On 21 Jan, 1943, the Charles C. Pinckney (Master Frank Theoron Woolverton Jr.) straggled from the convoy UGS-4 in heavy weather. Early on the 27 January lookouts spotted a U-boat, the master changed the course, increased the ship´s speed and the armed guards fired at the U-boat (the ship was armed with one 4in, one 3in and eight 20mm guns).
At 20.43 hours on 27 January, U-514 fired three torpedoes at the Liberty ship, a lookout spotted one of the torpedoes 750 yards away approaching the ship off the port bow. The master tried to evade, but one torpedo struck just abaft the stem. The explosion ignited a portion of the cargo, the blast blew the bow off forward of the #1 hold and created a pillar of flame that shot skyward. The engines were immediately secured and the most of the nine officers, 32 crewmen, 27 armed guards and two US Army security officers abandoned ship in four lifeboats and one raft. A portion of the gun crew and the gunnery officer remained on board and opened fire at 23.08 hours, as U-514 surfaced 200 yards away. They claimed several hits and the sinking of the U-boat, but the Germans made an emergency dive and escaped undamaged. The crew reboarded the vessel, but the chief engineer discovered that he could not get steam up. At 23.26 hours, a coup de grâce missed, but a second fired at 00.11 hours on 28 January hit and all survivors abandoned ship a second time. The U-boat surfaced again, questioned the men in the lifeboats and then left her victim in sinking condition, which later sank over the bow.
The four lifeboats set sail, but during the night of 28 January, they became separated. On 8 February, the second mate, four men and nine armed guards in one boat were picked up by the Swiss steam merchant Caritas I and landed at Horta, Fayal Island, Azores. The other three boats with eight officers, 28 men, 18 armed guards and two passengers were never found.