A Conversation between Dolley and Aaron

Dolley Madison in One of Her Famous Hats

It was Aaron Burr who introduced James Madison to Dolley. Madison was a painfully shy bachelor. Burr was his friend from college. And Dolley was that flirty widow lady who lived in the same boarding house with Burr. Burr was not interested in Dolley, but he thought that she would do his friend Jemmy Madison a world of good. So he set them up. He told Jemmy that Dolley was interested in him. He told Dolley that Mr. Madison had shown an interest in her. That's all it took!

In Theodosia and the Pirates: The Battle Against Britain, I extrapolate from these well know facts about the first lady who loved hats to create a meeting between Aaron Burr and Dolley Madison right after the end of the War of 1812.

Excerpt from Theodosia and the Pirates

A milliners shop would have been just the place to find Dolley, Everyone knew of her fascination with head gear.

Excerpt from Theodosia and the Pirates

The letter from Jean Laffite to James Madison  did not meet with much better success than the letter from Theodosia to Dolley, pleading on behalf of her exiled father.

Excerpt from Theodosia and the Pirates

Aaron Burr may or may not have spoken to James Madison on behalf of Jean Laffite. But this small snippet of a conversation between Aaron and Dolley rings true. What else would they have said to each other?