The Maple Leafs' draft pick situation is a ticking time bomb that most fans don't fully understand

It's that pick though that could cause a lot of headaches going forward for the Maple Leafs, as there is a condition attached to it that could lead to Toronto losing three first-round picks.

Right now, Toronto sits last in the Atlantic and currently 25th in the NHL which would put them in line for the 7th pick if odds were 100%. If they want to save the pick they traded to Boston in the Brandon Carlo deal, they need to make sure they finish within the bottom-five.

If they get unlucky and get 6th or 7th, that pick is Boston's for the taking and Toronto is left empty-handed. It's the price you pay for trying to improve ahead of a playoff push and there's always a risk of losing your ability to draft.

Speaking of, they might not be able to draft in 2027 either.

The team sent a 2027 first to Philadelphia in the Laughton deal, and that's Top-10 protected, so if Toronto somehow becomes competitive but not enough to reach the postseason -- another pick gone.

But there's a lot of math to go on so let's break it down.

- If Toronto's pick is Top-5 protected in 2026: Toronto keeps 2026 pick, gives Boston 2027.
- If Toronto is outside Top-10 in 2027: Philadelphia receives 2027 pick, Boston receives unprotected 2028 pick.
- If Toronto is Top-10 in drafting in 2027, they can choose to give Boston the 2027 pick to complete the Carlo deal and give Philadelphia the 2028 pick or
- Choose to give Philadelphia the 2027 pick, and Boston the 2028 pick.

As complicated as it is, there looks to be an incredible amount of luck involved and a lot of it depends on how this season ends up.

There is a positive out of all this though, as Toronto still owns a 2027 first-round pick thanks to the Nic Roy deal. Granted, it's conditional based off a Top-10 finish for Colorado though it's hard to imagine them free-falling like the Maple Leafs.

But it's still a negative differential as it's one pick in, three traded away and for a rebuilding team having a lack of assets to either draft with or deal from will turn a short retool into a longer rebuild.

Best case scenario: Toronto finishes Top-5, drafts Gavin McKenna, Boston drafts in 2028, all parties happy with the result.

Worst-case scenario: Toronto finishes outside the Top-5, loses their pick to Boston, compete just enough to finish outside the Top-10 in 2027 and lose the pick to Philadelphia or Boston, and pay the other team the 2028 pick.

Boston also ends up with a potential franchise-changing player meanwhile Toronto gets two seasons of mid-level play from Carlo.

Toronto is going to be praying for the former, because it's a chance for them to seriously accelerate a retool, but if they fall short in the luck department it could be a long time before they win, and draft in the first round.

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