During the summer of 2021, the Toronto Maple Leafs chose not to extend first-line winger Zach Hyman. Instead, he signed a free-agent deal with the Edmonton Oilers and joined superstar Connor McDavid.
Let's be clear. At the time, the Toronto Maple Leafs made the right decision. Hyman was a hard-working player, capable of helping offensively, and also killed penalties, but the Leafs had more pressing needs.
Hyman's career-high in goals was twenty-one, and he fought injuries. He was 29 years old at the time and his style of play was conducive to more potential injuries. Handing out long-term contracts to aging, non-superstar players in a salary-cap era is not a recipe for success.
A player entering his 30s, with known knee injuries, with a career high of 21 goals and 41 points, who wants to double his salary and is asking for a commitment until age 36 does not warrant the contract the Oilers gave him. Yes, he earned it, but he did so by defying everything we know about aging in the NHL, let alone assumptions about play-style and injuries.
The Leafs needed to be mindful of having enough space to sign Auston Matthews, William Nylander, Mitch Marner, and Morgan Rielly. They couldn't be faulted for choosing not to match the Oilers offer, but what Hyman has done since must make the Leafs regret the decision.
Though, keep in mind this as well: When the Leafs let Hyman walk, they signed Michael Bunting for 5x cheaper and for two seasons he posted franchise-level numbers besides Auston Matthews and Mitch Marner at 5v5. His two seasons in Toronto were statistical superior (if not as beloved) to any of Hyman's best seasons as a Leaf.
Hyman has been so good in Edmonton that the Leafs actually regret not signing a 30 year old with bad knees despite replacing him with a superior player (at least compared to what each player did n a Leafs uniform) for 5x less money.