Anyway, the fact that Luly started the rule 144 holding period for the ENTA stock on 1/4/14 means that he planned to hold his 243k shares for at least a year in order to be able to sell the shares on the open market without the company's having to file a special registration statement.
In addition, it is possible that the option was a nonqualified (non-incentive stock option, or non-ISO), given that it was for such a large block. The 'CEO exception' to the ISO rules prevents an ISO from being issued for more than $100,000 worth of shares to a given employee in a given year, measured as at the time of issuance. If the option was nonqualified, the holding period for the purpose of measuring capital gains did not start until the option was exercised and the shares actually owned. Therefore, he would have to hold the shares for a year or more in order to get short term capital gains treatment.
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