J.E.B. Stuart, Confederate cavalry commander, was known for cutting quite a figure in his dashing wardrobe, which included a red-lined gray cape and a plumed hat. So it should come as no surprise that a popular anecdote about Stuart revolves around one of his hats.
In early August 1862, following the Battle of Cedar Mountain, Stuart used the burial truce to meet up with three of his friends from the pre-war days who just happened to be Union officers. The battle had been a loss for the North, so when Stuart joked that the Northern newspapers would manage to report the battle as a Union victory, one of his friends, Samuel Crawford, was skeptical. So Stuart bet Crawford that if he (Stuart) was right, Crawford would owe him a new hat. And of course, the Northern press being what it was, it was only a few days before Stuart was delivered a new hat from Crawford.
A week or so later, Stuart was at Verdiersville, Virginia, preparing for a two-pronged attack on General Pope’s army. While waiting for news on the whereabouts of fellow Confederate General Fitzhugh Lee’s cavalry, Stuart took off his cloak and new hat and decided to take a nap on the porch of the hotel where he was quartered. He was awakened a while later by the sound of approaching horsemen. Stuart and his men figured that they were the long-awaited cavalry of Fitzhugh Lee, but it soon became apparent that they were actually Union soldiers who had made it through the Confederate lines. Stuart, leaving his hat and cloak behind, quickly leapt onto his horse, jumped the fence, and rode to safety in the woods.
The Union soldiers gathered up the things the Confederates had left behind in their escape, including Stuart’s hat. When Stuart reunited with his men, it was obvious that he was missing his trademark hat and they teased him about it. Stuart wrote his wife, “I intend to make the Yankees pay for that hat.”
Four days later, Stuart and his men began a journey to the rear of Pope’s army in hopes of cutting off the supply line. At Catlett’s Station, the Confederates found lots of Union supplies, but relatively few soldiers, so they attacked. The raid netted them all sorts of goods, from food to clothes to money to horses. They also found Pope’s dress uniform among some baggage, and it was given to Stuart, who wrote the following note to Pope: “General. You have my hat and plume. I have your best coat. I have the honor to propose a cartel for the fair exchange of the prisoners. Very Respectfully, J.E.B. Stuart.” When Stuart got no response, he sent the uniform on to the governor in Richmond, who displayed it in the state library for everyone to see.