The idea that a CEO will stand up to his democratically elected dictator is absurd. Why should he, when the dictator is merely implementing the policies he said he would during the campaign and still got elected? Why should he make himself and his company and his shareholders martyrs?
Because many people hold Apple to higher standards, that is why.
This is exactly what Apple did when they stood their ground against the FBI in the case of the San Bernardino shooter though. Of course, Obama could hardly be called a dictator, and wasn't a petty, vindictive man like our current president. But it'd still be good to see Cook rediscover that "fuck you, make me" attitude from the old Apple.