[1][URL required, verification needed] Winder testified at the impeachment trial of Associate Supreme Court Justice Samuel Chase in 1804.

Exchanged the following year, Winder was appointed commander of the new 10th Military District, which composed the defenses of Washington and Baltimore, by fourth President James Madison on July 4, 1814.

In August, British Major-General Robert Ross with several thousand troops advanced from the Royal Navy ships anchored in the upper Patuxent River at Benedict, Maryland (in Prince George's County) upon Washington along with a simultaneous small naval expedition under Capt.

Winder made no attempt to skirmish or slow down the advancing British and decided on an all-or-nothing set piece defensive battle at Bladensburg.

As a result of the battle, the rough unfinished national capital fell easily into the hands of the British who marched in that evening looking for some authorities to surrender the town.

Winder would have participated in the possible battle at the extensive dug-in fortifications (planned and supervised by Smith in a fortunate premonition and foresight), on "Loudenschlager's Hill" and "Hampstead Hill" (now site of Patterson Park in East Baltimore), on the eastern heights, from the City, had the British decided to carry forward the attack and had the bombardment on Fort McHenry, on September 13–14, been successful.