re: NIL Tax Questions - Accountants Input Appreciated

The athletes will likely be independent contractors. They will receive 1099s. Therefore, they are on their own to remit estimated taxes and file a Schedule C at the end of the year. Unless they get help from a CPA or the university, they will be very surprised at year end when they have to pay up.
Just think of the ones who get free cars, then get 1099’d for the value of the car. But, didn’t cut the deal to get enough cash to pay the taxes.
I think some where down the line the IRS is going to stick it’s nose into all this and conclude the money paid by businesses (which are deducting the payments) are in excess of the fair value of the services the athlete rendered. Accordingly, the deduction taken in excess of the FMV will be denied. And then the dominos start to fall and the payments start declining.