Espionage Essay 2.1 Corrected

Trust in Untrustworthy
Businesses
Communication in diplomatic espionage from the early middle ages to the
16th century
Paper written in September 2009 by Desiree Scholten (3006913)
Trust in untrustworthy businesses
Table of Contents
Introduction: approaches to hidden communication 0
Early Middle Ages 3
14th and 15th century: origins of cipher and growth of diplomacy 7
The 16th century and further 15
Conclusion: Emergence of cipher, espionage and other misunderstandings 18
Bibliography 20
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Introduction: approaches to hidden communication
Where would 007 be without Q`s wondrous collection of explosive cell phones,
watches which are in fact satellite transmitters and navigation systems in lipstick? Nowhere-
he would be isolated from M and all other parts of the alphabet in London MI headquarters. In
the Middle Ages spies dabbled in politics and wagered their lives on infiltration missions, just
like James Bond...but without inventions with which he could make calls for help in case
emergency. How do these medieval spies complete their missions? How do they know of
their missions, and of the latest developments in politics, which may alter the approach with
which they undertake their missions?
In this paper I would like to investigate how written communication between spies and
those who sent them is conducted in an age where texting and e-mail were not an option. How
does one keep his, or her, messages secure from hostile eyes? I will sketch the development of
the uses of the written word, and in particular the word written in cipher as used in espionage
in the Middle Ages from the fall of the Roman Empire to the sixteenth century. As shall
become apparent in this paper, it is in this period that there is some form of repetition in
history: the use of written material in political practice and communication, as well as the
establishment of permanent communication services which function by means of ambassadors
and secretaries as it existed in the Roman Empire reappears in a somewhat altered form in the
Late Middle Ages. I do not mean to say that in the Early Middle Ages kings did not
communicate with one another or with their noblemen, but this communication was
conducted in a different manner; namely by means of people who were employed because of
their current situation and location, rather than the Late Medieval travellers who undertook a
specific journey at order of the king because of their function as official representative. It is
for this reason that communication and political change should not be studied separately.
One remark which inspired me for this point of view was made by Michael Jucker in
his article “Trust and mistrust in letters”: A need to hide what you have written lies at the start
of cipher when applied in diplomacy and politics.1 As I considered this idea I realized that two
things need to happen before this need to hide ones writing actually occurs. People will have
to start writing things when conducting politics, and people need to be certain that their cipher
1
Michael Jucker, “Trust and mistrust in letters: late medieval diplomacy and its communication practices” in:
Petra Schulte, Marco Mostert and Irene van Renswoude (ed.), Utrecht Studies in Medieval Literacy 13:
Strategies of Writing, Studies on Text and Trust in Medieval Europe (Turnhout 2008), p. 229
will hide the messages in a secure enough manner. It suggests a need for written
communication in politics, as well as a certain attitude towards cipher and written messages as
opposed to regular scripts and oral communication. To realize this is to further complicate the
study of this subject as apart from considering the issues concerning literacy and politics, the
mentalities towards these issues also need to be taken into account.
Before I undertake this odyssey I would like to briefly mention a few theories as
demonstration of the pitfalls of simplification of the process, as well as an explanation of the
need of my approach.
Jock Haswell`s account of the history of espionage is a clear example of the
complications which are involved in the study of espionage. He describes how around the
year 1000 spies were not perceived as different from scouts; they investigated how strong the
opposing forces were, what kind of soldiers they had, and the general morale and state of
health of the troops.2 Even after Genghis Khan had invaded the eastern part of Europe,
making use of informants to obtain insider information of the actions and thoughts of his
opponents, this kind of knowledge was not used in medieval warfare by commanders.3
Haswell holds it against the army leaders that they did not know the difference between battle
and warfare, in which warfare is a more comprehensive complex of tactics, strategy, and
information. But he judges the earlier Middle Ages in the light of Genghis Khan`s
organization, which is bound to deliver a distorted view. As I shall demonstrate in this paper
the early Middle Ages certainly did have a system of informants, and these informants were
capable of communicating with their king. That these informants did not work in the way
Genghis Khan did, is not to blame on the stupidity of early medieval warlords, but on the
needs of the time. Over time the jobs of spies didn`t really change; they have always searched
for secrets about alliances and military activity. The changes occurred in the political
background against which they perform their jobs. In the early Middle Ages the emphasis is
on internal politics. Kings try to assert and keep their rights on the throne over the other
nobles and their family. As internal politics settle down and kings gain stronger position
within the realm, they begin to look around and foreign warfare, as well as the battle for
support of dissident nobles, begins. This is also the period that diplomacy begins to grow, and
2
Jock Haswell, Spies and Spymasters, a concise history of intelligence (London, 1977), p. 23
3
Haswell, Spies and Spymasters,p. 25
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here David Kahn’s observation should be mentioned: as diplomacy grew in importance and
became an institution in the state`s organization, so too did espionage.4
I use the terms internal and external espionage here because of the lack of a better
terminology for this period in which the foreign office and its ministers do not exist, and in
which “foreign” and “home” are terms which can be stretched and which constantly change
due to military activity of individual lords. With the term internal politics I refer to any
political and military as well as diplomatic activity which takes place in the geographic and
theoretical realm over which a king can exercise authority. I specifically refer to the
theoretical realm, as in practice the power of the king is not absolute. Hence, if the king of
England sends spies to an area where the king of France rules I shall call this external
espionage. When nobles of England send spies to France this will be dubbed external
espionage as well. If these same nobles send their spies to English nobles, or the king spies on
his own aristocracy then this shall be called internal espionage.
