It's called a grantor retained annuity trust (GRAT) and more than beng able to retain the initial investment at the end of a period of time, he would be able to take loans against the principal itself in the meantime (LALs).

However -

> The USPOC currently supports ~4500 athletes, or ~$22,222 each.

Machinations of the uber rich and the morality of them aside, they would've gotten nothing and now they're getting something.

But if he retains the money while its growing wouldn't that result in capital gains?

You can't claim a donation while still holding onto the money?

He'll donate to a trust/non-profit he controls that will direct the investment. That allows him to take the tax benefit today and keep the money

Not if he controls the funds. Tax deductions are only afforded to contributions if they are charitable and am actual gift. If the contributor benefits, it is bit deductible, and control of donated funds is a benefit, as is the ability to direct funds to a particular person or persons.

Billionaires can financial engineer their way around those types of rules quite easily

But once its in a non-profit you can't just take it back out for personal use can you?

No not directly but he can control it. So he can invest in a shell company that invests in other shell companies that buys shares of operating companies.

It’s not like he needs these funds to buy groceries or pay the mortgage. He’s essentially hoarding assets like all billionaires are.

This is a simplistic example for illustration, the actual financial engineering would certainly create much more complexity in order to obscure things for auditors and the like. But the point is that he/his fiduciary is the one controlling it all.