Maj. Gen. Nathanael Greene knew that the only threat to the upcoming South Carolina Legislature meeting in Jacksonborough was the British on John’s Island. He decided to eliminate this threat with a surprise raid on John’s Island.
Lt. Col. John Laurens and Lt. Col. Henry Lee would lead the Patriot expedition against John’s Island and would be supported by the main army under Maj. Gen. Greene. Since the Patriots didn’t have any boats they could only approach the island by a narrow canal to the Stono River called the New Cut. The canal could only be crossed two times each month, shortly after midnight when "the depth of water was not more than waist high."
The British knew about the strategic value of the New Cut and they placed a galley and two gunboats, four hundred yards apart, to guard the cut. The galleys had to remain apart so they could still stay afloat at low tide, and this left a gap that the Patriots could pass through. The tide gave them only small window to get in, strike the British, and get out.
Lt. Col. Lee and Lt. Col. Laurens decided to strike at John’s Island on December 29th, but they learned that the British had stationed troops on James Island across the inlet from John’s Island. To go ahead would be too risky and the operation was canceled until a later time. Two weeks later both commanders agreed to make another attempt.
On the cold and rainy night of January 12th Lt. Col. Lee and Lt. Col. Laurens rendezvoused at a point less than a mile from the New Cut. Maj. Gen. Greene and the main army had broken camp the day before and marched towards John’s Island in case the British tried to send reinforcements to assist Lt. Col. Craig.
As Lt. Col. Laurens waited, he addressed his men, appealing to their honor and their patriotism. He issued instructions to his men on how to cross the waist deep water without getting their arms or ammunition wet. He told them that no one was "to fire or advance without orders, confusion only can arise from unconnected individual efforts."
Lt. Col. Laurens then divided his force into two columns. Lt. Col. Lee commanded one and Maj. James Hamilton of the Pennsylvania Line commanded the other. At one o’clock in the morning the crossing began. Lt. Col. Lee sent Capt. John Rudolph across first with the Legion Infantry. As they moved they could hear the British sentries in the boats call out "All’s safe." Lt. Col. Lee’s column easily made the crossing onto John’s Island.
The second column under Maj. Hamilton soon broke contact in the darkness and disappeared. Lt. Col. Laurens searched for an hour and finally found Maj. Hamilton. Maj. Hamilton’s guide had deserted him leaving his troops to find their way on their own. That hour they were lost had seemed like an eternity. When the tide came in Lt. Col. Laurens had no choice but to call off the operation and recall Lt. Col. Lee’s troops who had made it on the island. On the march back across the New Cut, Lt. Col. Lee’s men found themselves waist deep in "mud, weeds and water." Several soldiers became stuck in the mud and "were obliged to be pulled out."
On January 14th, Gen. Greene had his men search the riverbank for a boat to ferry Lt. Col. Laurens’ troops back across the inlet to try again. To cover their withdrawal he brought up his cannon to fire on the galleys as they crossed. The artillery fired on the British vessels throughout the day, but the boats refused to withdraw. That night Lt. Col. Craig evacuated the island and the British galleys withdrew from the New Cut.
On the 15th, Lt. Col. Laurens and a small force of cavalry and infantry crossed the New Cut in a boat and found the remains of the British camp. It had been hurriedly abandoned. Lt. Col. Laurens captured a few stragglers, but Gen. Leslie had learned of Maj. Gen. Greene’s raid and had moved all his men to James Island. Lt. Col. Laurens did find a schooner that the British had loaded all their supplies onto.
He ordered his men to attack the schooner and his men fired a volley at her. This "threw the Crew into great confusion" almost making the schooner run aground. The British crew on the schooner stacked the baggage and used it as protection against the musket balls. They returned fire as their ship moved slowly away. Lt. Col. Laurens had remarked, "If I had a three pounder…perhaps She might still be taken."
Lt. Col. Craig’s new position was at Perroneau’s on James Island. Maj. Gen. Greene remarked, "We have got the territory but we missed the great objective of the enterprise." He withdrew to an encampment at Skirving’s Plantation, six miles in front of Jacksonborough on the road to Charlestown. The expedition was considered a failure, but it did eliminate the British threat to Jacksonborough.