5 years ago, the Avs and Joe Sakic were at their lowest point. An atrocious regular season saw them win only 22 games and finish 7th in the Central Division with just 48 points. For reference, the Montreal Canadiens, who finished dead last in the NHL this season, still managed to finish with 55 points. It's hard to imagine a team being any worse at hockey than this year's Habs squad. Harder still to believe that the same core is now in the Stanley Cup Finals.
Sakic did make a big move in that off season, or rather, was forced to when Matt Duchene demanded a trade at the end of the season. He was sent to Ottawa as part of a 3 way deal between the Avs, Sens and Predators. At the time, many were calling for Joe Sakic's job. Looking back, many people were wrong to do so. Two of the seven pieces the Avs got back are now key contributors for the Avs. Defencemen Bowen Byram and Sam Girard.
What followed was a series of playoff heartbreaks for what was a very good Avs team. Perennial contenders, they could never get over the hump. A first round loss, followed by 3 straight second round exits. Through all of this, Sakic stuck by his core of Nathan MacKinnon, Gabriel Landeskog and Mikko Rantanen.
Maybe the Leafs' situation isn't quite identical. The Leafs haven't been quite as lucky as the Avalanche in terms of timing. The Avs benefited massively from the timing of the Nathan MacKinnon contract. At the time, the salary cap was just $73 million. 3 years later, the cap had gone up by 8 milion dollars. In the 3 seasons Matthews and Marner have played since signing their deals, the cap hasn't gone up at all thanks to the COVID-19 pandemic. Also helping the Avs out was the fact that MacKinnon had only put up 53 points the year his ELC ended. He only truly broke out after he signed his contract paying him 6.3 million per season for 7 years. When Matthews and Marner signed, Matthews had scored 37 goals and 73 points in 68 games, while Marner had lead all Leafs players with 93 points. In my opinion, all 3 players were paid what they were worth at the time of their signings.
The Leafs now find themselves in a similar situation to the Avs. Strong regular seasons followed by playoff heartbreaks. To me, the Leafs best path forward is the same one the Avs have followed. Stick to your core, let your young defencemen develop, and trust your guys to figure out how to win come crunch time. Oh, and they should also try to add Nazem Kadri, that guy seems like he a real playoff performer.