William Smallwood

William Smallwood was born in 1732 into a prominent Maryland planter family and received military experience during the French and Indian War before returning to civilian life as a planter and member of the Maryland colonial assembly. He developed an early reputation as a disciplinarian and organizer, qualities that made him a natural choice to raise and train troops when Maryland began mobilizing in the spring of 1776. The regiment he assembled — composed largely of Marylanders from the Chesapeake gentry and skilled tradesmen — was considered among the best-equipped and best-drilled units in the Continental Army at the time it marched north.

At the Battle of Long Island on August 27, 1776, Smallwood's regiment earned its place in the annals of the Revolution through an act of extraordinary sacrifice. When British and Hessian forces overwhelmed the American left flank and threatened to encircle Washington's entire army, Smallwood's Marylanders — roughly 400 men — were ordered to hold off the British advance at the Old Stone House near Gowanus Creek. They launched five successive charges against a vastly superior force, each attack buying precious time for the main army to withdraw toward Brooklyn Heights. By the end of the day approximately 256 of the Marylanders were killed, wounded, or captured. Washington, watching from a distance, reportedly remarked that he feared the day was lost. Smallwood himself was absent on court-martial duty that morning, and the regiment fought under the immediate command of Major Mordecai Gist. Smallwood went on to command the Maryland Line throughout the southern campaigns, fighting at White Plains, Germantown, and Camden, where his troops again suffered heavily.

Smallwood rose to the rank of Major General and served as governor of Maryland from 1785 to 1788, applying to peacetime governance the same methodical energy he had brought to wartime command. The sacrifice of his regiment at Long Island became one of the war's defining stories of disciplined courage in the face of catastrophic odds, and Maryland honored their memory as a founding act of the state's martial tradition. Smallwood died in 1792, leaving behind a legacy shaped as much by the men he led as by his own considerable service.