In 1926, the Order commissioned a portrait of HRH The Duke of Connaught, Grand Prior of the Order of St John, to commemorate a new Royal Charter. This portrait was an instant success, receiving high praise in the press and featuring in the Royal Academy exhibition in 1927. The artist, Edward Caruana Dingli, hailed from Malta and enjoyed a longstanding professional relationship with the Order of St John. He painted an almost identical portrait of the Duke in the uniform of a Field Marshall which is owned by the National Army Museum.

Prince Arthur, Duke of Connaught and Strathearn, born in 1850, was the seventh child of Queen Victoria and Prince Albert. He spent forty years serving in the British Army, deployed around the Empire and served as Governor General of Canada between 1911 and 1916. He died in 1942 at the age of 91 and is buried in the Royal Burial Ground at Frogmore.

The Duke was Grand Prior of the Order of St John, and thus the head of the Order, between 1910 and 1939.  This video from the British Pathe shows the Duke inspecting nurses and ambulance men from the St John Ambulance Brigade in Hyde Park during the summer of 1931. As Grand Prior, part of his role was to attend parades and inspect members.