Maple Leafs 2027 Draft Picks: What Toronto Owes, and the One First It's Owed

The Maple Leafs 2027 draft picks situation is worse than the No. 1 pick made it look

The Maple Leafs 2027 draft picks ledger has one entry that matters and most people have forgotten it exists: Toronto is owed a conditional first-round pick from the Colorado Avalanche. It is the only first-rounder the Leafs control in the next two drafts, and it is the entire reason John Chayka has any ability to make an in-season trade at all.

Everything else on the first-round side is spoken for. Toronto's own 2027 first belongs to the Philadelphia Flyers. Its 2028 first belongs to the Boston Bruins. Winning the 2026 draft lottery and taking Gavin McKenna first overall was franchise-altering, and it also cleared the way for those two obligations to come due back-to-back. The bill arrives in June 2027.

With camp opening Sept. 17 and the Leafs projected over the salary cap, the picks are the only currency left. So it is worth knowing exactly what is in the drawer.

What Toronto owes, and to whom

The obligations trace back to two deals at the March 2025 trade deadline.

Toronto sent its 2026 first-round pick and Fraser Minten to Boston for Brandon Carlo. That pick was top-five protected. Toronto sent its 2027 first-round pick and Nikita Grebenkin to Philadelphia for Scott Laughton. That pick was top-10 protected.

Then the lottery balls came up Toronto in May 2026, and the protections did their job. The Leafs kept the No. 1 selection, and the obligation to Boston rolled forward. The result, per reporting from The Athletic's Kevin Kurz, is that Philadelphia is in line for the 2027 pick and Boston for the 2028 pick — with a genuinely strange wrinkle attached. If Toronto's 2027 pick lands in the top 10, the Leafs get to choose which club receives which year, because of the top-10 language in the Flyers deal.

That is a real, if morbid, piece of optionality. It only activates if the 2026-27 Maple Leafs are bad enough to pick in the top 10, which is not a plan. We mapped the full cascade when the league finally clarified it in June, in our breakdown of the first-rounders Toronto has mortgaged through 2028.

Carlo, for what it is worth, is no longer here either. Chayka moved him to St. Louis for two third-round picks this summer, converting a first-round pick into two thirds across 18 months of asset management. That is the cost of deadline aggression, paid in instalments.

What Toronto is owed: the Nicolas Roy pick

The one first-round asset coming back the other way came from the March 2026 deadline, when Toronto traded centre Nicolas Roy to Colorado.

The return: a conditional 2027 first-round pick and a conditional 2026 fifth-round pick. The fifth was defined as the lowest of Colorado's three 2026 fifth-rounders. The first is where it gets interesting. Colorado's 2027 first is top-10 protected. If the Avalanche's 2027 selection lands inside the top 10, Colorado keeps it and Toronto instead receives Colorado's unprotected 2028 first-round pick.

Read that again, because the protection belongs to Colorado, not Toronto. The Leafs are not shielded from a bad outcome — they are exposed to a delay. If Colorado has a disaster season in 2026-27, Toronto does not get the resulting high pick. It waits a year and takes whatever Colorado produces in 2028, unprotected.

What that pick is actually worth

Strip the romance out of it. Colorado has Nathan MacKinnon and Cale Makar under contract and has not missed the playoffs in the better part of a decade. The realistic range for the pick Toronto receives is somewhere between 24th and 32nd overall.

A late first-round pick is a useful asset. It is not a difference-maker at the deadline. Historical hit rates on picks in the 25-to-32 range put the odds of producing a regular NHL top-six forward or top-four defenceman somewhere well under a coin flip. What a late first buys you in trade is a middle-six rental or half the price of a good one.

Which brings us to the number that has been hanging over Toronto's front office for the last week.

The Evangelista price makes the problem concrete

On Sept. 2, Nashville traded Luke Evangelista to New Jersey for a conditional 2028 first-round pick and a 2028 second. Evangelista is a 24-year-old winger coming off 12 goals and 44 assists for 56 points in 81 games, on the second year of a two-year, $6-million contract.

That is a first and a second for one season of a $3-million winger who has never scored 20 goals. It is also, almost exactly, the profile of player Toronto has been trying to find for Auston Matthews' right side since the day Chayka took the job. We wrote at the time that the Evangelista trade set a price Toronto cannot pay, and the Colorado pick is why. It is one first. Spending it means the Leafs enter the 2027 and 2028 drafts with no first-round selection in either year, having already surrendered both of their own.

That is not a cap constraint or a cash constraint. It is a structural one, and it does not resolve until the 2029 draft.

The second-order cost: no offer sheets

There is a quieter consequence that gets overlooked. Offer sheets must be compensated with the offering club's own draft picks — not picks acquired from elsewhere. Toronto does not have its own 2027 first. It does not have its own 2028 first. The Colorado pick, however useful in a trade, is legally useless as offer-sheet compensation.

That closes off the single most efficient roster-building tool available to a capped-out team with a thin prospect pool. We ran through the mechanics in August when the subject came up around a potential offer sheet Toronto was never able to make. The answer has not changed and cannot change until the summer of 2029.

What Chayka can actually do

The honest inventory: one incoming conditional first, a handful of extra second- and third-round picks accumulated through the Carlo and Woll trades, a prospect pool ranked in the middle of the league outside McKenna, and a cap sheet that needs LTIR to be legal on opening night. That is the toolkit.

The practical implication is that Toronto is a seller of futures only in an emergency, and a buyer only in the bargain bin. If this team is in a playoff race in February, the deadline move will be a depth defenceman or a bottom-six forward paid for with a second and a prospect. It will not be a top-six winger, because the Leafs cannot outbid a team that still owns its own firsts.

The counterargument — and it is a fair one — is that a team that just drafted first overall and has McKenna, Easton Cowan and Knies under 24 should not be spending futures anyway. Correct. But there is a difference between choosing not to spend and not having anything to spend, and Toronto is in the second category by inheritance.

What's next

Two things to watch. First, Colorado's start. Every point the Avalanche pick up pushes Toronto's incoming first later in the round and lowers its trade value; a Colorado collapse pushes the pick into 2028 entirely. Second, whether Chayka treats the Colorado pick as untouchable. A general manager in year one of a retool who trades his only first-round selection for a rental has made a decision about the timeline, and it would be a loud one.

You can track the full picture of Toronto's selections and obligations on our draft page, and the cap sheet that constrains all of it on the contracts page. The short version: the Leafs won the lottery and are still, in draft-capital terms, running on fumes until 2029.