Fun homework assignment for you. Who was the last deadline rental, who didn't come with an extension in place, that got multiple 1st round picks?

2019 matt duchene was 2 1st 1 was conditional does that count?

Not really. The condition was that he had to re-sign so he'd inherently no longer be a rental. This condition is also no longer allowed by the league. It's pretty much the example that proves the rule. No one is paying multiple high cost assets for someone that will only be there for the 1 run.

oh well the other 1st would be under the assumption that the leafs know they can sign him if not would be a 2nd or 3rd

See my note about this condition no longer being allowed by the league.

yes i know but what im trying to say is dubas trades the 1st if he really believes they can sign him. and if he doesnt think they can then they offer less no conditions

Leafs can't afford another expensive winger.

Couldn't you just sign and trade to avoid the conditions

They could do a sign-and-trade, but Toronto would want a trade-and-sign so that they can negotiate the terms of the contract with Tarasenko and they would rather pay less in assets. Would the Leafs be interested in a trade-and-sign? No, because Tarasenko is going to cost much more than 4m and they don't know what their cap outlook will be beyond next season, which means they might jeopardize their ability to sign Matthews or Nylander to extensions.

A last-round pick in 2024 is insufficient bribery for taking on a cap dump. Even if it's an expiring one.

I don't even want the Leafs to acquire Tarasenko. All I'm saying is that sign and trades simply avoid the whole predicament of no conditional picks for extensions

Yeah, I got you. I was just saying in this case it's unlikely since at least one side, if not both, would want to wait. So if the Leafs acquire him it's probably going to be under the assumption that he's a pure rental even if there is mutual interest in an extension. The solution would just be to remove a 1st to lower the return. Maybe the OP will do so in a future version.