I will judge him for two periods:
2011-2020 - Ive & Cook era
Things went by pure inertia until around 2015, when things starting going off. Between the Maps failure, the Apple car failure, the butterfly keyboard, the poor Macbook Air 2020 with a joke of a cooling system (a fan without any heatpipe going to it lmao), it was a terrible era.
People swear for Apple in this era due to the iPhone X, but aside from that, it was series of rehashes before (6-8), and afterwards as well (X-11,12-15). Outside of the iPhone, iPads were suffering, Macs as well. Airpods were the result of starting the trend of favoring shareholders over consumers. Homepod became the new trash can. The watch, well, it exists but did nothing special.
2020-2026 - Boiler plate is heating up
Decades after having a tight grip over their stuff, we finally see them being pushed into doing common sense decisions, like the adoption of USB-C on iPhones. Proper specs on their devices (iPhone 17), but I guess generosity doesnt last long.
The walled garden is finally starting to show cracks, after several decades of them neglecting due to 'security', and yet, taking 1 year to fix reported security issues. New CEO will take the ball, and I think, will probably suffer the heat of the last years of miss-decisions