While the team was very good last season, ultimately it was a season filled with ups and downs that ended with a first-round loss to an excellent Boston Bruins team. It wasn’t a failure of a season, but since signing Tavares, things have not exactly gone smoothly for a team that should be in the middle of a Cup window.
As their 2018-19 season progressed, it began to be overshadowed by a contract dispute between Leafs management and William Nylander. Eventually, Nylander did return, but having missed the first few months, he was nowhere near his prime form.