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For its antonym, m-w windfall page lists affliction, bane, curse, evil, plague, scourge but i think all do not fit so well.

"windfall" means some good things came free in surprise, such as a fortune inherited by surprise from a remote relative...

"afflicction", "bane", etc.. seem mean "bad things" but not cover the "by surprise" part...

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The closest I can come is stroke of misfortune (for which stroke of luck is a second antonym, along with your query word windfall).

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There is no precise antonym for 'windfall', either in its original meaning of 'a fruit, especially an apple, that the wind has blown down from the tree' (OALD), or in its metaphorical meaning of 'an amount of money that sb/sth wins or receives unexpectedly'. (OALD). If things are not blown down by the wind, they are in their natural state. If things are not unexpected, they occur normally.

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  • What about disaster or catastrophe, like a tree that has blown down on a house? – benjimin Apr 1 at 13:43
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To develop the required polarity we could characterize 'windfall' as an event define by its context. For example, a windfall, for the serendipitous, could be a perfectly ripened fruit arriving at the point of one's most intense hunger; for the calamitous, it would be, perhaps, a large tree felled upon one's most valuable possession when one can least afford it.

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