At 19.30 hours on 30 Aug 1942 the unescorted West Lashaway (Master Benjamin Bogdan) was hit on the starboard side by two torpedoes from U-66 while steaming on a zigzag course at 7 knots about 375 miles east of Trinidad. The first torpedo was spotted by a lookout but the evasive turn to port came too late and it struck amidships forward of the fire room, followed by the second torpedo nearby. The explosions blew off the #3 hatch, destroyed the engine room and the bridge area and flooded the ship so rapidly that she rolled to starboard and sank within one minute. The ten officers, 28 crewmen, nine armed guards (the ship was armed with one 4in and two .30cal guns) and nine passengers (including two missionary families) jumped overboard and swam to rafts that floated free because they had no time to launch the lifeboats.

The 42 survivors on the four rafts remained together for three days until separated in heavy weather. On a raft with 19 survivors, an armed guard and the master died of exposure within three days and were buried at sea. The raft was spotted and supplied by an aircraft on 13 September, but the next day a destroyer (possibly USS Barney (DD 149)) passed the raft twice without locating them. On 18 September, the raft was sighted by three aircraft that escorted a small convoy of four ships and HMS Vimy (D 33) (LtCdr H.G.D. de Chair, RN) was sent to investigate it. The destroyer thought that it was a disguised U-boat and opened fire, fortunately missing with 16 rounds and immediately stopped fire after the sail was cut down. One officer, ten crewmen, one armed guard and five passengers (one woman and four children) were picked up by the escort, transferred to the Dutch steam merchant Prins William Van Oranje and landed at Barbados. Two men on another raft were located 25 days after the attack by a West Indian fisherman, but only one crewman was still alive when the raft was towed into Old Sandy Bay on St. Vincent. The other survivors on the remaining two rafts were never seen again.