Steve Ballmer was an underrated CEO

He's underrated in the sense that a lot of CEOs of his era completely destroyed their companies, see Intel, GE, GM, Yahoo, etc and he didn't. So that's already a win, he set up the company in a decent position so that when someone with more vision takes over they'll have something to work with, even if he didn't have the talent to pull things off himself. He had a couple of wins (Azure, Office 365) along with many many losses, and they're good enough to secure him a 6/10 on my ratings.

If you trust the article, then Azure and O365 are each, independently, easily Fortune 100 companies if separated. These "couple of wins along with many many losses" are some of the most valuable products in the world.

Imagine a VC fund that invested in a few dozen product companies, two of which were Azure and O365. Is that a 6/10 VC company? Why is the logic different for a CEO making bets for a company's next several decades?

Because the company has more strategic resources than a VC, and has need to defend existing businesses.

MS should've been able to simply just extend their OS monopoly into all platforms and all architectures, but they didn't, and to a vast swath of the world have become irrelevant, and worse, have lost their ability to become relevant.

It's a decline from being the monopolist to simply a player, sure they executed well in enterprise sales and was fast in picking up OpenAI, but they have lost the ability to use their strategic resources to save xbox, help azure overcome competition, or push a mixer or Surface or whatever.

Edit: For people who don't understand the last sentence think about the way that O365 was able to help MS push Teams to stave off Zoom and others despite being objectively trash. MS should've been able to keep control of the internet, but they lost their moat to Google (Chrome), and the same story for various consumer products. Bing was a decent win but with a better consumer story they should've also been able to threaten social and youtube and so on. But now they're completely irrelevant there.

> MS should've been able to simply just extend their OS monopoly into all platforms and all architectures, but they didn't, and to a vast swath of the world have become irrelevant, and worse, have lost their ability to become relevant.

Microsoft is, pretty famously, on the receiving end of one of the most significant antitrust judgments in modern history. Choosing to further a monopoly seems that it would be a phenomenally bad decision for the company.

Despite that, Windows remains the dominant operating system for businesses worldwide. So I would argue that the OS is far from "irrelevant".

Beyond the OS, they are comfortably #2 in the public cloud market, with little threat from #3. Indeed, #1 has been relatively stagnant in market share, while Azure has been steadily growing.[0] It seems that a consistently growing market share in such a large industry shows that not only are they relevant, but they are becoming more so, and have not "lost their ability to become relevant". Additionally, it seems that they are "overcoming competition".

> It's a decline from being the monopolist to simply a player ....

> MS should've been able to keep control of the internet, but they lost their moat to Google (Chrome),

They legally could not maintain that monopoly. Again, see the antitrust ruling. The antitrust case was about the impact on Netscape, and was too late to save Netscape. But it is a pretty straight line from a case about bundling IE with the OS.

To be clear, the finding in this case originally held that Microsoft needed to be broken up.[1] Microsoft won on appeal, because of impropriety by the original judge in the case, but the appeals court upheld all findings of fact.[2]

Much of what you are saying Microsoft should have been able to do on the basis of their OS monopoly would have been begging for further antitrust action.

> Bing was a decent win

Bing, on its own, would be the 12th largest tech company in the world, per the original article.

And Microsoft is worth $3T today, largely on the basis of investment under Ballmer (and continued strong execution under Satya). Is the argument that Microsoft should instead be a $10T or $100T market cap company today if you graded Ballmer better than a D?

[0] https://www.statista.com/statistics/967365/worldwide-cloud-i...

[1] https://en.wikipedia.org/wiki/United_States_v._Microsoft_Cor...

[2] https://en.wikipedia.org/wiki/United_States_v._Microsoft_Cor...