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actions speak louder than words and all that strikes me as a hollow shell of a person

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None of the above feels like Cook to be honest. He’s had f-u money for decades by now. If anything he seems to be a very corporate, very loyal to Apple person. If he thinks the interest of Apple is best serve by appeasing Trump, he’ll put his personal qualms to the side and stick to his job.

The bet he’s making though is that there’s more hurt in defying the Trump administration than if playing nice with him for 4 years and try to leave it all behind once that page is turned. Maybe his forthcoming retirement is part of his view - him leaving in due time may help move Apple along.

He could be both an embarrassing coward, and a greedy monster. Either way he gets money and power. There's no 4 d chess in kissing Trump's ass, just venality, though I'm sure he's telling himself something different.

as I write in the piece there's simply NO NEED to be so enthusiastically supportive of Trump. In fact I'd argue it harms the brand. Apple has enough influence and lobbying Apple could get pretty much everything they want without Cook ever leaving home.

I don’t think that’s his ethos though. He’s the stalwart of Apple’s destiny so I think it’s just his (and the board’s) calculus that playing nice with Trump today is less risky than giving the administration the cold shoulder (and temporarily hurting the company’s reputation in the meantime).