While there is some positivity surrounding the Toronto Maple Leafs and the future of this team with John Chayka in charge and Gavin McKenna most likely coming later this month, there are some mistakes that Brad Treliving made that are going to be painful.
But at least now we have some clarity on just how painful those mistakes are going to be.
We are of course talking about the two first-round picks that Treliving coughed up for defenseman Brandon Carlo from the Bruins and center Scott Laughton from the Flyers during the trade deadline last year. Two trades that served as two primary reasons why Treliving was fired, but now the Leafs have to deal with the ramifications.
Fortunately, the Bruins were supposed to get the 2026 first-round pick but due to it being top-five protected and the Leafs winning the Draft Lottery, that got pushed to a future date. And the 2027 first-rounder was going to be going to the Flyers but now with the Draft Lottery win, that was also uncertain.
Well, now we know, finally.
Per a league source, the NHL has informed the Flyers that while they own the Maple Leafs' 2027 first round pick (Laughton trade), the Leafs still have the option to transfer it to Boston if it's in the top 10. In that event, the Flyers would receive Toronto's 2028 first rounder.
— Kevin Kurz (@KKurzNHL) June 10, 2026
According to The Athletic's Kevin Kurz, the Leafs will have the option to transfer the 2027 first-round pick if it is in the top 10 of next year's Draft. Basically, while the pick is technically top-10 protected, if it ends up being a very good pick and one of the first 10 selections of next year's Draft, it doesn't return to Toronto but instead the Leafs get the choice between sending it to the Bruins or the Flyers.
Unfortunately, the choice between the Flyers and Bruins is obvious
Now, while the Leafs have a choice, they don't really.
If next year's first-round draft pick is going to be in the top 10 -- a very good pick -- the Leafs are not going to just send that off to Boston just because. It would have to be an insane reason to hand over a division rival one of the best picks of the draft, instead of a team like the Flyers.
While they are both in the Eastern Conference of course, and they could end up drafting a player that is a thorn in the Leafs' side for the next decade, it will be automatically less painful if that player was in Philadelphia compared to that player being in Boston and being reminded of that awful deal forever.
So, no matter what happens, it feels like the likely end is that the Flyers are going to get the 2027 pick, and the Bruins will get 2028. Whether those picks are first overall or 32nd overall, that is most likely how it's going to shake out.
The good news really is that they don't have to have a scenario where they hand the Bruins a very good pick as soon as next year. And hopefully by 2028, Gavin McKenna is tearing the league apart and Auston Matthews has re-signed.
