Type IXC U-Boat U-166, 1942
U-166 sailed from Lorient, France on June
17, 1942. The war in Europe was nearly three years old, but the conflict had
barely touched the waters of the Gulf of Mexico and the Caribbean. Only six
months after its official entry into the war, the United States was still
learning how to handle the U-boat menace and, generally speaking, wasn't
doing a very good job. Many merchant ships continued sailing alone and
unescorted, and some coastal cities were still reluctant to enforce blackout
regulations -- after all, the blackout was bad for tourism!

U-166 with her commander,
Han-Günther Kuhlmann (bareheaded, top), before her patrol. Image courtesy
the PAST Foundation.
Kuhlmann's first war patrol as commander
started off inauspiciously, when he intercepted the 84-ton Dominican
schooner Carmen off that country's northern shore on July 11. Not
wanting to waste valuable torpedoes on such a small target, he attacked on
the surface and sank the boat with gunfire. Two days later bigger game
appeared, the 2,309-tom U.S. steam freighter Oneida, off the eastern
tip of Cuba. Kuhlmann sent her to the bottom with six dead and continued
west along the Cuban coast.
On the evening of July 16, 1942, about
thirty miles northeast of Havana, U-166 encountered an ancient and tiny
motorized fishing vessel called Gertrude. Kuhlmann may have been
amused that this little boat bore the same name as his wife. The 16-ton boat
was far too small for a torpedo, so he ordered the trawler's three-man crew
into a motorboat and sank the trawler with gunfire. The motorboat ran out of
fuel before reaching Cuba, and the crew drifted for three days before being
picked up in the Florida Keys.
Kuhlmann and his crew never knew about
it, but their encounter with Gertrude gained some notoriety after the
trawler's crew was picked up and questioned by the U.S. Navy. Press
releases, always looking for a good propaganda angle, suggested that
Gertrude had been attacked and "hijacked" for food "by a Nazi U-boat
crew apparently desperate for provisions." The resulting article appeared in
the New York Times on July 28 and undoubtedly caused a few chuckles,
especially when readers learned that the trawler's cargo consisted of twenty
tons of onions.
For the next two weeks, Kuhlmann
patrolled off the Cuban coast and gradually moved northward into the
northern Gulf of Mexico. By the end of the month, U-166 was off the mouth of
the Mississippi River, in an excellent position both to intercept traffic
coming in and out of New Orleans and also to encounter tankers steaming
eastward from the Texas Gulf ports. Oberleutnant Kuhlmann was
probably getting anxious for a suitable target; he hadn't come five thousand
miles to sinking fishing boats. But patience paid off. On the afternoon of
July 30, Kuhlmann's lookouts spotted smoke away to the southeast. It was the
passenger steamer Robert E. Lee. Neither the steamer nor the
submarine would survive the coming encounter.
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