Wayne Gretzky’s summer of 1996 could have taken him to Toronto. Instead, the Maple Leafs passed on the chance, and one of hockey’s biggest “what ifs” was born.
By that point, Gretzky was a free agent and had no desire to re-sign with the St. Louis Blues.
He was deep into the final stretch of his career and was looking for the team he would finish with. Toronto was one of the places he wanted to land.
His father was sick, and Gretzky wanted to be close to him. With Brantford less than an hour and a half away, the fit made plenty of sense.
The Leafs were interested too. General manager Cliff Fletcher wanted to bring Gretzky in, and it’s easy to see why.
Toronto had just suffered back-to-back first-round exits, but not long before that, the club had reached the Conference Finals in consecutive seasons. Adding Gretzky seemed like the kind of move that could snap the team back into true contender status and maybe push it all the way to the Cup Finals.
But there was a catch, and it was a big one: the Maple Leafs board of directors had to approve the deal. This was a shaky period for the franchise.
The longtime owner had died a few years earlier, the team was dealing with financial issues, and a new arena was draining resources. When the board weighed the cost, it shut the idea down.
That decision sent Gretzky elsewhere. He signed a three-year deal with the Rangers and produced 57 goals and 192 assists for 249 points in New York. He also helped the Rangers reach the playoffs in 1996-97.
Those are the kinds of numbers Toronto could have used. The Leafs could have had a boost in 1996-97 and 1997-98, and maybe even a different outcome against the Sabres in the 1999 Eastern Conference Finals.
Instead, Gretzky’s near-move to Toronto remains one of the biggest what-ifs in franchise history. If the board had approved the money, or if Fletcher had gotten the green light, Leafs history - and Gretzky’s late-career path - might have looked very different.
In Other News...
Maple Leafs Face A Blue Line Debate Fans Know Too Well
Logan Stanley is the kind of defenseman that tends to split opinion quickly, and the Maple Leafs are again staring at a blue line question they know all too well. His size is obvious, and so is the appeal for a team that has sometimes looked for a little more edge on the back end, but Toronto has spent so much time building around speed and puck movement that any discussion of Stanley has to start there.
If the Leafs were to take a run at him, it would almost certainly have to be on a low-risk basis and with a limited role in mind. Even then, there is no guarantee Toronto decides the fit is worth it, which is part of what makes this feel like such a familiar debate for a club that keeps weighing physicality against the way it wants to play. [Read more 🡒]
Gavin McKenna Is Getting The Maple Leafs Support Every Prospect Needs
The Maple Leafs are setting up Gavin McKennas arrival the way a franchise hopes to handle a prized young player: with a development path built around proven voices and a clear plan for the transition to the NHL. McKenna is expected to work with trainer Andy OBrien and strength coach Jason Martin, two names tied to the same Pittsburgh development model that helped shape Sidney Crosby, which gives Toronto a familiar blueprint as it prepares for a prospect with big expectations.
Auston Matthews will also be part of that support structure, giving McKenna the kind of veteran mentorship that can matter as much as any workout or skill session once a young player reaches the league. The Leafs know the adjustment is about more than talent alone, and the goal is to make McKennas debut feel less like a leap into the unknown and more like a carefully managed step into the NHL. [Read more 🡒]