2019-2021: Betting on the Core

In 2019, Marner and Matthews were both due for extensions, where Dubas would eventually sign them both to AAV's of 10.9 and 11.6 million dollars.
Since Nylander set the bar with his contract the season prior, Marner and Matthews pushed the hands of management to offer them deals more lucrative than Nylander's. Management folded into paying $29.4 million for the next five years to just three players without significant playoff success.
This is one of the more pivotal mistakes made by the Leafs in the Core Four era. It completely hamstrung management from building an effective supporting cast around the team for years to come.
After losing to the Bruins in back-to-back Game 7's and pressuring a 19-year-old Marner into ratting out his teammates, the Leafs opted to move on from Babcock. The search for the 40th head coach in franchise history didn't last long, as Dubas and the Leafs went with a familiar face in Sheldon Keefe.
Keefe and Dubas knew each other from their tenures as head coach and GM with the Greyhounds of the OHL and the Marlies of the AHL, where the two shared the team's success of winning the Calder Cup the year before.
Keefe's first couple of seasons as Leafs head coach might be one of the more disappointing years this core has endured. In the 2019-20 season, the Leafs would lose in playoff qualifying to the 28th-placed Columbus Blue Jackets in five games. Then, even after winning the Canadian Divison the following season, they would blow a 3-1 series lead to the Montreal Canadiens in what will go down as the Core Four's most memorable collapse.
At this point, there could have been changes made to the roster by management as the core had proven their inability to make it out of the first round but decided to commit long-term to this core without even retooling, despite showing signs of an inability to produce in the playoffs while also facing challenges of performing under pressure. With multiple playoff births and no success to show for it, pressure began to mount from management down to the players.