Libertalia: Winds of Galecrest

If I gain 2 doubloons from the Freed Prisoner (20) and then gain 2 more because I copied the Freed Prisoner’s night ability with the Witch (15), do I discard the Freed Prisoner?

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No
If you ever gain 3 or more doubloons with the Freed Prisoner's night ability in a single night, discard the Freed Prisoner. If the Witch gains 2 doubloons using her ability, that’s the Witch’s doing, not the Freed Prisoner. However, using the Witch to gain 3 doubloons by copying the Freed Prisoner's ability will still cause the Prisoner to be discarded.