Jesse Barrett "Oley" Oldendorf was an admiral in the United States Navy, famous for defeating a Japanese force in the Battle of Leyte Gulf during World War II. He also served as commander of the American naval forces during the early phase of the Battle of the Caribbean. In early 1942, a secret group of senior Navy officers empaneled by President Franklin D. Roosevelt assessed him as one of the 40 most competent of the 120 flag officers in the Navy.

The Battle of the Caribbean refers to a naval campaign waged during World War II that was part of the Battle of the Atlantic, from 1941 to 1945. German U-boats and Italian submarines attempted to disrupt the Allied supply of oil and other material. They sank shipping in the Caribbean Sea and the Gulf of Mexico and attacked coastal targets in the Antilles. Improved Allied anti-submarine warfare eventually drove the Axis submarines out of the Caribbean region.