Operation Boatswain (known in Hebrew as כ׳׳ג יורדי הסירה, kaf-gimel yordei ha-sira, "the twenty-three who went down with the ship") was the first of the operational missions carried out by the Palmach as part of the cooperation between the Jewish Yishuv in Mandatory Palestine and the British during World War II. The mission to sabotage oil refineries in Tripoli was unsuccessful, ending with the disappearance of 23 Palmach commandos and British SOE Officer Major Sir Anthony Palmer after their boat was lost at sea on May 18, 1941.
The Palmach was established by the Haganah High Command on 14 May 1941. Its two primary aims were to protect the Yishuv against attacks by Arabs in the event of a British retreat from Palestine and defence of Palestine against an Axis Powers invasion. Yitzhak Sadeh was named as Palmach commander. Initially the group consisted of around one hundred men.
In the early summer of 1941 the British military authorities agreed to joint operations against Vichy France forces in Lebanon and Syria. The first planned action was a sabotage mission against oil installations at Tripoli, Lebanon. It was feared that the refinery would provide the Wehrmacht aircraft fuel, and help thwart the planned invasion of Lebanon and Syria. The refinery was in an area well fortified by a unit of Senegalese troops from hostile French army.
A plan emerged for a motor launch, carrying 23 Palmach commandos and a Major Palmer acting as an observer, to embark from Haifa. Upon arrival, three of the Palmach would remain aboard while the rest sabotaged the Tripoli refineries. Practice runs in Caesarea had achieved excellent results.
On the night of May 18, 1941, the police were ordered to give up one of their best launches. Palmer and the 23 then took over the Sea Lion (Ari Hayam in Hebrew), cast off and were never seen again. It has never been determined exactly what happened to them.