Paul Jennings was born a slave on the Montpelier plantation of James Madison. He was sometimes a playmate for Madison’s stepson, Payne Todd. Madison’s wife, Dolly, had been widowed with a small child. Eventually, Paul became the body servant to James Madison himself. He accompanied the family to the White House when Madison became president. It is said that as the British army approached the White House in the War of 1812 to burn it, he helped Dolly save many White House treasures, including the portrait of George Washington.
Jennings returned to Montpelier to assist the president in his retirement and was present as the former president took his last breath. Jennings also took care of Dolly in her widowhood. While she had hoped to free him, Dolly was destitute and had to sell Jennings. Daniel Webster purchased him and set him free.
As a free man, Jennings found noble employment in Washington, D.C., assisted African-Americans coming north and wrote a book about his experiences. Jennings helped Dolly Madison in her destitute old age out of his own pocket. Why was Dolly destitute? It was because of Jennings’s old playmate, Dolly’s son, Payne Todd. Todd had lived in privilege but never found a real job, served jail time for assaults, amassed huge gambling debts, drank to excess, mismanaged the family business, lost the ancestral home and stole from his mother. It is an example that some have limited opportunities and make the most of them while others have great opportunities and squander them.
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