#7. Joe Nieuwendyk
The signing of Nieuwendyk is one similar to Marleau.
Although Marleau’s career wasn’t as decorated with Stanley Cup’s as Nieuwendyk’s was, in both instances, the Leafs were signing a Hall-of-Fame veteran trying to get a last chance at winning.
When Nieuwendyk had arrived in Toronto, he had done everything a player dreams of in an NHL career. He’d won a Conn Smythe and three Stanley Cups with three different teams.
However, the only thing missing was the chance at winning a fourth Stanley Cup in his hometown.
The fondest memory of Nieuwendyk will always be during the 2004 NHL Playoffs in Game 7 against the Ottawa Senators.
Streaking through the left-wing, Nieuwendyk scored two identical goals against Patrick Lalime that secured the series win for Toronto and sent them to the second round.
Although the Leafs were unable to win the Stanley Cup in the one season that Nieuwendyk played in Toronto, he provided great leadership and was a tremendous player that season.