Night Battle near Lunga Point
On 4 September Gregory, in company with Little, were returning to their anchorage at Tulagi after transferring a Marine Raider Battalion to Savo Island. The ships decided to remain on patrol rather than risk threading their way through the dangerous channel at night. As they steamed between Guadalcanal and Savo Island, three Japanese destroyers entered the Slot undetected to bombard American shore positions. Early on the morning of 5 September, Gregory and Little saw dashes of gunfire believed to be from a Japanese submarine until radar showed four targets, apparently a cruiser had joined the three DD's. While the two outgunned but gallant ships were debating whether to close for action, a Navy pilot who had also observed gunfire believed coming from a Japanese submarine, dropped flares almost on top of the two APD's. Gregory and Little, silhouetted against the blackness, were spotted immediately by the Japanese destroyers, who quickly opened fire. Gregory brought all her guns to bear but was desperately overmatched and less than 3 minutes after the fatal flares had been dropped was dead in the water and beginning to sink. Two boilers had burst and her decks were a mass of flames. Gregory’s skipper gave the order to abandon ship, and her crew reluctantly took to the water. With all of Gregory's and most of Little's crew in the water, the Japanese ships closed the area of what remained of both US ships and began shooting at the helpless crews in the water. All but 11 of Gregory's crew survived, 6 of them swimming through the night all the way to Guadalcanal. Gregory sank stern first some 40 minutes after the firing had begun, and was followed 2 hours later by Little.