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I don't know if he'll make it to the 6 month cliff, but he may be able to leverage the shares sooner without selling.
Nope. Unless the lockup is waived or modified by the board, Trump cannot "lend, offer, pledge, hypothecate, encumber, donate, assign, sell, contract to sell … or otherwise transfer or dispose of" his shares (this language is well-tested boilerplate for any lockup agreement). In case it's not clear, that covers using them to get a leveraged loan.
Far more likely is the board simply waives the lockup which frees him to do whatever he wants, in which case my bet is he just sells off some or all of his stake 'cuz who gives a shit if one of his cult members catches the falling knife.
I'm fine with his cult members catching falling knives, but I'd rather he be forced to take the L along with them. The can all hang out together in El Salvador.
The lender would have to be a moron to offer that loan.
That or the "lender" doesn't consider it so much as a 'loan' but rather as a 'payment'.
Thinking Saudis or Kuwait, or whoever wants to buy and own Trump.
Gotta remember, a presidential candidate is for sale right now. Not that he wasn't bought before.