The Montreal Canadiens are the most successful team in NHL history, boasting 24 Stanley Cup victories, yet they have not won the championship since 1993. Their past success is shadowed by recent performance declines, attributed to poor recruiting and tactical flaws. The Toronto Maple Leafs closely follow with 13 titles but similarly suffer from a long championship drought since their last victory in 1967, punctuated by a string of early playoff exits. Both teams aim to revitalize their legacies in the ongoing playoffs, facing significant challenges ahead.
The Montreal Canadiens lead with 24 Stanley Cup wins, yet their last victory was in 1993, struggling for success amidst a long championship drought.
The Toronto Maple Leafs have secured 13 Stanley Cup titles but havenât won since 1967, consistently underperforming in the playoffs since 2017.
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