The thing about stock trading that most media people forget about is the word ‘trade’ - that means there has to be a buyer wanting to purchase his shares. Without enough ready buyers, the price will continue to fall as supply outstrips demand.
DJT trade volume is currently less than 6M shares a day (he has over 114M shares so it will take many weeks to fully offload them), so the very second Donald signals even his intent to sell the price is going to tank to penny stock territory. This is always the problem when majority shareholders try to sell large positions…it signals to the market that insiders are trying to cash out and that results in panic selling by everyone else. All sellers and no buyers = price crash.
If he hangs on to his shares and loses the election (*fingers crossed), the company is ultimately doomed. Either way he’s still going to walk away with a lot of money but a multi-billion dollar payday is unlikely. Only way he really wins here is by also winning the election.
ETA: One thing that is more likely to happen is after the lockout period is over, Donald is free to pledge his shares as collateral on loans. That’s basically how Musk, Zuck, Bezos, et al leverage their large stock holdings to fund their lavish lifestyles.