I was listening to this week’s Upgrade and the topic of Tim Cook’s gifting of a trophy to Donald Trump came up. The short version is that both Myke and Jason believe that Cook didn’t personally enjoy this, they both think he “debased” himself by doing it, and that he really didn’t have a choice because the real problem here is that the US government is corrupt and this is the sort of thing they make companies do.

I appreciate this position, and I 100% agree that the primary problem here is the Trump administration itself. It is absurd that the supposed only way for Tim Cook to run Apple right now is “debasing” himself and kissing the emperor’s ring. This is how things work in Russia, they are not how it’s supposed to happen here.

However, I don’t like the presumption that Tim Cook and Apple are just passengers here in our descent into fascism. I also don’t like the suggestion some make (not exactly Myke and Jason, to be clear) that Apple is a soulless corporation who doesn’t care about the things that they believe are important or are willing to sacrifice profit margins in support of those goals in some cases. Obviously some of that is useful marketing as it makes the company look better, but these aren’t evil robots running the company, they’re real people who I believe on the whole want to make the world better.

If Apple committed to doing more American manufacturing so as to avoid the tariffs, I think that would have been fine. Doing so in a joint press conference with Trump would get a sad head shake from me, but not ire. What bothers me is celebrating Trump by publicly presenting him with a trophy that signals to the world that you really, really support this guy. I appreciate that Cook isn’t someone who spends much time sharing his opinions on political and social issues in public, but let’s be clear, whenever he has shared an opinion this year, it’s 100% been in support of whatever Trump wants. In fact, it’s been more public adoration than basically anyone else in the massive tech companies besides Elon Musk (and even Musk has expressed disagreements with Trump) have given him.

To Cook’s credit, Apple continues its diversity initiatives and climate goals, both of which operate directly in opposition to what Trump wants for the US. But let's say Trump notices those and farts out a post on Truth Social saying Apple must stop these programs; my money's on them being gone in a week. We can't upset the mad king.

Maybe Cook actually does hate all of this, and he's willing to take the reputational hit to protect his company and the people who work there. I'm not talking shareholders, I'm talking the employees working there who might have to get laid off if the government targeted Apple and financially hurt them. Maybe in his mind he's just doing what needs to be done, even if he personally greatly dislikes Trump. I actually think there's a decent chance this could be the case. What I'll say, though, is that if you prop up and celebrate and "thank you sir, can I have another?" with the bad guys long enough, you're not a good guy "playing the game" to get by, you're just on the bad guys' team now.

Mr. Cook, I've respected you for many years and I adore the products your company makes. Being the CEO of Apple must be one of the hardest, most complicated jobs in the world, it's not something I could ever do myself, and I appreciate that in 2025 you are put in impossible positions on many fronts. 9 years ago one of your VPs said it took "courage" to push phone technology forward by removing the headphone jack from iPhones. We are in trying times as a country and the stakes are higher than they were for that headphone jack; if you have any more of that courage stored up, we'd love to see it.

You don't need to smack him down or anything, but something, anything to indicate that you're not actually 100% in the bag for this guy would be good to see. Until then, it just looks like you're legitimizing and celebrating a man who's stripping people's rights and actively using the military to take over cities managed by his political opponents.