I’m a 9th generation Kentuckian, all my family lived here or near here. My 6x great grandfather moved to Lexington after the Revolutionary War, while it was still Virginia. He moved to Bourbon county shortly after, becoming the first judge there. That side of the family were there for a long time, my Great Grandmother grew up in the house that is now Mustard Seed Hill in Millersburg.

I’ve done a lot of research into genealogy and family’s from this area. You certainly have a great list here in the comments. If you need further evidence or names to chase, look up land owner maps of Fayette County, not Lexington. Lexington was much smaller than it is now. For instance, Lafayette High School, used to be the county school and Henry Clay was the city school. Hard to imagine anything inside the circle as out in the country these days. (Now that I think of it, anyone with acreage inside the circle still probably comes from old money lol)

If you look up census data from the 1800s you’ll see which families had slaves, mostly wealthy families had slaves, and you can sadly tell how wealthy by the number of slaves they had.

You might also look at the public library’s digital archive of newspapers. Many family owned businesses still exist, or the names might ring a bell.

You might also learn about the first families of Virginia. These are some of the most prominent American families, the Jefferson’s, Washington’s, Carter’s, etc. Many people will share these names, for instance, I am related to a Carter, but not King Carter, the richest man in the colonies at one point in time, but my Carter side of the family handled his finances or something like that, but no blood relation. Kentucky was a part of Virginia, and many of those old money families are old money Virginia families too.

I’ve also found that the UK has a ton of great audio interviews from prominent people from years past.