The War of Jenkins' Ear pitted Great Britain against the Spanish Empire between 1739 and 1748 over territories in the Caribbean, and it was in this context that English Admiral Edward Vernon took the decision to leave Guantanamo Bay with the intention of reaching Havana. But the plan failed after a siege lasting 4 months and the English ships were forced to return to Port Royal (Jamaica).
This medal was struck before the attempt had failed and commemorates a fictitious victory. On the obverse is a full-length image of Vernon with a sword in his right hand and his left hand on his hip. Behind him is a city, identified by the inscription under it as "HAVANA." On the other side is a ship in sail. The image is encircled by the inscription "ED:VERNON ESQ: VICE ALMIRAL OS [OF] THE BLUE [FLAG].'' It is encircled by a dotted line.
On the back is an image of the city of Portobello with English ships in the bay and an inscription that reads: "WHO TOOK . PORTO . BELLO . WITH . SIX . SHIPS . ONLY.'' On the exergue is the date NOV . 22 . 1739.
The image of the victory at Portobello was reproduced on the back of many of these medals.