Kyle Dubas may not admit that he misses the Maple Leafs but he's building his own version and two key pieces are going to determine if it's a success or failure.
The Toronto Maple Leafs have been through a few different leaders in their organization over the past decade, with Brendan Shanahan leading the Presidency role while guys like Brad Treliving and Kyle Dubas were brought in as GMs to settle things down.
Their tenures were a mixed bag to say the least, and while Dubas never got as far as he hoped, the Maple Leafs were certainly a lot more exciting and fun to watch. Moving onto Pittsburgh however has given him new life, and with a roster filled with Hall of Famers and up and comers - he's got things under control.
But he's also not shy about bringing in some old friends as there have been several Maple Leafs executives who have followed him to Pittsburgh, and he hasn't been scared to trade for former players like Connor Dewar and Conor Timmins.
Nick Robertson is receiving the runway he never got in Toronto
He continued that trend this summer with the acquisitions of both Nick Robertson for the lineup and Brandon Pridham for the front office.
Robertson has a chip on his shoulders and is going to get a lot more opportunity with the Penguins meanwhile Pridham is the salary guru who helped manage Toronto's finances so he'll be crucial in contract negotiations going forward.
First let's focus on Robertson, someone who no doubt is going to get a lot more attention than Pridham. Robertson, 24, has been at the centre of trade speculation for a couple of years now, and with the team never really letting him run with things - the writing was on the wall.
Despite a career year in 2025-26 with 16 goals and 32 points, he didn't show a lot of improvement or at least enough to slide into a top-six role, and with a new onus on defence and toughness; he was expendable.
Pittsburgh needs scoring help and Dan Muse will have no issues throwing Robertson out with guys like Crosby and Malkin.
Look at how good Ben Kindel was in his rookie year, and the Penguins trusted his talents and it paid off. They are hoping for the same with Robertson, and just signed him to a fairly expensive deal so hopefully there's no buyer's remorse.
Brandon Pridham gives Kyle Dubas his most trusted front office partner
The move that didn't get as much fanfare but is equally as important is Pridham's hiring. The two go way back as Pridham was here even before Dubas, and he was his go-to guy for years when it came to managing the Core Four.
In Pittsburgh, Crosby and Malkin are free agents in 2027 so getting them re-signed if they aren't retiring is going to be Pridham's first task.
The team has a ton of free agents and expiring deals coming up next summer so Pridham will need Dubas' guidance on who is worth keeping and where the money will fit. If guys like Erik Karlsson aren't going to be re-signed then Dubas has to be vocal sooner than later - and already have a plan for next year.
They also have Jason Spezza working alongside them, so there's even more Maple Leafs connection there. It's obvious that Dubas prefers the people he trusts over even some of the better minds in the game and Pridham's hiring is objective proof.
As soon as he was gone, Dubas already had him on the phone and wanted him by his side once again - not a bad idea all things considered.
Who was the biggest loss for the Maple Leafs?
Also read on Hockey Patrol :
Former Toronto Maple Leafs forward Eddie Joyal dies at 86