Robert Bruce died in 1329. According to Jean le Bel, when Bruce was dying he asked that Sir James, as his friend and lieutenant, should carry his heart to the Holy Land and present it at the Holy Sepulchre in Jerusalem as a mark of penance. John Barbour, alternatively, has Bruce ask that his heart should simply be carried in battle against "God's foes" as a token of his unfulfilled ambition to go on crusade. Given that Jerusalem had been in Muslim hands since 1187, this second is perhaps more likely. When Bruce was dead, his heart was cut from his body and placed in a silver and enamelled casket which Sir James placed around his neck. Early in 1330, Douglas set sail from Berwick upon Tweed, accompanied by seven other knights with twenty six esquires and gentlemen.