I can’t see them getting 10 to 12 1st rounders, but maybe 6. They would acquire a few top prospects, but without their own first rounders for 2 years, it doesn’t really help. Unless one of the trades are with Philly, to get their 1st back, it’ll be a retool, probably fairly deep, but the stupidity of Treliving sabotaged a true rebuild. You still have to ice a competitive team going forward.
Nope. If the Leafs play their cards right, they could get anywhere between ten and twelve 1st round picks worth of value and that’s on the low end because there are other ways for the Leafs to accumulate more 1st round picks that Chayka has done before.
For the purpose of this discussion, when I say “1st round pick” it is a means of value. That means it could be a former 1st round pick, a current 1st round pick, a top prospect considered as valuable as a 1st round or a young roster player who was a 1st round pick or equal and significant value. For example, Rantanen cost: Logan Stankoven (young roster player equivalent to a 1st round pick in value), conditional round 1 pick in the 2026 draft, round 3 pick in the 2026 draft, round 3 pick in the 2027 draft and conditional round 1 pick in the 2028 draft. That is considered the same value as three 1st round picks and two 3rd round picks.
Step 1: Decide the goal is to do a full rebuild. The Leafs don’t own their own 1st round pick for 2027 or 2028. That makes tanking good for Boston and Philadelphia. However, if they use the 2027 regular season as a year to rebuild the value of players, they can start the fire sale at the deadline. And yes, one of the deals could be to get the 1st round pick back from Boston or Philadelphia but that depends on the situation those teams are in at the deadline.
Step 2: Trade Matthews. He’s the biggest chip. If Matthews goes around January, absolutely everybody else jumps ship willingly by the deadline.
Step 3: Retain salary on big contracts to increase return. Matthews is incredibly valuable as is. But if he scores 40-50 next year and is 50% retained, that’s extremely valuable to a contender. And if one contender is in on Matthews, multiple others will join the bidding war. The same would happen for Nylander 50% retained. And OEL. And Carlo. And Tanev. And McCabe. Teams always overpay for depth D at the deadline. The Leafs have four pieces, one of which the Leafs themselves pissed away a 1st and a top prospect to acquire last year.
Matthews 50% retained (6.625 AAV until 2028) at the TDL or 2027 draft: Four 1st round picks. Matthews, the 50 goal scorer, is already worth four 1st round picks. At 6.625, he’s worth more. With an extension, he’s worth even more. Four 1st round picks is the LOWEST POSSIBLE PRICE for that type of value. As many as five or even six pieces could be demanded if a bidding war begins.
Nylander 50% retained (5.75 AAV until 2030) at the TDL or 2027 draft: Three 1st round picks. 40 goal, 80 point player for 5.75 is EASILY worth three 1st round picks, maybe more.
Tanev 50% retained (2.25 AAV until 2030) at the TDL: 1st round pick. Players like Tanev go for a 1st every year. Holding 50% of salary reduces cap hit in case of injury and increases return.
OEL at the TDL: 1st round pick + prospect (High value player, low salary)
McCabe at the TDL: 1st round pick (Leafs paid a 1st for McCabe)
Carlo at the TDL: 1st round pick (Leafs paid a 1st + Minten)
Tavares at the TDL: 1st round pick (If Laughton cost a 1st, Tavares would get one easily as a 30 goal, 70 point player and low cap hit)
The Leafs, needing to rebuild, won’t need the cap space until beyond 2030 when all those contracts expire and while all the new prospects are on cheap ELC. Leafs could also continue to take on bad contracts for draft picks as Chayka has done many, many times before to reach the cap floor and increase draft capital. If the Leafs take 3 or 4 bad contracts, that could also add up to more 1st / 2nd round picks as we saw the Leafs pay many times to dump the likes of Marleau and Mrazek.
That’s twelve (minimum) 1st round picks for a full tear down fire sale and doesn’t even include 1st round picks the Leafs could bring in for bad contracts.