Oh, he could well win the nomination.
And then would get creamed in the general election. Kerry got killed in 2004 because of his baggage. Rudy has quite a bit of his own - personal issues and crony issues with Kerik. The Dems will use Kerik to absolutely savage Rudy's standing to carry out the WOT.
And that doesn't even get into the issue of a guy on the far left of the party trying to hold it together when HE endorsed a Dem in 1994. Party loyalty works best when you have practised such yourelf.
"Kerry got killed in 2004 because of his baggage." It wasn't mere "baggage" which killed Kerry but the fact that there was a band of men who were not going to allow his TREASON and gratuitous amplification of his "heroism" to go unchallenged. Kerry would have been elected but for the Swift Boaters.
Guiliani has NO such baggage. What are a bunch of Welfare Queens going to complain that he threw them off welfare?
Kerik is just an adulterer and NO ONE will care about him or that issue since the RATs worship one.
Intra-party squabbles in 1994 mean nothing particularly when the guy he was against will CAMPAIGN for him.
If such concerns are the best you can come up with get ready to see Rudy not only nominated but a big winner.