Ranking Maple Leafs possible draft lottery scenarios

It’s finally draft lottery day. We now know that it will be John Chayka making the pick if the Toronto Maple Leafs own their first round after Tuesday. Who of the current Hockey Operations department will be involved remains a mystery, but the next couple of weeks will see those details ironed out as well.

As for the Maple Leafs’ possible outcomes, here are the best to worst outcomes for the Maple Leafs.

Drafting options:

Best case scenario (Picking first):

The Maple Leafs win the draft lottery. That’s a no-brainer for the best-case scenario and gives the Maple Leafs their choice between Gavin McKenna and Ivar Stenberg. Odds are McKenna is the preferred outcome, and that goes a long way to improving the Maple Leafs lineup in need of another elite forward.

Next best case scenario (Picking second):
The Maple Leafs wind up with the second overall pick and take whichever of McKenna and Stenberg is left. Still a pretty solid outcome and does most of the things that getting the first overall would without the added pressure of making the right selection between the top two draft eligibles.

It’s probably good, but… (Picking fifth):
If the Maple Leafs don’t win the draft lottery but no team currently slated to pick behind them wins either, the Maple Leafs will retain the fifth overall pick.

The consensus rankings say that they should select a defenceman there. The Maple Leafs need help on defence, but the player is unlikely to offer the immediate help the Maple Leafs need. They could still take a franchise defenceman here, or they could reach for a forward they believe is NHL-ready to upgrade their top six, but likely not at the McKenna/Stenberg level.

The additional downside is that the Leafs would be seeing their 2027 pick transfer to the Bruins and their 2028 pick transfer to the Flyers. The risk here is that the 2027 pick, if the Leafs don’t make a selection this year, is top ten protected. There is a chance that the Leafs might have the opportunity at someone better available in 2027 than is available at 5th overall in 2026.

At least the Bruins pick is a little worse (Bruins pick seventh):

If two teams leapfrog the Maple Leafs and the Bruins select 7th, the Maple Leafs at least gave the Bruins a slightly lower pick than 6th.

Bummersville (Bruins pick sixth):
Giving the Bruins the sixth overall pick. It’s not Brandon Carlo’s fault, but man, will that guy need a change of scenery if he’s associated with the Leafs giving up a sixth overall pick and Fraser Minten for him.

Trading Options (not relevant to the draft lottery, but if the Leafs retain their 2026 1st round pick):

Best case scenario:
The Leafs trade the fifth overall pick for a young NHL player who can help them win now. The Leafs probably shouldn’t keep trading high-end draft picks, but if they are capable of getting a win here, it might be worth it. Counterpoint: Trading the pick for a 30-year-old veteran presence would probably be the worst of the worst-case scenarios.

Best case scenario 1B:
Packaging the fifth overall pick with another piece to move up in the draft to go after McKenna or Stenberg would be the best of both worlds. They could get a high-end young talent and move a roster player who might not be a fit in the current lineup. It’s just a matter of crossing your fingers that one of the top two teams in the draft lottery really needs a defenceman.

Okay…:
Trading down from fifth overall. The Leafs don’t necessarily need to pick a defenceman at fifth overall, and if they want to pick up an additional asset or two and then take a solid forward prospect, that would be tidy business (that likely wouldn’t be well received)

Worst-case scenario:
Trading either the first or second overall. If this franchise receives the gift of a lottery win and then wastes it, the inevitable Maple Leafs square riot will be justified.