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The Boston Bruins now face the worst-case scenario following the Maple Leafs stunning 2026 NHL Draft Lottery win.

The Boston Bruins had a special interest in the outcome of the 2026 NHL Draft Lottery. The Bruins held a claim to the Toronto Maple Leafs 2026 first-round selection.

As widely discussed here on Heavy, that pick, obtained in the Brandon Carlo trade last season, was a top-five protected pick.

At the time of the trade, no one imagined that the Maple Leafs would sink to the bottom of the standings the way they did. But it happened, and it raised a significant debate about whether the Leafs would keep their pick or send it to the Bruins.

Well, Tuesday night’s stunning victory by the Leafs, while leaving Bruins fans crying foul, now unleashes a wave of uncertainty for Boston.

The lack of clarity lies in how the conditions of the Carlo trade will unfold. For starters, the Bruins do not automatically get the Leafs first-rounder next year. In fact, it will be up to the Leafs who gets their first-round pick in the 2027 and 2028 NHL Drafts.

The situation became complex when the Maple Leafs pledged their 2027 pick to the Philadelphia Flyers in the Scott Laughton trade last season. Because the Leafs essentially pledged the same pick twice (2027), there will now be a contentious situation unfolding.

Maple Leafs to Decide Who Gets 2027 1st-Round Pick

The conditions of the Carlo trade stated that the Bruins would get the Leafs’ 2027 unprotected first-rounder if the 2026 pick was top five. That’s the case after Toronto won on Tuesday night. But the Leafs also pledged the 2027 pick to the Flyers. The conditions of that pick state that the Flyers would get the Leafs’ 2028 pick if the 2027 pick went to the Bruins.

So, case closed, right? The Bruins get the 2027 pick and the Flyers the 2028 selection.

Not so fast. The conditions of all the picks outline that the Leafs have the choice of sending the 2027 or 2028 pick to the Flyers. Meanwhile, if the Leafs choose to give the Flyers their 2027 pick, the Bruins would receive the 2028 selection.

While such a situation may seem implausible, it could very well unfold. And it would allow the Leafs to extract even more value for that pick.

Toronto Could Ask Bruins for Sweetener in Exchange for 2027 Pick

Since it will be up to the Leafs to decide who gets the 2027 and 2028 picks, the team could ask the Bruins for something in exchange. That may seem unfair, but it’s a reality that could emerge. Perhaps under the previous administration, the Maple Leafs might have honored the pledge as part of a gentleman’s agreement.

However, there is a new GM in Toronto. John Chayka, who’s not exactly the most forthright character in the business, could extract more value from the Bruins. There really isn’t much stopping him from turning around and asking Boston for a player or another pick to choose them ahead of the Flyers.

The Leafs could, in fact, start a bidding war between the Flyers and Bruins. Whoever wants that 2027 first-round pick may have to pony up to get it. The bidding war could become a real situation if the Leafs tank once and for all, and the 2027 first-rounder ends up becoming another top-five or top-three pick.

One way or another, this will be an interesting storyline to follow.