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Let's say we had an Espeon with the Ability Synchronize that was holding a Toxic Orb and it became poisoned. Would Synchronize activate and poison the opponent?

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No.Synchronize will only pass on status effects to the opponent that caused them, it won't work if you have a flame orb or something like that.
Source: experience and bulbapedia.bulbagarden.net/wiki/Synchronize_(Ability)

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so if say, a Gardevoir were to use trick to switch from a flame orb while it's paralyzed, would it's ability burn the other pokemon as well, or amI just spouting nonsense?