This Baltimore lawyer-turned-soldier (whose name is pronounced with a long i sound as in sidewinder rattlesnake) oversaw the defense of Maryland against the British invasion in the summer of 1814. Many historians say it was Winder’s endless dithering that led to the United States capital being burned. He would have lost Baltimore, too, if it hadn’t been for the highly competent and determined Sam Smith.
Winder was a native of Somerset County on Maryland’s Eastern Shore. He moved to Baltimore in 1807, where he became a succesful lawyer and also an officer of the local militia.
Technically, Winder was a prisoner of war, but in the gentlemanly way that things were done in 1813 he was put on parole and was basically a free man. He spent the next year traveling between Montreal and Washington, successfully negotiating the end of a serious hostage crisis. It was during these negotiations that he met Madison and James Monroe, with whom he became lifelong friends.
Winder was released from “imprisonment” in July 1814 and the president soon appointed him to oversee the defense of Maryland. Although his credentials as a general were thin, Winder was related to Levin Winder, Maryland’s Federalist governor, a connection Madison thought would be useful in gaining support for the state’s defense.
Things didn’t go well from the start. Historian Harry Coles describes Winder as a “will-of-the-wisp commander” in his book on 1812: “From early July until he arrived at Bladensburg on Aug. 24, Winder was a study in unproductive motion.”
Theoretically, Winder commanded an army of a few regulars and as many as 15,000 militia. The reality was that of the 3,000 militia called up in July only 300 appeared for duty. Most of them didn’t even have proper weapons or ammunition.
To his credit, Winder tried to get more men and supplies but his pleas largely fell on deaf ears. Also, Secretary of War John Armstrong had not seen fit to give Winder any kind of staff or assistance despite his proximity to Washington City and his role in its defense, so Armstrong was forced to carry messages and run errands himself. He also did his own scouting to get the lay of the land. In a time when horseback was the swiftest mode of transportation over land, it was an exhausting task. The day before the battle of Bladensburg, Winder wore out three horses. That night he fell into a ditch in the dark and injured himself. The man had worn himself out to the point of exhaustion.
Winder did realize that Washington was vulnerable, but he argued that the capital was not a worthy military target. Commodore Barney told him that the British would be attacking, but Winder ignored him.
Winder’s untrained army of militia met the British at Bladensburg outside Washington. The American lines could not hold up under the pressure of British regulars and the defensive plan collapsed as the Americans retreated in what amounted to a route.
