Those two types are indeed equivalent by themselves. The problem comes when you want to store them somewhere nullable. `zero | one | two | zero` flattens back down to `zero | one | two`, you can't distinguish between the two zero/null cases.

On the other hand, `Option<Option<one | two>>` allows you to distinguish between None and Some(None).

This makes union types unsound in the presence of type parameters/generics.

TypeScript supports both anyway, because Hejlsberg cares more about being able to type existing JS antipatterns than about providing a sound type system.