The Butterworth Squadron was a British commercial fleet of three vessels, the Butterworth, the Jackal and the Prince Lee Boo, that sailed for the Pacific Ocean from London via Cape Horn in late-1791. The Butterworth was a whaling ship with a typical crew of forty-eight men. She is said to have originally been a French frigate of 30 guns, captured by the British. The Jackal (sometimes spelled “Jackall” or “Jack Hall”) was a small sloop that served as a tender to Butterworth. The Prince Lee Boo was a small sloop; by several accounts somewhat lesser than the Jackal. The vessel was named for Prince Lee Boo, a young Palau Islander who traveled to London in 1784.

The Butterworth squadron first wintered at the Hawaiian Islands in February 1793, when control of the Islands was divided between Kamehameha who controlled Hawai’i and much of Maui, and Kahekili who controlled the islands west of Maui including Oahu and Kauai. Brown traded in weapons with both Kamehameha and Kahekili, but strongly favored the latter. In particular, he entered into a contract with Kahekili giving Brown the title to the island of O‘ahu together with four islands to windward in return for weapons and military assistance suppressing a revolt on Kauai. It was during this time that the Butterworth squadron became the first European vessels to enter the inner Honolulu Harbor.