Why would he buy out of pocket. If he can get the price back up to just $11, which is only break even for most LTSH, his combined RSUs and options will be worth $10 million. The silver lining is that his grants may motivate him to sell the company sooner rather than later, because if he kicks the can down the road the effect of dilution will lessen the value to shareholders. IMO he may be motivated to get the price up and lock in a sale for around $500 million/$10-$11 pps net of cash then he takes home $10 million. Given the value destruction we have seen, that would be a good outcome.
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