

When it comes to losing their stars, Oilers City has been there before. The trade that always gets top billing is the 1988 Gretzky deal to the L.A. Kings, the seismic re-organization of hockey in the late 20th century. Less talked about— but more impactful on the ice— was a trade made this week in 1991 that sent Mark Messier to the New York Rangers. Messier led the Rangers their first Stanley Cup in 1994— their first since 1940. Gretzky never won a Cup away from Edmonton.

Here’s how Messier described the deal in our most recent book Deal With It: The Tales That Stunned The NHL & Changed Hockey:

“Calling up GM Glen Sather a couple of months after the 1991 postseason ended to tell him he wanted to move, Messier years later recalled “phoning him was a tough thing. I think it was mid-July. I’d been thinking of this for a while. It wasn’t just the money. I’ve made it clear their offer was pretty good. Certainly enough, where I’d never have to worry again… But I had a gut feeling I wanted to make a change, to go. To try for a new challenge and grow a bit.”

Both sides knew it was just business of course. Messier was correct in assuming he would not enjoy anything close to a sixth Cup if he stayed for a lucrative offer in Edmonton.

“I was delighted with Mark,” Sather would admit about the parting of ways. “He’s a terrific guy to be with and a great player, and it’s sad for me to have to trade him. But it becomes more complicated than that, because of what we’re trying to do here now. I don’t want to be caught in a situation where we’re going to be struggling for five or six years, depending on the draft to get us competitive again. If you analyze the way teams in this league have worked, they’ve all run on cycles. You peak for three or four years, and then go downhill and try to get back up again. And if you don’t trade players you can recover with, then you’re never going to recover. You only have so many assets to make deals with.

Neil Smith, the Rangers general manager who had seen his team endure back-to- back playoff disappointments (beaten both times by the Capitals), got wind of the possibility of landing the great “Moose” over the summer that year. Haggling for weeks toward an eventual deal, Sather would later point out the discrepancies between markets that were tearing apart the NHL at that time, bemoaning that “Maybe they’ll pay (Mark) in New York, maybe Mark is the kind of guy that can attract enough attention to do that. I mean, he’s going to be the matinee idol, he’s Madison Avenue, he’ll be terrific there. He’s the first big superstar they’ve had since Rod Gilbert, so they can afford to pay him whatever they want to pay. We don’t have MSG behind us.”

Edmonton’s training camp in 1991 went on with Messier absent, while he headed to Hilton Head to play golf with his father and brother following the 1991 Canada Cup win. Messier’s sabbatical in the sun ended on the day Edmonton’s season had started. On October 4, 1991, Messier got the call on the 16th tee box at Palmetto Dunes in South Carolina. It was Sather telling him he was headed to Broadway. In the deal, Bernie Nicholls, Steven Rice, Louie DeBrusk and future considerations (completed when the Rangers snagged Jeff Beukeboom for David Shaw) would be coming over in exchange for the vaunted Oiler captain. In the aftermath, an elated Smith hyperbolically called it “the biggest day in the 66-year history of the New York Rangers.” Hundreds and hundreds of miles away to the Northwest, reactions were considerably less enthusiastic.”

The rest was legend. With the media pressure and criticism mounting in the 1994 Conference Final, Messier was asked before the pivotal Game 6 matchup if he guaranteed a win. Responding, “Yes, we will win tonight,” he made what seemed like an innocuous comment at the time. But it was used by a NYC sports media that still lionized when “Broadway” Joe Namath had guaranteed his Jets would pull off the upset of the Baltimore Colts in Super Bowl III in 1969. Newspaper headlines honed in on Messier’s “bold guarantee.” The bravado would fall flatter than a pancake if this bulletin-board quote instead got the Rangers eliminated. Instead, Messier’s performance solidified his legacy as one of the great leaders/captains the sport had ever seen.” And the Rangers carried off the Cup, besting longtime whipping boys Vancouver in seven games.

Will McDavid win a Cup in Edmonton in 2026? Will he, like Messier, get his Cup with a large market team? Or will he be like Gretzky, doomed to play for three more teams without the big prize? This week we start the engines on Edmonton’s worst nightmare.

Bruce Dowbiggin @dowbboy is the editor of Not The Public Broadcaster A two-time winner of the Gemini Award as Canada's top television sports broadcaster, his new book Deal With It: The Trades That Stunned The NHL And Changed hockey is now available on Amazon. Inexact Science: The Six Most Compelling Draft Years In NHL History, his previous book with his son Evan, was voted the seventh-best professional hockey book of all time by bookauthority.org . His 2004 book Money Players was voted sixth best on the same list, and is available via brucedowbigginbooks.ca.

between markets that were tearing apart the NHL at that time, bemoaning that “Maybe they’ll pay (Mark) in New York, maybe Mark is the kind of guy that can attract enough attention to do that. I mean, he’s going to be the matinee idol, he’s Madison Avenue, he’ll be terrific there. He’s the first big superstar they’ve had since Rod Gilbert, so they can afford to pay him whatever they want to pay. We don’t have MSG behind us.”

Edmonton’s camp had gone on with Messier absent too, while he headed to Hilton Head to play golf with his father and brother following the Canada Cup win. Messier’s sabbatical in the sun ended on the day Edmonton’s season had started. On October 4, 1991, Messier got the call on the 16th tee box at Palmetto Dunes in South Carolina. It was Sather telling him he was headed to Broadway. In the deal, Bernie Nicholls, Steven Rice, Louie DeBrusk and future considerations (completed when the Rangers snagged Jeff Beukeboom for David Shaw) would be coming over in exchange for the vaunted Oiler captain. In the aftermath, an elated Smith hyperbolically called it “the biggest day in the 66-year history of the New York Rangers.” Hundreds and hundreds of miles away to the Northwest, reactions were considerably less enthusiastic. Sather tried to put a happy face on his new look, budget-minded lineup, insisting “I know we have a lot of past first-round picks with a lot of talent. How they work together and how they fit in our team is going to be complicated, and it takes a while to put that together, but we’re virtually back where we were 10 years ago – with a lot of young talent, and a huge upside… Whether we’d be better with Mark than with the other three guys -– I can’t speculate on that. I think we’ll be a better team in the long run, and maybe even by Christmas, I don’t know.” Sadly, for all involved on the Edmonton side, Sather’s optimism would not be rewarded.

The McDavid Dilemma: Edmonton Faces Another Big Mess