The Best and worst moves by the Toronto Maple Leafs this offseason

So what have the Maple Leafs done well and not so well in this offseason?
Apr 22, 2024; Boston, Massachusetts, USA; Toronto Maple Leafs center Auston Matthews (34) celebrates with his teammates after scoring a goal against the Boston Bruins during the third period in game two of the first round of the 2024 Stanley Cup Playoffs at TD Garden. Mandatory Credit: Brian Fluharty-USA TODAY Sports
Apr 22, 2024; Boston, Massachusetts, USA; Toronto Maple Leafs center Auston Matthews (34) celebrates with his teammates after scoring a goal against the Boston Bruins during the third period in game two of the first round of the 2024 Stanley Cup Playoffs at TD Garden. Mandatory Credit: Brian Fluharty-USA TODAY Sports / Brian Fluharty-USA TODAY Sports
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Worst Move: The Three-Year Extension for Goalie Joseph Woll

With the Leafs moving on from Ilya Samsonov following the 2023-24 season, Woll undeniably was expected to take over the team’s starting goalie role for 2024-25.

To show that the organization was committed to making that transition, Woll was given a hefty three-year, $10.98 million contract extension back in early July.

Despite a small sample size, Woll has surely shown that he was capable to play at an elite level whenever he minded the crease. In fact, the stability he is able to provide in net reminded many Leafs fans of the Ed Belfour and even Curtis Joseph days. So his huge bump in salary and years of commitment were well-deserved right?

However, the key part was exactly that, he was amazing whenever he ACTUALLY played. Despite being with the Leafs for parts of the past three seasons, he has been met with injuries for a fair chunk of that tenure.

In particular, Woll missed almost three critical months last season with a high ankle sprain, and once again fell to an injury in the playoffs when the team needed him most for the deciding Game 7 against the Boston Bruins. Until he can prove that he is no longer injury-prone the massive investment that the Leafs have already made in him certainly comes with a huge risk that might not end up paying off.

There is also the other end of the spectrum to consider. The Leafs have overpaid Woll on the basis that if they are right, they get some very reliable, very cheap goaltending. The problem though, is that the contract doesn't run long enough to make the potential payoff high enough. If the Leafs are right and Woll is successful, they'll only get three cheap years but you could argue that they should have gotten more potentially cheap years to make the bet worthwhile.