Since then it's acquired a few new goodies, but most of what makes the extension great happened before Microsoft adopted it, so I shouldn't think there's anything stopping Ruby from doing the same.
Shooting from the hip, though, if the desire is for funding, I'm guessing Microsoft wouldn't see much strategic value in putting money into a Ruby extension. The Ruby ecosystem has largely congealed around an ASP.NET competitor, some devops tools that don't really work on Windows, and not much else. Python, on the other hand, is widely used in Microsoft shops. Windows shops need data scientists, too, and it's typically the primary language for cross-platform devops infrastructure.
There's also just a question of which way the winds are blowing. I know the TIOBE index needs to be taken with a dose of salt, but it is interesting to see that Python is entering the top 3 at the same time that Ruby is falling behind Object Pascal.