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Gilgamesh would probably finding Kiritsugu entertaining in the same way he does Saber if he were to find out his wish for the Grail, but what with the way Kiritsugu treats Servants as complete tools and has no respect for heroic spirits, I don't see their partnership lasting long enough for that to happen. And Gil certainly wouldn't be up for serving as a decoy by parading around with Irisviel.
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