To be deductible as a business expense, the payment must be ordnary, necessary, and reasonable (Section 162(a)). The ordinary criterion basically means that the expense must not be capital in nature. Because the expense relates to the future, it might not be an ordinary expense. Some capital expenditures are subject to depreciation or amortization. Other capital expenditures are not deductible until the owner sells the business. There may be some case law about whether such an expense meets these criteria.
Even if it is not a deductible expense, it is likely taxable to her. Gross income includes all income unless the nature of the income is specifically excluded from gross income (Section 61(a)). As to lawsuit settlements, only payments for physical injuries or sicknesses are excluded from gross income (Section 104).
Possibly, the payment is a gift. In that case, Tiger would have to file a gift tax return and pay gift tax. A gift is a transfer without adequate consideration in money or money’s worth. I do not think it is a gift because he is paying her for her silence, which is something he perceived to have monetary value.
Again, thanks..