Major “Bloody Bill” Cunningham

William "Bloody Bill" Cunningham (1756 –1787) was an American loyalist infamous for perpetrating a series of bloody massacres in South Carolina's backcountry in the fall of 1781 as commander of a Tory militia regiment in the Revolutionary War. Though his family were loyal to the British crown, Cunningham initially enlisted in the Continental Army as part of the State of South Carolina's 3rd regiment in 1775. His tenure in the rebel army was an unhappy one and Cunningham changed sides to fight for the British in 1778. He earned the nickname "Bloody Bill" for the violent, ruthless nature of his raids on rebels and patriot civilians.

The Cunningham family emigrated from Scotland late in the 17th century, settling in Augusta County, Virginia. William was born in Virginia in 1756. When William was 10, the Cunningham family migrated to Ninety-Six, South Carolina along the Saluda River in 1766, an area known for its fierce Whig-Tory rivalry that occasionally spilled into violence. William is represented as a lively, honest man with a quick temper. He was an expert horseman, for which he gained popularity among his peers. When the revolution began, the Cunninghams quickly became one of the most powerful Tory families of the South Carolina backcountry. William's cousins Robert and Patrick Cunningham were prominent planters who became high-ranking officers in loyalist militias. Despite his family's allegiance to the British, William joined the Patriot cause in 1775 for reasons that remain unclear.

William Cunningham enlisted in South Carolina's 3rd Regiment of Rangers on the Continental line under Captain John Caldwell and Colonel William Thompson in June 1775. Cunningham would later claim that upon enlistment he was promised promotion to first lieutenant and the right to resign if the company moved to the low country. On July 12, Cunningham's company took Fort Charlotte, seizing over 1000 pounds of gunpowder, 18 cannons, 15 muskets and 343 cannonballs. The seizure of the fort signaled South Carolina's entry into the Revolutionary War and the beginning of hostilities in the backcountry.

Cunningham's regiment arrived in Ninety-Six on November 19 to support Major Andrew Williamson against a band of Loyalist militia. The battle lasted for three days before the sides agreed to both lay down their arms. Despite the truce, Colonel Richard Richardson dispatched a fleet of Rangers to surprise a Loyalist party the morning of December 22. In what became known as the Battle of Great Cane Break, the rebels captured 130 men while suffering no casualties. The loyalist group was led by Cunningham's cousin Patrick, who managed to escape into Cherokee country.

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