"Whataboutism" is intellectually bankrupt. If something is a legitimate callout of hypocrisy, it doesn't matter who it's from, or how hypocritical the speaker is. It's the message, not the messenger, otherwise it's just the reverse of argument by authority. Ideas should be evaluated for their content.
> If something is a legitimate callout of hypocrisy
I'd like to nail down when accusing someone of hypocrisy is legitimate. (I don't think I'm disagreeing with your larger point, more clarifying.)
If the person is insisting that their arguments come from an innate moral authority, sure, pointing out that they can't live up to their own standards casts doubt on that moral authority or the feasibility of those standards. And sometimes people don't realize they're arguing from innate moral authority, so challenging them on that point can identify some unspoken assumptions. (All that said, it's clearer to plainly state, "I think you're implicitly claiming moral authority, and I dispute this," than to ask "what about X.")
Cook doesn't seem to be doing that, though. For example, "Cook told the new Stanford graduates that digital surveillance threatened innovation and would have 'stopped Silicon Valley before it got started.'” This is an argument that the process is innately self-defeating, which doesn't rest on his personal moral authority.
In this case, since he's not fundamentally basing his argument on moral authority, saying "what about" is simply an ad hominem tu quoque.
If the person is insisting that their arguments come from an innate moral authority
That part of their argument can simply be ignored.
Cook doesn't seem to be doing that, though.
I never said he was. I was specifically responding to the notion of "whataboutism" itself. That notion itself is philosophically bankrupt. Ideas should be judged on their merits, not on who has advanced them.
simply an ad hominem tu quoque
Ad hominem is another example of ignoring the message and nonsensically diverting attention to the messenger.
> Ad hominem is another example of ignoring the message and nonsensically diverting attention to the messenger
I see how it ignores the message but disagree that it's nonsensical.
I agree with you in that whataboutism calls into questions the intentions of the messenger: You are accusing them of trying to derail the discussion instead of addressing their point at face value.
However, I think your analysis is practically bankrupt and overly idealistic since it fails to address how saying 'what about this' can be an effective tool to wave attention away, or try to discredit another argument or 'message' as you call them.
This is like saying every request made in a DDOS attack should be taken at face value. We should never question the broader intentions of the request