Oh man, the mention of ScriptSharp brought back memories. I started my career at MSFT on SharePoint and the front end was an ungodly mix of ScriptSharp and other stuff.
I vividly remember being in a meeting with the Exchange team (about building shared frontend components) arguing for us to adopt TS instead as it had a better experience and very rapidly growing popularity (that was about 10 years ago). Plus, as strong as Nikhil [0] was, he was basically the only person behind ScriptSharp while TS had a whole team.
Of course, this being MSFT, this effort went no where. While true that the TS toolchain lacked the tree-shaking that ScriptSharp had, I was just annoyed that we had to build stuff using what was obviously an dead-ish language with limited support, many flaws, and no resources to improve it.
But hey, at least it wasn’t GWT.
From what I've read, many of TypeScript's design regrets have political origins. Enums and other features that oppose TS's structural type system were added as compromises with C# developers in MS and similar negotiations with the Angular team in order to increase adoption of TypeScript over alternatives