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The story behind Toronto's failed pursuit of Wayne Gretzky in 1996

April 18, 1999; New York, NY, USA; New York Rangers' Wayne Gretzky waves goodbye after his final hockey game. Mandatory Credit: Robert Deutsch/USA TODAY NETWORK
April 18, 1999; New York, NY, USA; New York Rangers' Wayne Gretzky waves goodbye after his final hockey game. Mandatory Credit: Robert Deutsch/USA TODAY NETWORK | USA TODAY Network via Reuters Connect

When the Edmonton Oilers traded Wayne Gretzky to the Los Angeles Kings, it was a national tragedy for Canada. They were sending the best player ever to play the country’s favorite sport to their southern neighbor. It was a move that drew the anger of not just Oilers fans, but Canadian hockey fans everywhere.

What made it worse is that The Great One would never play another game for a Canadian team. But things could have been different if the Maple Leafs had made a bigger push to sign him in 1996. But how did the Leafs let Gretzky get away?   

How the Maple Leafs missed out on Wayne Gretzky

In the summer of 1996, Gretzky was a free agent and had no interest in re-signing with the St. Louis Blues. He was entering the twilight of his career and was looking for the team he would retire with. One of the teams he was interested in signing with was the Toronto Maple Leafs. His father was sick, and he wanted to be close to him. With Toronto being less than an hour and a half drive to his hometown of Brantford, it seemed like a perfect fit.

It was not just Gretzky who liked the idea of playing with the Leafs. Cliff Fletcher, the Leafs general manager, was very interested in signing him. The Leafs were just coming off back-to-back first-round exits. They were also just a few seasons removed from making back-to-back trips to the Conference Finals. The thought was that adding Gretzky could be the jolt the roster needed. He could be the missing piece to get them back to the Cup Finals.

While Gretzky and Fletcher were on board, there was one more party that needed to agree: the Maple Leafs board of directors. This was one of the most uncertain times in Leafs history. The long-time owner had passed away a few years earlier, and the Leafs were having money problems. On top of that, they were also building a new arena, which ate most of the available resources. The board rejected the idea of going after Gretzky, citing that the move would be too expensive.

With the move nixed, Gretzky ended up signing a three-year deal with the Rangers. Over his time on Broadway, he logged 57 goals and 192 assists for 249 points. He also helped the Rangers make the playoffs in 1996-97. This is the type of production that the Leafs could have used during this stretch. It could have helped them make the playoffs in 1996-97 and 1997-98. It also could have given them the extra push they needed to get past the Sabres in the 1999 Eastern Conference Finals.

Gretzky not signing with the Leafs will go down as one of the biggest what ifs in team history. If the Leafs had the money or the board gave Fletcher his blessing, who knows how Leafs history and Gretzky's legacy might have changed.

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