William Nylander’s name has been tossed into trade chatter plenty of times during his run with the Toronto Maple Leafs, but nothing ever actually happened. Still, there was apparently a moment in 2021 when a move felt a lot closer than most people knew.
According to Maple Leafs superfan and content creator The Hockey Illuminati, Toronto seriously considered a proposal from the Philadelphia Flyers that would have sent Nylander to Philly for Travis Konecny and a draft pick.
“I was talking with a friend of a friend over the weekend. This guy works very closely on the Amazon Prime documentary about the Leafs back in 2021.
He was telling me that they were essentially following the team around 24/7 for a full year. They had a ton of footage and a lot of it didn’t make it into the series.
One of the more interesting scenes that was deleted for obvious reasons was a very heated spicy debate between the brain trust of Kyle Dubas, Brendan Shanahan and Sheldon Keefe about whether or not they should accept a trade Philly had just proposed to them which was Konecny and a draft pick for Nylander. Shanahan wanted to do it, Dubas did not want to do it, and Keefe was in the middle.
Ultimately, they all couldn’t get on the same page and they passed. But apparently it was this close to happening.
Travis Konecny for Nylander,”
If that account is accurate, it would have been a massive swing for both clubs. Toronto would have moved one of its most recognizable forwards, while Philadelphia would have landed Nylander in a deal that clearly got real enough to spark a major internal debate.
The twist is that both players later ended up staying put on long-term deals. In 2024, Nylander signed an eight-year, $92 million extension with the Maple Leafs, and Konecny followed with an eight-year, $70 million contract from the Flyers.
Nylander’s 2020-21 season wasn’t his strongest, but what came after was. He put together the five best seasons of his career following that shortened campaign, which makes the Leafs’ decision to hold onto him look even better in hindsight.
And while Toronto still hasn’t found the playoff breakthrough it has been chasing, the idea of that almost-trade opens up a different kind of what-if, including how things might have looked for Mitch Marner and whether he would still be in Toronto now.
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