In simple terms, if the car comes to him as a gift and meets the criteria to be taxable, then the car will be taxed as normal; however, should he then pass the car on as a charitable gift, the taxable amount at the time he makes the charitable gift will be deducted from the taxable amount at the time he won the car.
Normally, gifts like this are taxed upon bestowal, so it will probably be that you get a tax refund for the amount deducted, as opposed to a straight cancelling out. This will generally be worked out at the end of the tax year and make up only one part of their overall tax calculations for the amount you should be refunded for that year or in certain cases, the amount you still owe.
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