The Toronto Maple Leafs have had many players come through the organization that leave and find success elsewhere. For some, leaving was their own choice. For others, they either got traded or were not re-signed due to salary cap restrictions.
The Toronto Maple Leafs have been operating with a limited amount of salary cap space since signing team captain John Tavares to $11 million a season for seven years back in 2018, although it hasn't seemed to hurt them much.
That said, having Tavares, Auston Matthews, and Mitch Marner all making over $10 million a season has made it tricky to keep other players. William Nylander's new contract ($11.5 million) begins next season, as does Matthews' new deal ($13.25 million). Soaring contracts make it hard to keep everyone happy. (Salary cap info from capfriendly.com)
Sometimes, players are well-liked internally by the players, coaches, and management but need to be traded for the team to try and improve.
Other times, players have a much different opinion of how much they're worth than the Leafs do, and therefore, the Leafs are unable to sign them, and they sign elsewhere. It is all just part of the business side of sports. Even more so with a hard salary cap like in the NHL.
As a fan of the Leafs, I wish most players the best of luck when they leave. I understand that it isn't always their choice to leave. Seeing them find success elsewhere is nice, so long as it's not against the Leafs. I thought it would be fun to look at a few former Leafs and see how well they're doing on their new team.