TBF ... most of Virginia's presidents were clustered (4 of the 1st 5) during a time when there were a lot fewer states and Virginia was one of the 3 or 4 most populous. Wilson was the most recent, and he wasn't living here when he was elected.
It's a common trope that Wilson was the first President from the South since... Zachary Taylor, as he was born and raised in Virginia. I believe he was born in the middle of the Civil War, if I'm not mistaken. That said, his academic and political career took place elsewhere. He still still very much a son of the South, however.
Wasn't one of his Cabinet members, Josephus Daniels IIRC, a leader of the Red Shirts? Pretty sure Claude Kitchin, an ally of Wilson's on everything besides the war/preparedness against Germany, was also a leader of the Red Shirts.
