Actually Microsoft's earlier and very successful development tools were all dynamically typed versions of Basic.

Visual Basic, Access, Excel and ASP were all dynamically typed, and were very responsible for exploding Windows' market share from Windows 3.0 onwards as it encouraged many to start programming who never would have considered it before.

Unfortunately they created an ecosystem of novice developers that many within MS I think despised and looked down on and which gave their platform a bit of an unprofessional reputation.

Then along came Java and showed them that a relatively sophisticated and strongly typed language could raise the entry bar just a bit, but result in generally much higher quality of end product, so along came C# and out went VB and COM.

'Classic' ASP has also been responsible for much hair loss in early webmins.