If one thing is for certain, it’s that Kyle Dubas loves his guys.

When the ex-Toronto Maple Leafs general manager left the north to take over the Pittsburgh Penguins, he brought with him several ex-Leafs both in the front office and on the ice.

Jason Spezza, who served as special assistant to the general manager in Toronto, resigned from his post and joined Dubas in Pittsburgh, where he became an assistant general manager.

Roster wise, Dubas signed numerous former Leafs that he had once acquired in Toronto during his first year in charge of the Penguins. Noel Acciari, Radim Zohorna, Marc Johnstone, Andreas Johnsson, and others marked a lengthy list of depth signings that Dubas made, establishing a decent ex-Leafs presence in Pittsburgh.

While that trend took a bit of a pause after the barrage in July of 2023, Dubas picked up some more former Leafs at the trade deadline this season back in March. Dubas made a deal with new Leafs general manager Brad Treliving to bring in Connor Dewar and Conor Timmins via trade. The latter was a defenseman that Dubas had previously acquired as Leafs GM.

That trade revealed two things: one, Dubas still likes to re-acquire players he once did in Toronto, and two, the hostilities between him and the Leafs seem to have faded away, with Treliving and the Leafs brass willing to make a deal with him, even if it was a small one.

With the end of an era now upon the Leafs faithful, there’s an open door for a ton of change on Toronto’s roster between now and October.

There’s ample opportunity for the Penguins to make a deal here and there, especially considering the Leafs could up in a bit of a cap crunch and need to move salary out.

Now I know what you’re thinking: Toronto has nearly $26 million in cap space heading into the offseason. Why would they need to clear space?

Having almost $26 million sounds like a fortune, but it’s going to run out faster than we think. That space doesn’t account for the massive raise pending RFA Matthew Knies is slated to get. It also doesn’t include a potential re-signing of UFA John Tavares, or whoever they sign to replace him.