Dino is a personal role model of mine and I have actually patterned my own personal style after his. A cool aloofness & detatchment, and an exceedingly strong sense of privacy, and a good sense of humor about life's ups and downs (and oneself) has suited me very well. I credit Dino for that personal influence on my personality.
His politics aren't well known, I don't think. He did campaign for Jack Kennedy in 1960, but my understanding was that it was more out of loyalty to his pal Sinatra - who was much more of a Kennedy booster - rather than any strong personal political statement.
Dean was very old-world in many ways. The boozing was largely an act (though he was drinking and eating to excess late in life). It's said he knelt down before bed every day and said his prayers. He was an incredible family man - he had children with his first wife, and many children with his second wife, Jeannie, widely regarded as the true love of his life.
He had more than just a wandering eye - he loved women and had numerous flings and affairs. That's neither conservative nor liberal, I suppose.
He loved his children immensely - when his son was killed in a plane accident, Dino was never really the same and it started .
My gut tells me that he probably wasn't all that political. He probably had an old-world italian outlook on things - strong sense of family and especially loyalty, though not so much that would keep him from indulging in flings with attractive young women (he was even married to a woman in her young 20s late in his life, though it didn't last long). He probably had a live and let live attitude in a variety of things, but by the same token probably had great respect for society's traditions and conventions to a large extent.
The answer is 'I don't know what his politics were,' but my feeling is that he had what we would consider in 2004 a strong natural conservative instinct, but probably wouldn't be too overboard on any issue. I'd guess he would be a conservative leaning moderate who would probably not like flargant departures from tradition and western culture - same sex marriage, for instance.
Sinatra later in life was a Reagan man. Jerry Lewis, Dean's partner for many years, is pretty liberal, I think, as well as delusional. He recently 'confessed' to a torrid sexual affair with Marilyn Monroe, for example, which crosses well over into the delusional.
Just my gut. I don't think Dean would be a big conservative, though I am farily certain that given the focus and fixation of the highest profile liberal causes in 2004, he wouldn't be aligned very rightly with them at all, either.