A longshot win in Tuesday’s NHL Draft Lottery was fantastic news for the Toronto Maple Leafs, but it created muddier waters when it came to how trade conditions will be applied to future first-round picks the team owes to the Philadelphia Flyers and Boston Bruins.

Specifically, it introduced the possibility that Toronto’s option to transfer or keep a top-10 pick in 2027 might effectively give the Leafs the chance to choose whether the Flyers or Bruins would get such a selection.

At least in theory.

There’s some overlap in the conditions included in trades made by the Leafs a couple hours apart on March 7, 2025 — the “win-now” deals that brought in Scott Laughton and Brandon Carlo. They were made at a time when Toronto was leading the Atlantic Division and well on its way to a ninth straight playoff berth, so it’s safe to say the people involved in negotiating the finer points of those trades had reason to believe they’d effectively become a moot point.

Whoops.

Before digging any deeper into the fine print, it’s important to note that the NHL still hasn’t formally provided an interpretation of how the Leafs’ first-round picks in 2027 and 2028 will be divided between Philadelphia and Boston.

Asked about it prior to Tuesday’s draft lottery, deputy commissioner Bill Daly told reporters: “I’m not prepared to answer that question is what I’d say. It’s a complicated situation.”

The NHL has not committed to a timeline to provide clarity.

In theory, the league could allow the 2026-27 season to play out and see where things land after next year’s draft lottery before making a determination because there’s only a debate if Toronto’s 2027 pick falls inside the top 10.

“It’s a confusing situation, but we’ll deal with it if we have to,” Daly said.

So, what exactly is the issue here?

It boils down to the wording attached to multiple conditional picks.

The first deal the Leafs completed at the 2025 deadline was the one that landed Laughton from Philadelphia. They sent back a conditional 2027 first-round pick as part of the package, which was reflected in the trade summary list distributed by the NHL to teams afterwards and obtained by The Athletic:

Philadelphia trades Scott Laughton, Philadelphia’s 4th rnd pick in 2025 NHL Draft and Philadelphia’s 6th rnd pick in 2027 NHL Draft to Toronto in exchange for Nikita Grebenkin and Toronto’s 1st rnd pick in 2027 NHL Draft. If Toronto’s 1st rnd pick in 2027 NHL Draft is in Top 10, then Toronto has the option to retain such pick and instead transfer their 1st rnd pick in 2028 NHL Draft to Philadelphia. If Toronto trades their own 2028 1st rnd pick (in a subsequent trade) prior to the 2027 NHL Draft, then the condition on 2027 pick is removed and Toronto’s own 2027 1st rnd pick shall transfer to Philadelphia. Philadelphia agrees to retain 50% of Laughton’s SPC as part of a Retained Salary Transaction (03/07/25)

Of note is the fact the Leafs negotiated the option to send their 2028 first-rounder in the event the 2027 pick landed top 10. However, they also agreed to relinquish that right if they dealt the 2028 pick away in a subsequent deal before the 2027 draft.

Keep that phrasing in mind.

The Leafs completed the Carlo trade with Boston a few hours after the deal with Philadelphia. They committed a conditional 2026 first-rounder — the pick that became No. 1 with Tuesday’s lottery win — and spelled out the conditions to account for that possibility as such, according to the NHL’s trade summary list:

Toronto trades Fraser Minten, Philadelphia’s 4th rnd pick in 2025 NHL Draft (previously acquired by Toronto) and Toronto’s 1st rnd pick in 2026 NHL Draft (conditional) to Boston in exchange for Brandon Carlo. In the event Toronto transfers their 1st rnd pick in 2026 NHL Draft to Chicago (pursuant to an earlier trade) or Toronto’s 1st rnd pick in 2026 NHL Draft is a top 5 pick, then Toronto will instead transfer their own 1st rnd pick in either the 2027 or 2028 NHL Draft to Boston (whichever of those picks is not transferred to Philadelphia pursuant to an earlier trade). Boston agrees to retain 15% of Carlo’s SPC as part of a Retained Salary Transaction (03/07/25)

Since the Leafs’ 2026 pick ended up inside the top five, they now owe the Bruins their 2027 or 2028 pick to fulfill the conditions of the trade, whichever of those picks didn’t go to Philadelphia. Straightforward enough.

Except this is where the need for interpretation comes in: As of this moment, the Flyers own Toronto’s 2027 pick — conditionally, anyway. Does that mean Boston should automatically be transferred the 2028 pick to close that loop now that the fate of the 2026 pick is known? Or does the condition in the Flyers trade still potentially apply, which would allow the Leafs to swap the 2027 and 2028 picks if 2027 became top 10?

That would create a potentially fascinating dynamic next offseason, if Toronto was left with the choice of determining whether Boston or Philadelphia ended up with a prized pick. In theory, the Leafs might be able to use that power as a way to coax a favorable return in a subsequent trade from one of those teams.

Ultimately, it will be left up to the NHL’s Central Registry to make a determination on which trade condition supersedes all.

The league has been aware of this potential issue for some time — long before the lottery balls fell Toronto’s way. The belief is the NHL will ultimately award the 2027 pick to the Flyers even if it falls inside the top 10, according to sources familiar with league-level discussions on the topic, but that determination hasn’t yet officially been communicated to the affected clubs as a final decision.

In that event, Boston would get the 2028 pick.

Once assigned, both Leafs picks will be free of conditions. They could wind up being pretty important selections depending on how quickly Toronto can turn things around under new general manager John Chayka.

And as much as this discussion might feel academic right now — the Leafs intend to return to a competitive window quickly and ideally won’t be surrendering lottery picks to intra-conference competitors — their own unlikely path to the 2026 No. 1 overall pick underscores why this matters so much.

In hockey, you never know what might happen next.