Kyle Dubas is leaning hard into familiarity in Pittsburgh, and two former Maple Leafs pieces may end up telling the whole story of how this new setup works out.
The Penguins have already become a landing spot for people Dubas knows well. He’s brought over former Toronto executives, and he’s also made moves for ex-Maple Leafs players such as Connor Dewar and Conor Timmins. This summer, that pattern continued with the addition of Nick Robertson to the lineup and Brandon Pridham to the front office.
Robertson is the more visible swing. The 24-year-old has been in trade chatter for a couple of years, and Toronto never really gave him the kind of runway that lets a young player settle in and grow.
Even after a career year in 2025-26, when he scored 16 goals and finished with 32 points, he still didn’t force his way into a top-six role. With the Maple Leafs putting more emphasis on defence and toughness, he became expendable.
Pittsburgh is betting that a fresh start changes the script. The Penguins need scoring, and Dan Muse should have no problem putting Robertson alongside players like Crosby and Malkin.
The club also clearly believes there’s something to unlock, since it signed him to what the source describes as a fairly expensive deal. Ben Kindel’s rookie season is the example they’re pointing to: they trusted his ability, and it worked.
Pridham’s arrival may not have drawn the same attention, but it could matter just as much. Dubas and Pridham have a long history together, with Pridham serving as Dubas’ trusted salary expert during the years of managing the Core Four in Toronto. That relationship now shifts to Pittsburgh, where the financial picture is about to get busy.
Crosby and Malkin are free agents in 2027, so getting them re-signed, if they are not retiring, is a major early task. Beyond that, the Penguins have a pile of free agents and expiring contracts coming next summer, which means Pridham will have plenty on his plate as he helps sort out who stays and how the money gets allocated. If players such as Erik Karlsson are not going to be brought back, Dubas will need to make that clear sooner rather than later and have next year mapped out.
Jason Spezza is also working with them, adding yet another Toronto connection to the mix. The message is pretty clear: Dubas trusts the people he knows, and Pridham is proof of that. As soon as he was available, Dubas had him on the phone and wanted him back beside him.
In Other News...
Maple Leafs Could Still Make One More Polarizing Move Up Front
Torontos offseason has already been busy under new general manager John Chayka, with several new faces added as the Maple Leafs continue reshaping the roster around their core. Even with those moves, there is still a sense that the forward group could use one more layer of depth, especially if the club wants another experienced option who can help in key offensive situations.
One possibility still hanging out there is a veteran scorer who just finished a productive season with Minnesota and brings a long playoff rsum with him. A short-term addition of that kind would give Toronto another look in the top nine and another body for the power play, but it would also be the sort of move that tends to split opinion because of what it says about the teams approach up front. [Read more 🡒]
Morgan Rielly Trade Talk Just Took A New Turn For Leafs
Morgan Riellys name is still hanging around the trade rumor mill, and San Jose has not gone away as a possible fit. Even after the Sharks brought in Darnell Nurse, there is still belief they could keep looking for a puck-moving defenseman who can help drive the power play, which is the kind of role Rielly has long filled for Toronto.
For the Maple Leafs, the bigger question is what kind of return would actually make sense if talks ever got serious. The discussion around the league has centered on NHL-ready pieces rather than a simple cap-clearing move, with names like Barclay Goodrow, Adam Gaudette and Patrick Giles mentioned as the sort of value Toronto could seek. For now, though, it remains exactly what it has been: speculation, with no confirmed trade and Rielly still very much in the picture for the Leafs. [Read more 🡒]
Leafs Missed Out On A Forward They May Not Have Fit
Vitali Pinchuks move out of the KHL had at least one familiar NHL team watching, and Toronto was among the clubs tied to the young forward as he weighed his next step. For the Maple Leafs, the appeal was obvious enough: a chance to add another player with upside, even if the fit was never going to be simple on a roster that has already been reshaped by several new additions.
Now the question is whether there ever would have been room for him anyway. Nashvilles offseason activity has already made Pinchuks path there uncertain, and Toronto faces its own squeeze with a crowded forward group and a cap picture that leaves little margin for another bet. In other words, the Leafs may have missed out on a player they were interested in, but the larger issue is whether he would have had a real lane in Toronto to begin with. [Read more 🡒]