*Conditions: If Calgary sends the Islanders a 2019 2nd round pick, Flames receive the 4th round pick in 2019. If Calgary sends a 2020 2nd round pick, Flames receive the 4th round pick in 2020 instead.
Question: Is there a deadline for Calgary to declare, with this type of condition ?

Has already been decided that the pick swap is in 2019, because Calgary missed the playoffs in 2018.

I believe the deadline is the day before the draft lottery

It's already been decided.

I don't know if he was talking directly about those picks or a situation with conditions similar to those.

The 2019 draft