In retrospect, I wonder if his 1994 endorsement of Cuomo and his bizarre brand of "conservative" politics in NYC was part of a plan to run for governor of New York down the road -- as a DEMOCRAT.
Speculation runs rampant!
Quite frankly, he could have run for governor on the Nazi ticket in NY State and probably been elected in a landslide (/sarcasm).
The issue of Giuliani is not so much party affiliation and stands on issues, I think, as much as it is that's he's a man who tells you what he thinks, and what he's going to do, and then goes out and does it.