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The Oath of X cycle triggers on each player's upkeep and targets an opponent that meets certain conditions. Who controls this ability? The controller of the enchantment or the player whose turn it is?

For a concrete example, suppose I have Oath of Scholars and Rayne, Academy Chancellor on the battlefield. At the beginning of my opponent's upkeep, Oath triggers and they choose me. Do I get to draw from Rayne?

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The controller of a permanent always controls that permanent's triggered abilities. This is covered in rule 603.3a:

A triggered ability is controlled by the player who controlled its source at the time it triggered, unless it’s a delayed triggered ability.

The source, in this case, is the Oath of Scholars enchantment itself. This ability is not a delayed triggered ability, so you don't have to account for that.

So, Rayne's ability will not trigger if you are chosen as the target for your own Oath of Scholars.

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