James Robertson writes about potential futures for ObjectStudio Smalltalk.
One option that might be in Microsoft's best interest could be Microsoft throwing a bit of money and expertise toward Cincom to get a Smalltalk running on the CLR. Work with the IronPython and CLR folks on dynamic languages, maybe even on some of the features Jim lists that make Smalltalk as good as it is.
Who knows? Could help Microsoft's dynamic language capabilities in general, and both organizations may benefit from a first-class Smalltalk system on that platform.