Typically in organizations this large, trouble makers are "promoted out" so as to minimize the damage they can do to the organization while minimizing the risk of any legal blow back from an outright firing. I think the author here understands what is happening to him and seems to be describing these events with a sense of melancholy or sadness about being removed from a project or product that he cared deeply about.

I read much more of a cheeky tone, mixed with perhaps a dash of melancholy. I think the tone here is more one of jaded skepticism that his new role is more important than his old one. And he's probably right, from a certain point of view. But that probably means he should have declined the promotion.

He admits that he was probably on the chopping block for quite a while at the end. And yet, he calls the essay "Firing Frankness"? Comes off as bitter, to be totally frank.

I agree. The author is clearly detached and saddened by events; any perceived "tone-deafness" probably has more to due with the individual reader's jealousy or envy of his station than with the overall story he's telling.

What is there to be envious about?

Maybe I was just totally missing his tone. I'll give it another read and use this voice. :) thanks.

It helps if you've read the rest of his series on his history in technology and at Apple, where he adds more context. But it also helps if you have management/political experience.

Essentially, he was being "promoted" from the top of the engineering organization to the bottom of the CEO's political organization. This meant that in practice he had much less control over his own future and was now mostly accountable for his perception amongst his fellow political peers, who (as other people have already discussed here) were already "Yes Men" for the CEO and not interested or even able to consider contrary positions.

>> Just for crossing the street, I’m rewarded with an even fancier President (of Apple Products) title

This could be humble bragging - I got a promotion, but I'm not gonna toot my own horn. It could also be a poke at the C-suites to gain support from the masses (they don't deserve what they get just because of where they sit) or out of resentment. It could also be a psychological defense attempting to frame it as though he didn't belong there in the first place, rather than being fired for screwing up. I'm sure there are plenty of other interpretations, but I can't think of a really positive reason for making such a statement.

He's not speaking to a crowd of people that are currently struggling with day-to-day necessities, he's talking to people that work in tech and some of whom work at very high levels, so it isn't really tone deaf.

I hear what you are saying with the audience, I was overselling my point. But I do work in tech and I still find this really un-relatable. I've never even come close to the place where receiving a raise or a promotion is unappreciated.