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The subtilties of Southern politics are often lost on those who are outsiders. Even during the period of secession, the states of the Upper South were reluctant to leave the Union. Only after Lincoln determined to protect Fort Sumter did these states secede. Kentucky tried to declare neutrality; what became West Virginia represented a secession from Virginia after the Old Dominion left the Union.

In the era when the Democrats dominated the South, the Upper South and the Border States of KY, WV, and MO were never as strongly pro-Democrat as was the Deep South. Hoover defeated Al Smith in these states in 1928, and Eisenhower beat Adlai Stevenson in 1952 and 1956, even though the Democrats held most of the cotton growing states.

Add to this sociological changes to the South. MD is no longer a Border State, as the post-Civil War development of Baltimore as a major industrial center and the growth of the Washington suburbs essentially Yankeefied the state. VA and NC appear to be drifting in the same direction, with a large influx of "damyankees" (professional, postgraduate, lifestyle liberals) into the major metro areas. Of course, southeast FL has had strong ties with the New York metro area for decades, although the most recent generation of NY-NJ retirees has moved northward from Dade County into Broward and Palm Beach Counties.

Giuliani in 2008, a socially liberal secularist, may not play well in the socially conservative and mainly evangelical Protestant South and the Border States in the manner of Al Smith, a "wet" Catholic in the "dry" and mostly evangelical Protestant South.