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.
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.