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I looked at the docs and I couldn't find an initiation date but what I'm talking about when this was first initiated, did he have any choice BUT to sell it??

He is not required to set up a trading plan, no. In fact, I believe he holds something like $600m of Apple stock (probably less after the past couple of days).

But once the plan is set up, then he has to follow it. The plans can be like "sell any shares I receive as compensation over the next 5 years", "sell 10k shares every three months", "sell 5k shares if if price hits $x" or even "buy $1m worth of shares if price hits $z". But once it's filed it's automatic. It is possible to change or cancel, but it resets a cooling off period and attracts unwanted attention, both from shareholders and the government.
 
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