The NHL trade deadline often comes with a dizzying number of trades and transactions. The moves may also come with specific conditions attached. Some of those conditions can come back to haunt teams.
That could be the case for the Philadelphia Flyers. When Philly traded Scott Laughton at last year’s deadline to the Toronto Maple Leafs, the move was widely questioned on Toronto’s end. The Leafs surrendered a first-round pick plus a prospect, Nikita Grebenkin, in exchange for the veteran center.
But what escaped most fans and observers is that the first-round pick was a conditional pick. Therein lies the dilemma.
Let’s now add another layer of complexity. Also, during last year’s deadline, the Leafs traded a first-round pick for defenseman Brandon Carlo.
Okay, so these are separate deals. Then, what’s the problem?
It just so happens that in the Carlo trade, the Maple Leafs sent a conditional 2026 first-round pick for Carlo. The condition is that the pick is top-10 protected. In other words, if the Leafs’ 2026 pick lands in the top 10, they get to keep it.
To compound the matter, the Leafs are currently slated to pick 10th. The NHL Draft Lottery could make the pick even higher, allowing the Maple Leafs to keep it.
If the Leafs keep their pick, the Bruins get Toronto’s 2027 first-round pick, the one pledged to the Flyers in the Laughton trade.Â
Oh, but that’s not all. Since that unprotected 2027 first-rounder has been pledged to two teams, the Leafs hold the right to decide who gets it. The Leafs could choose to give it to the Bruins, handing the Flyers a 2028 first-round pick. Likewise, the Leafs could give the 2027 pick to the Flyers and give the Bruins a 2028 pick.
That 2027 pick is unprotected, and that’s where the Leafs could actually squeeze both the Flyers and Bruins.
Flyers could bid for a high first-round pick in 2027
If we assume the Maple Leafs have a banner year in 2027, it really wouldn’t matter who gets the pick. It would be a late first-round pick. So, the sting of losing it wouldn’t be that bad.
But what if the Maple Leafs continue to spiral downward? What if that 2027 unprotected pick ends up being a top-five pick? How would that change the dynamics of the Leafs’ decision?
If Toronto wanted to go for the jugular, they could pin the Flyers and Bruins against one another for the pick. The Leafs could turn around and ask for additional assets, or perhaps take back a toxic contract, just for the privilege of being the team they choose to hand that 2027 pick.
The Flyers could, of course, just sidestep the issue and let the Leafs and Bruins pay up for the pick. But what would fans think if the Flyers did nothing to land a top-five pick? Would leaving a pick like that on the table sit well with the fan base?
It’s a complex matter that could unfold an intricate web of backdoor negotiations. Perhaps the best thing that could happen to the Flyers is for the Leafs to make the playoffs this season, hence making this entire conversation moot.
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