You can't trade the Toronto 1st because it's conditional, it's either this years or next.

As for ending the rebuild, look at the position the team is in. The rebuild is over, this is just smart asset management

I was unaware that conditional picks couldn't be traded. What's your authority for that?

It's a league rule. It's very loosely worded, but by the letter of the law you can't trade conditional picks, just because you may find yourself in a situation where you might not have it, and the NHL doesn't want to allow the trading of ghost assets.

I think it may be loosely worded because there are two separate situations at stake here: (1) the pick is conditional upon events, such as a team reaching the third round of the playoffs or a player appearing in a certain number of games, and (2) the pick is conditional only upon whether or not it occurs in one year or another. I understand the need for prohibiting transfer of the first kind, but not the second. In the example given, Carolina is guaranteed to get a first-round pick in one year or the other; it's not a potentially disappearing asset.

I'm well aware, I'm just going by the letter of the law. In this situation it's a little like goalie interference. Can you tell me when it should be enforced and when not to? By definition it should always be enforced, I actually think we can trade the pick, but Toronto can't trade their 2021 1st for obvious reasons

See, I'm not so sure about that. I think that they could trade the 2021 1st conditionally, that if Carolina acquires it due to the conditions of the earlier trade, then the acquiring team for the later trade would get the 2020 first.

Here's the situation the league is trying to prevent: Minnesota trades Jared Spurgeon to the Ducks for Ondrej Kase and Anaheim's 2020 second, and the teams agree that if Spurgeon re-signs with the Ducks, then Minnesota gets Anaheim's 2021 second, too. That 2021 second is "frozen": trading it is barred for both Anaheim and Minnesota.

I don't see how that principle is expanded to cover a situation where a team owns a pick that simply has conditions as to year or elevation. With reference to Carolina specifically, I can't see why they would be prohibited from trading the Rangers' conditional third-rounder they acquired in the Adam Fox trade, but obviously the Rangers are precluded from trading their second (to which the third might elevate) because they might not own it.

my understanding was that we could trade the pick with the same conditions as what toronto sent to us. So if we traded the 2020 conditional first to vegas and the pick ended up being top 10, vegas would get torontos 2021 pick. However, im fairly certain toronto cant trade their 2021 first anymore until they know if the conditions were met or not.