Thomas Docwra was Grand Prior of the Order of St John at the time St John’s Gate was constructed in 1504. The Docwra coat of arms can be seen on the North and South sides of the Gate. He took over from Sir John Kendall in 1501 and served in the role until his death in 1527 when he was replaced by Sir William Weston, the last Grand Prior before the monastery was dissolved. Under his leadership, Hospitaller land in Hampton was leased to the Archbishop of York, Thomas Wolsey, who proceeded to build Hampton Court Palace on this site. The Hospitallers’ chapel bell can still be seen above the Astronomical clock at the palace.

The Prior of the Order was an important role within English society. Docwra acted as a public servant for Henry VII. In October 1507, he traveled to Picardy to treat for the marriage of Lady Mary, daughter of the King, to the Duke of Burgundy. When the Duke paid a return visit to England later that year, he was among the nobles that went to meet him at Dartford and later entertained the Bergundians at the Clerkenwell Priory in February 1508. Docwra would have interacted with Henry VII.  Based on Docwra’s claim to the common treasury that two falcons, purchased as gifts for the king, should be set against his accounts, it is thought that the pair went hawking  in 1506.  Furthermore, it is known that the King stayed at the Priory for a time in the Summer of 1508.

Painted by artist Edward Caruana Dingli there are several biographical clues in the portrait, a typical feature of Dingli’s work.  St John’s Gate, can be seen in the background of this painting, whilst Docwra’s coat of Arms and the flag of the order can be seen in the left-hand foreground.  It is unclear how accurate this depiction of Docwra is given that he died almost four-hundred years before the painting was made.

The Order of St John and the Maltese artist Dingli had a long-term partnership. He gave this painting as a gift in 1925, one of the first indications of a direct relationship between him and the Order of St John. He would receive a string of commissions in the following years including this painting of the Pilgrimage to Malta of 1926 and this painting of the Duke of Connaught. Dingli continued to make donations to support the work of the Order’s Museum in Clerkenwell.