There's a current tax dodge where high net worth people get pledged asset loans and spend that, because loan proceeds aren't taxable, but selling stock is. Selling stock in a company you're the CEO of also can be bad PR, but pledging it might be less bad.

OTOH, selling stock to redeem a pledge could be scrutinized for insider trading, and such a large amount could move the stock, so if I were loaning the money, I would require some large multiple of the loan in pledges -- enough so that I would expect not to have to call the pledge, because I know it will be a disaster if I do.