We found out from Mike Veach with the Filson Historical Society this:
I looked at the images and I would say that these bottles are probably from the 1960s and were made by Schenley Distilleries. The Old Henry Clay label was owned by them at that time and came to them through the James E Pepper Distillery. I believe they also owned the Old Lewis Hunter brand as well. Old whiskey does not have much value because it is illegal to sell without a license. With that said, ebay does allow the **** of whiskey with a disclaimer that they are ******* the bottle, not the whiskey. This would be no defense if the tax collectors come for the seller, but it does give ebay a way to avoid prosecution. I would expect the Old Henry Clay would sell for less than $100 on ebay since it is a blended whiskey. The Old Lewis Hunter would probably go for about $100 as a straight bourbon.