During the early modern period (c.1500–c.1800), being an ambassador was no easy task. You were often sent to a country where you barely knew the customs, and you were also expected to rapidly learn the rules of that particular court, as well as finding ways in which to act as a real mediator between your homeland and your host country.
An Audience of a European Ambassador with the Grand Vizir
c.1740
Antonio Guardi (1699–1760) (and studio) 
Effectively, you were thrown to the wolves. Finding the right balance between reporting back to your masters – through finding secret information which would give them the upper hand in diplomatic negotiations – and appearing obedient and willing to preserve the treaties or alliance with your host masters, could prove to be very tricky indeed.
With this in mind, were ambassadors in fact spymasters?
Jean de Dinteville and Georges de Selve ('The Ambassadors')
1533
Hans Holbein the younger (c.1497–1543) 
In the 1530s, when Henry VIII was still negotiating his divorce from Catherine of Aragon with Pope Clement VII, Jean de Dinteville – the French ambassador to the English court – played an important role in reporting English affairs to François I, king of France.
François had promised Henry a few times that he would support his request to the Pope, and had instructed Jean to keep an eye on any further developments. Special envoys were also sent to the Tudor court to assist Jean de Dinteville.
As well as this, French ambassadors all over Europe kept up correspondence between them to ensure the preservation of France's interests. Mostly, this meant ensuring the union of François's second son, Henri, and the Pope's niece, Catherine de Medici.
It is not surprising, given the importance of Jean de Dinteville during his time at the Tudor court, that this portrait has become one of the most well-known Tudor paintings. It is an extraordinary work of art. It was painted by the famed Hans Holbein and, because of this, experts have spent a lot of time analysing it – and illustrating its symbolism to the public.
The painting is also interesting in that it presents Jean de Dinteville (on the left) as looking almost regal. Confident and comfortable having his portrait painted, Jean was clearly at the top of his game. While forging constructive relations during his audiences with Henry VIII and Thomas Cromwell, de Dinteville was François's ears and mouth at the English court, and this portrait emphasises his importance.
Other ambassadors have also been in the same tricky position as de Dinteville. Between 1563 and 1564, Sir Nicholas Throckmorton was caught between the wrath of two queens: Elizabeth I of England and Catherine de Medici.
By the summer of 1563, his constant involvement in conspiracies against the French crown had left the French royal family with no choice but to imprison him. His release took three to four months to organise, and during that time he continued sending secret dispatches to England to keep Elizabeth informed of the French situation.
In this portrait, Throckmorton's religious beliefs (Protestantism) are made quite clear – he was often reported as wearing this black apparel during audiences with the French monarchs. His dagger shows his courage and strength, but also his willingness to appear as such. The pamphlet or book in his right hand alludes to his spy skills – always being on top of what was published, both abroad and in England, either against or for Elizabeth.
There were two other English ambassadors who were definitely involved in spying activities.
Sir William Maitland of Lethington (1525/1530–1573)
George Jamesone (1589/1590–1644) (attributed to) 
Sir William Maitland of Lethington was both a Scottish ambassador to the English court and Mary Stuart's renowned secretary. He was involved in the conspiracy to assassinate David Rizzio, and he also attempted to bring about a union between the crowns of England and Scotland.
Sir Thomas Chaloner was an extremely experienced ambassador who served under four Tudor monarchs – Henry VIII, Edward VI, Mary I and Elizabeth I. During his lifetime, he was also sent to several different courts – those of Charles V (who was both Holy Roman Emperor and King of Spain), Henri II of France, the Holy Roman Emperor Ferdinand I and Philip II of Spain.
Naturally, the world of spies/ambassadors went far beyond the European courts.
Abd el-Ouahed ben Messaoud, whose portrait is quite well known, was principal secretary to the Moroccan emperor Ahmad al-Mansur.
'Abd al-Wāḥid bin Mas'ūd bin Muḥammad bin 'Anūrī, Moroccan Ambassador to Queen Elizabeth I
1600
British (English) School 
In 1600, he was sent to the English court to establish an official Anglo-Moroccan alliance, but prior to that, he paid close attention to the development of the Spanish Armada against England. He was even sent to England to discuss a potential invasion of Spain by Morocco and England. He was a spymaster against Spain and an astute ambassador to England.
It has been suggested that ben Messaoud and his portrait inspired Shakespeare's Othello character. Regardless of whether this is true or not (as it remains contested by some scholars), the portrait certainly illustrates ben Messaoud's influence and importance at court. His position as official Moroccan ambassador is clearly stated, and his sword compels awe and admiration.
Another non-European ambassador of note is Mirza Abolhassan Khan Ilchi, an Iranian statesman who was ambassador to both Russia and the United Kingdom.
Mirza Abu'l Hassan Khan (b.1776), Ambassador for the Shah of Persia
1809–1810
William Beechey (1753–1839) 
Ilchi is well known for leading delicate diplomatic negotiations when he was sent to George III's court in 1809 to discuss Russia's growing ambitions. In his diary, he revealed the complexities behind being an ambassador, as well as his personal views on the European courts and their modern achievements. He continued to serve as a special envoy for many years after.
Being an ambassador during the early modern period often involved being willing to get caught up in conspiracies. Ambassadors often developed a strong network of spies all over Europe, and even the world, in order to preserve their masters' interests – as well as their own.
Emmanuel Jakob Handmann (1718–1781) (attributed to) 
During the sixteenth and seventeenth centuries, it was often the same families who pushed their offspring forward for the roles of ambassadors or special envoys. As the world developed, ambassadorial skills developed too, but one particularly important skill remained a constant: being able to have their ears and eyes everywhere. After all, knowledge was – and still is – power.
Estelle Paranque, historian and author
Further reading
Nabil Matar, Europe Through Arab Eyes, 1578–1727, Columbia University Press, 2008
Catherine Fletcher, Diplomacy in Renaissance Rome: The Rise of the Resident Ambassador, Cambridge University Press, 2015
Tracey A. Sowerby and Jan Hennings (eds.), Practices of Diplomacy in the Early Modern World c.1410–1800, Routledge, 2017
