Dukakis had this strange idea that he was JFK's Second Coming-a Massachusetts politician with a Texan running-mate launching a Democratic renaissance after eight years of Republican plague. Since Carter had crashed so spectacularly, and an 1964-style victory impossible, Kennedy seemed the model to follow. Democrats only wrote off the South after 2000, and early on Dukakis was actually competitive in border states.
When I look at the 1988 map, it's so bizarre to see WV Democratic but not Vermont, CT, MD, and DE.
West Virginia had an economic slump from 1979 that didn't end until 1994. Lots of Socially conservative democrats that went for Reagan in 1984 because Mondale was seen as too liberal. Dukakis choosing Bensten instead of a liberal northerner like mondale did with ferraro might of convinced them to come back along with people voting for dukakis out of protest over the economic slump in the state.
Also democrats were not as environmentalist as they were back in 1988. Environmentalism was largely just "make factories adopt stuff to stop pollution" not post-2000. When it became "shut down coal plants to reduce CO2". The heart of West Virginia industry is coal and democrats might of still won West Virginia post-1996 by never adopting carbon reduction policies but at the same time pissing off the environmentalist base.