How they will be remembered
There's no denying that from the moment Matthews became a Leaf, it was an exciting time to be a fan of this team. The team showed promise of many deep playoff runs and had multiple highly skilled young players who became fan favorites instantaneously.
Unfortunately, the hype didn't match the success, and to be blunt, all this core will be remembered for, other than two measly first-round wins, is their regular season success. They'll also be remembered for being incredibly greedy, as they tried to squeeze every penny out of management.
Yes, some of it can be faulted on the players as they chose wealth over success on the ice, but it's also management's fault for handing out multiple lucrative deals to young, unproven players for their first contracts.
It's a big reason Shanahan will likely be gone this off-season. He's the one who elected for an inexperienced Dubas who failed to effectively negotiate with Toronto's then-young stars by giving them deals that will forever be benchmarks for years to come and will hamstring management. It's part of why they might not have any choice but to let Marner walk in free agency this summer.
It's Shanahan who gave the green light to Dubas to hire an inexperienced head coach in Keefe, who had no prior experience coaching in the NHL playoffs, where he would be coaching a team with a troubling track record of post-season success. Keefe's inexperience showed at times as he let the tense playoff atmosphere get to him, further passing on that energy to his already scarred players.
Shanahan could've retooled this core many times, especially after their 3-1 choke to the Canadiens in 2021, which clearly showcased multiple seasons in a row that this core didn't have what it took to win a playoff series. Instead, Shanahan stuck with the group while giving up a big portion of assets along the way.
The definition of insanity is doing the same thing over and over again and expecting different results. The Shanaplan fits that definition to a tee, which is why its founder should pay the price of a nine-year heartbreak, and you can bet that decision starts with Keith Pelley, the CEO of Maple Leafs Sports and Entertainment, who returned from being the Cheif Executive of the European Golf Tour just last year.