I'm pretty sure a team can trade away a pick that already has conditions on it, however, it needs to be made explicitly clear what the alternative is.
So, back to the Toronto example, Toronto could offer any other team the pick, but it needs to be made perfectly clear, "if the pick goes to Carolina, then Team X instead gets ___"
I believe
That seems to be the case, at least in some cases. I was wrong in my guesses there.
Now I wonder if the pick that is traded to two teams need to be to some extent protected in the first trade, and you can only trade in the second trade the part of the pick that was protected with a condition in the first trade, as you technically still retain the protected portion of the pick.
The Sharks 1st 2019 mentioned on the previous page would suggest this. After trading the lottery-protected pick in first trade to BUF, in the second trade to OTT they trade the same pick as playoffs-protected (which is the portion they still have themselves), which means that there will be no scenario where their trading partner won't get that particular pick 1st 2019 within their respective condition. (the conditional lottery-protected 1st 2020 to OTT in the second trade is for the case where SJS qualifies for playoffs and the 1st 2019 goes to BUF by the first trade, so that in every scenario OTT will get a 1st)
I *would guess* that "if we happen to not have this pick at that time, you'll get X instead" condition where you explicitly tie it to the currently-unknown outcome of another previous trade might not be accepted at the CR.
If this is the case, TOR could still trade the their 1st 2020 in a second trade as bottom-21 protected. That doesn't project to be a very valuable asset obviously, so finding a trading partner might be a challenge.
They *probably* can't trade the 1st 2021 in a second time, as that pick is officially unprotected and so currently encumbered for CAR in full... though, in practice TOR will retain their 1st 2021 if their 1st 2020 isn't top 10 (a very likely situation). So maybe 1st 2021 *could* be traded in a second trade as 2020 top 10 protected.
I guess it depends on if the CR goes by the book or by the practical outcome when accepting trades. As tradeability is a thing that the League cherishes, they well may lean on the latter.
We know from the Haula to CAR trade that CR goes through the conditions and the various scenarios that might arise from them and red-flags scenarios where the condition would cause a "failure" (in faulty computer program style). We also know from Haula trade that they *do* accept trades with complex utter madness conditions as long as they in practice can work out. If TOR can formulate such conditions to the trades that in no scenario a failure can happen (and which still are acceptable to their prospective trading partner), maybe they can conditionally trade their 2020 and 2021 1sts for second time.
Hilarity will ensue if the trading partners will further use these conditional picks as part of their own subsequent trades. They are a bit of high risk - high reward assets: a high-odds hero-or-zero flyer at a top 10OA in the speculative TOR 1st 2020 second trade case.
