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The so-called black hole shadow is not a silhouette of a black hole but an image of a collapsing object or a white hole. Hence it is nontrivial whether black hole shadows merge with each other when black holes coalesce with each other. In this paper, by analyzing the null geodesic generators of the event horizon in Kastor-Traschen spacetime which describes a coalescence of black boles, we see that observers who will never see a merger of black hole shadows exist.
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Okabayashi et al. (2020) studied this question.
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