Cooked
By all means, Tim Cook was a better choice for Apple CEO than most people you could pick out of a hat; perhaps even of high executives at Apple working at the time. But this judgement is not unalloyed.
The following things happened under his watch (in no particular order):
Apple decided against lowering the App Store 30% cut, despite internal arguments from top executives that the rationale was wearing thin (made just before his accession), got into a lawsuit with large app developers because of this inflexibility, held up a double standard of Apple's tracking not being tracking but app developers' tracking being tracking, and fought developers knives-out at every turn in general.
Apple maintained this App Store-only platform obsession even when it cost their users significant freedoms in authoritarian countries, and forced them into making hard-to-defend practical decisions, and unevenly applied policies.
Apple started focusing on services, and by all accounts aligning the incentives of the organization or its management on promoting them, to the point where setting up a new Apple device is a forest of money-milking, illegal dark patterns that are much more detrimental to the user experience than, say, stickers.
Apple developed a butterfly keyboard that was unfit for purpose, solved a problem no one was having, refused to fix it and held onto it for far too long.
Apple developed a function-row keyboard replacement (the Touch Bar) that was unfit for purpose, solved a problem no one was having, refused to fix it and held onto it for far too long. (At least the Touch Bar did not ship on every laptop they made.)
Apple left MacBook Air out to dry for years, refusing to produce a Retina display version until 5 years after first MacBook Pro had gained a Retina display, despite it being the most popular MacBook. (Apple was reportedly constrained by Intel chips of sufficient improvements to justify the cost of the speed bump, but this is nonsense. Adding a Retina display would have been enough to make it fly off the shelves, and it would have done right by the users who deserved them.)
Apple kept ProMotion/high refresh rate displays out of any non-Pro products until just last year, and they are still absent from most non-Pro products in the line-up. High refresh rate displays are no longer premium technology, and not offering them on everything is a bad look.
Apple committed to cancel Rosetta 2, a backwards compatibility layer that does not impede good ports, but does keep significant app libraries running, including some apps that may not be possible to update.
Apple introduced Mac Catalyst, the halfway house app framework for iPad apps to also run on Mac with very un-Mac-like behaviors, and largely abandoned it.
Apple introduced three new Mac Pro models, promising for two of them that they would be a spark of innovation and a testament to the importance of the creative community, significantly hiking the price of a computer of its type for all of them, before allowing them to languish un-updated beyond their initial configuration for years.
Apple maintained overpriced accessories for pro products, in the $999 Pro Stand for the Pro Display XDR and the $699 Mac Pro Wheels.
Apple maintained exorbitant prices for upgrades to flash storage and system memory, and consistently eschewed conventionally upgradable internal NVMe interfaces which would have provided comparable or better performance for lower prices (notwithstanding the 2019 Mac Pro, which could support an interface PCIe card for U.2 or M.2 drives).
Apple initiated and maintained dwindling attention to software quality and stability, leaving long-time system functionality to become less and less stable and more and more unpredictable over years.
Apple essentially replaced AppleScript and Automator with Shortcuts, which still does not even provide a debugging or stepping facility, and manages to be less scrutable even to experienced programmers than AppleScript is.
Apple savaged core functionality in Music (née iTunes) and Podcasts through rewrites that brought no improvements.
Apple, over a period of years, consistently degraded its user interface design language through purported motivations that hold no water and bring no value to users.
Apple removed useful connectivity that its users were dependent on (USB Type A ports on laptops, 3.5 mm headphone jacks on iPhones and iPads).
Apple announced an AirPower charging mat, that never materialized because they didn't know how to make it work, with the words "we know how to do this".
Apple began holding suppliers to higher standards, promising transparency, reports and steady improvement, but then silently cut off this focus.
In the middle of all this, Apple consistently shifted out actors, managers and executives that would be predisposed to take offense and want to fix these things out of the decision-making process and out of the lanes of success and power within the company. Some of these issues were eventually fixed after an uncomfortably long time; some were attempted to be fixed but relapsed. Instead...
Apple went from focusing on products to also focusing, an uncomfortable amount, on its own self-image and on how it alone is prepared and predisposed to successfully solve the problems they choose to attack.
I'm not saying all of these things are necessarily a personal ding against a CEO of a trillion dollar company. Some of these things, a cold-hearted, corporate, profit-maximizing CEO is not supposed, according to the archetype, to see as issues at all. But for a company that supposedly delivers customer bliss far beyond its competitors and holds itself to a high standard regardless of what their competitors do, just a few of these items should be cause for concern.
(And for a company so insistent on saying "no" to a thousand things to gain focus, you'd think they could at least have skipped introducing their own credit cards.)