I just don't see GT paying 3 contracts at once.
Not criticizing you, because I've seen this sentiment many places, but I really don't like this rationale for not taking action. The Hewitt buyout has absolutely nothing to do with today's GT basketball program. It's a debt that was incurred for the benefit of the program many years ago, and in fact is only still on the books because it was renegotiated at the time of his firing. And in fact it is treated as a debt on the GTAA's financial statements, so that the payments are not reflected as an operating expense.
It is a sunk cost, and should not affect current decisions. As a matter of fact, Gregory's buyout is also a sunk cost, because those are dollars that will be paid whether he is employed or not. The only relevant costs are the additional amounts that will have to be paid to a new coaching staff.
If the argument is that the GTAA's financial condition is too fragile to incur these additional costs, I get that. I understand the debt level is high, and GTAA is using an approach of relying on market returns on a portfolio to cover the debt service. I can understand a position that the GTAA needs to improve its cash flow before taking on additional expense, and that fundraising for "retire the buyouts" would be one way to do that. However, fundraising for "retire part of the McCamish debt" would be functionally equivalent, or fundraising for "endow the basketball team scholarships" could improve cash flow as well.
The statement "we can't pay for 3 coaches at one time" is really just saying "we'll be embarrassed because someone will make fun of us." If that's the problem, they just need to get over it.