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On TV last night there was a tax lawyer explaining how in New York where Weinstein lives, the IRS doesn't allow settlement payments to be deducted when filing taxes.
According to the lawyer that may have happened and can be an even bigger issue for Harvey Weinstein and his brother. I'm not sure why the brother was mentioned but both names were mentioned in this case.
On google there can be articles found regarding settlement payments and how one settlement can be deducted and a different one not.
On top of that the lawyer was clear that it also comes down which area/State and he was clear that under the tax law Weinstein can't deduct these payments.