[Spooky23]

Because BillG missed the boat in the internet, and everyone knew that the web would crush fat client apps on the Microsoft platform. Java had a ton of traction and drained the Windows moat.

Microsoft’s strategy around identity, browser and Outlook was solid. Outlook cemented Office. AD made Windows Server a necessity. The dominance and stasis of Windows and management of Sun/Java litigation held webapps back for several key years.

That delay meant that Microsoft emerged from that era with .Net, SharePoint, Dynamics and the beginnings of what became O365.