cville deac
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How does a landowner lose money in Virginia prior to 1863?
In Jefferson's case, you start with having expensive tastes, especially when it comes to french wine and books. Add in building a really expensive house on top of a small mountain, and then rebuilding it a couple of times when you get bored with it. Then have slaves who are good craftsmen build you a bunch of nice furniture to go in your really nice house but not really use their labor to make and sell other furniture to try to make a buck. Then have a farming operation that usually lost money. Jefferson had artist's mentality and didn't have a practical bone in his body. And yeah, he probably lost more $$ for someone who employed slave labor than most anyone in history.
Don't know Madison situation as well.