Operation ‘Appease Auston Matthews’ is in full swing. Signing Raddysh, arguably the top UFA defenseman on the market, through a June sign-and-trade that pays him for eight seasons beginning at age 30 erased any doubt that Toronto wants to stay competitive as long as Matthews remains with the team. The Leafs stayed incredibly aggressive in the UFA market Wednesday. Bobrovsky represents their highest-profile goalie gambit since Ed Belfour more than 20 years ago; it remains to be seen what future Hall of Famer ‘Bob’ has left, turning 38 in September, but he’s only a year removed from back-to-back Stanley Cup wins, and the three-year contract term isn’t too prohibitive.

Adding Jack Roslovic, a.k.a. Matthews’ old linemate at USA Hockey’s National Team Development program, and Colton Sissons, a versatile bottom-six center who wore many hats in the lineup for the Vegas Golden Knights during their run to the 2025-26 Stanley Cup Final, along with checking pivot Teddy Blueger and speedy Brandon Duhaime, deepens the forward group. Once you factor in the trade for analytics darling defenseman Emil Andrae last month, dealing goalie and surplus asset Dennis Hildeby for third-line center Nick Paul Wednesday and, of course, picking Gavin McKenna first overall in the 2026 Draft: the Leafs are an improved team year over year coming out of July 1 – most notably in their foot speed. Will their current path prove to the be the wrong one? Perhaps, as the Leafs’ contention window may have closed already, and this team is so radically different now that chemistry won’t necessarily come easily.

But on the other hand, GM John Chayka may have cranked the window back open, which he had no choice to do with Matthews and fellow veterans such William Nylander, John Tavares, Matthew Knies and Chris Tanev under contract. The time to rebuild is if and when Matthews walks away, whether that’s in 2028 when he’s a UFA or a year from now when he’s extension eligible. But the time is not now, and the Leafs deserve credit for taking extremely decisive steps to reload and reinvent. You have to go all in as long as you have No. 34, and it’s worth noting most of the deals Chayka handed out were short-term, Raddysh’s excepted.