A pissed off judge can do more than just send someone to jail. They can claw back any illegitimate transfers and give them to someone else, like pissed off creditors. That’s what would happen to any Twitter assets in the event of bankruptcy, even if they technically no longer belonged to Twitter.
Bankruptcy isn’t just something you declare, like in an episode of The Office. It means opening up all your books to the courts and to your creditors. It’s like an IRS audit, except instead of a bored IRS agent you will face multiple openly hostile lawyers.
And if Elon actually didn’t care about losing $20 billion, then why go through the trouble of all these dangerous shenanigans? All the “Elon is masterminding the death of Twitter” simultaneously assume that he doesn’t care about losing his investment and he is desperately trying to cash in assets that belongs to other investors.