Seems to me Tim Cook's legacy will be similar to Steve Ballmer at Microsoft. Great for shareholders, terrible for the company's long term competitiveness.
The iMac Pros are nice-ish machines, but I can't see Jobs trying to sell a >$10k BTO Mac as anything other than a very special edition with a whole marketing circus supporting it - not as a ludicrously expensive mainstream SKU with a "This is the price, you're going to buy it because it's a Mac, take it or leave it" attitude underlying the sales pitch.
Apple seem to be becoming increasingly tone deaf. The money may keep rolling in, but sooner or later there's going to be an event - a competitor, a new technology, a software disaster - that makes the wheels fall off.
Remember Next or the Lisa or the original Mac? Jobs was pretty good at trying to sell very expensive computers. The original Mac was priced equivalent to $5,877 in today's dollars. The Lisa was priced equivalent to $24,600 of today's dollars.. and we all know how expensive Next was.
Now they're selling $1,000 phones, gold watches, and machines that are way overpriced for what they offer. It's a noticeable shift.
This is no longer the case - the most expensive Apple Watch has a ceramic case.
I’m going to sell mine for $400 in two years, having cost me $25 a month in total For something i use a hundred times a day and take all my family photos with. I could have saved $10 a month by getting an iphone 8, big deal.
Tim Cook hasn’t incinerated shareholder funds. Most of the profits have been returned to shareholders as dividends, or saved overseas for them. His bad acquisitions have been relatively tiny, like Beats.
And as far as competitiveness goes, the Mac market share is at all time highs, iphone sales are st all time highs, and iPad still dominates the tablet market. Plus their app store and apple music dominate as well. Oh and Apple watch is the biggest selling watch by revenues in history, both now and it’s launch year.
Apple hasnt been wildly creative under Cook, but is still designing innovative new devices, Apple Watch, Airpods, the 5K iMac, HomePods, iMac Pro. Let’s just agree to ignore the touchbar macbooks;)
He’s not Steve Jobs, but has done better than i ever thought possible.
For pretty much everything that wasn’t consumer facing. Office 365, Exchange, Azure, CRM and SQL Server all saw huge growth under Ballmer. He really killed it in Enterprise, but as you mentioned, consumer facing products had several missteps (and where a lot more public).
Maybe Sundar Pichhai but he is young in his CEO role so it's too early to decide.
In tech: Google before Alphabet, the former Yahoo, the former Sun. Twitter did their musical chairs act, as well.