Thomas Jefferson
I bet it’s surprising to find America’s third president on this list, but he did make some boneheaded moves. Even though he was one of the principle authors of the Declaration of Independence, and was relatively popular in his time, he died poor and miserable, with creditors howling at the door.
You see, Jefferson loved expensive wines that could only be imported from France. He also had the habit of constantly renovating his home. Living his life with the mantra of “There’s no tomorrow,” he did things and spent money not worrying about the future and one day woke up to find he had no cash left.