I predict he'll win in a landslide because his opponent is a RINO joke and the state GOP is non-existant.
He will win by a landslide. Liberals will vote for him because he is a Democrat who worked with Clinton. Conservatives either will vote for hime or abstain because Weld/Cellucci/Swift line is simply unbearable. Trade Union and ethnic vote will go to him, because he seems to care about working class and families. College related people (there are many of them in Massachusetts) will vote for him because he is a professor. Reagan Democrats will vote for him because they will not be able to stomach Swift's running "mate".
In Massachusetts if you want a sensible person in the office you MUST look for a conservative or moderate Democrat like Silber. Do not look among the Tory Row Republicans.