i still stick to the belief that any MAGA benefactor could far simply give trump the money, and let him grift the gift taxes from other sources later on.
if its some foreign authoritarian BFF, they would need risk exposure to their valuable money laundering network, which is why putin may not be that interested. but koch,musk,saudis,etc... have more legitimate channels.

economic viability of TS cannot possibly be a factor in any rescue.
as you have rightly implied on recent DWAC history, legal shorts have both microscopic volume (few hundred shares, if any) with annualized cost of 250% the share price itself (+ theoretical infinite downside of meme spikes). so not a viable hedge against even a 0.1% long position.

but out of curiosity, you mean naked shorting as in the benefactor would be willing themselves to engage in criminal activity? or do you mean through some options play?

'Naked shorting is the illegal practice of selling short shares that have not yet been determined to exist or that the trader hasn't secured in some way.'
investopedia