In his book Espionage and Intelligence Ian Arthurson argues that the knowledge of
cryptography came into Europe by means of cipher books which Spanish and Italian
merchants brought home via their contacts in the Arabic world, where secret writing was a
long-standing practice. This also explains why Spain and Italy were ahead of the
developments in this field.5 I am not entirely convinced by this argument, as some forms of
secret writing already existed in a very simple form in games and magic formulae. It only
needed to be applied in another field of society and the development of the already existing
systems it into more complicated ones had to arise from its uses in political communication. It
is very well possible though, that the development of complicated cryptography systems was
spurred by new knowledge which came from the Arabic world. Another theory, which I
briefly mentioned before, is advocated by Kahn; namely that cryptology grew as diplomacy
grew: the maintenance of relations also called for secrecy in communication which was not
needed before.6 I do agree on this: the reason why cipher moved out of the realm of
amusement is that the need for this kind of hidden writing becomes a necessity. The
organization of diplomacy, and in particular the ways of communication in this area of
politics as well as the process of controlling war and peace by rulers, needs it.
4
Ian Arthurson, “Espionage and intelligence from the Wars of the Roses to the Reformation” in: Nottingham
Medieval Studies 35 (1991), p.142
5
Arthurson, “Espionage and intelligence”, p. 150
6
David Kahn, The Codebreakers, the story of secret writing ( New York, 1967), p.108
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Early Middle Ages

In the early Middle Ages cipher for concealing writing was used with an entirely
different focus than in the later Middle Ages. The methods used were quite simple: messages
were written vertically, as well as backwards, and more exotic elements were mixed with the
Latin script by means of Greek, Hebrew, Roman or Armenian alphabets.7 Besides the use of
existing letters, even if these were from a foreign script, messages were also encrypted by
means of the switching and adding of letters and made-up signs. From the 9th until the 11th
century only vowels were encrypted, in the sense that they were replaced by the consonant
that follows the vowel in the alphabet, a system inspired by that which emperor Augustus had
used. A variant on this is the replacement of the vowels by dots, crosses, or other signs. In the
11th century this repertoire was expanded by the replacement with roman numerals and
musical notes. The changing of both vowels and consonants with other letters and symbols
did not occur until the 11th century, and it had to wait for the 15th century before this was put
fully into use. 8 And even then, even though knowledge of multiple letters systems existed so
that each letter could be replaced by not just one but by multiple letters, mono-alphabetic
ciphers continued to be used,9 a sign that the more complex techniques were not deemed
essential.
Ancient Greek and Roman cryptography in a military context had existed; Kahn
describes a wide array of techniques throughout history ranging from the Spartan “skytale’10
to the checkerboard of Polybius11 and Caesar’s famous system of letter replacement.12 None
of this seemed to have continued in the early Middle Ages; it was used for subscriptions, had
magical connotations or was used as a form of amusement. There are but a few examples of
written material which had as their expressed purpose the hiding of its contents. Pope
Silvester II (999-1003), for example, hid his writings from curious eyes. He used the alphabet
which he as a monk had made on the basis of tironian notes to encrypt the concepts of his
letters.13 Besides this pope two rulers can be named: letters of Alfred I and Charlemagne to
7
Kahn, The Codebreakers , p. 150
8
Aloys Meister, die Anfänge der Modernen Diplomatischen Geheimschrift, Beiträge zur Geschichte der
Italienischen Kryptographie des XV. Jahrhunderts (Paderborn, 1902), p. 5-15. For more detailed study about the
techniques used in each Italian citystate in the 15th century, this is an excellent booklet, even though ist
assumtions seem a bit outdated concerning mr Meister`s search for a so-called “Urziffre“.
9
Arthurson, “Espionage and intelligence”, p.151
10
Kahn, The Codebreakers, p. 82
11
12
Kahn, The Codebreakers, p.84
13
Meister, die Anfänge der Modernen Diplomatischen Geheimschrift,p.5.
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their officers in cipher exist,14 but little study has been devoted to these, and the localization
of these letters has been impossible. It leaves me simply wondering why Alfred and
Charlemagne wrote in cipher, in an age in which few people could read anyway. Could they
not send word by messenger, as everyone else did? As a text is capable of acquiring meaning
apart from its contents, 15 in this context the concept of visual rhetoric is interesting. What
does it tell the nobles of the realm that their king uses a hidden kind of writing, one which was
primarily used for magical purposes? It might be far-fetched to assume that the use of secret
alphabets had any psychological value in warfare and communication at this time, as it is also
possible that it only seems like these two men were an exception in their use of cipher due to
the loss of like correspondence by others. But even then the question arises why there is no
other mention in the sources of cipher for political ends in the early Middle Ages. This
question has to remain unanswered for the time being, but there are indications that a
confidence in written material lacks so perhaps there are other motives involved which, at this
moment, are unfortunately left for speculation.
This lack trust which I mentioned earlier is expressed in a letter by Einhard, written
before 840, to his son: “[...] I think that it is better to trust a loyal man than a written
document, since if a document or a piece of parchment falls [out of the hands] of its bearer,
every secret it holds is revealed, but a loyal messenger, [even if] tortured, does not betray the
message entrusted to him.” 16 There is no mention of the possibility of encrypting a message,
although Einhard would possibly have used the counter-argument that codes can be broken,
and that he therefore prefers to entrust his messages to his servant. Walter Ong wrote:
memory dictates what is left of an oral message. Once forgotten, all traces are gone of that
which was once spoken and heard. 17 This disappearance of traces is of course very
convenient when messages are of such a nature that it would be better to pretend they had
never existed in the first place. Einhard is convinced that human memory is a much safer
place to entrust a message with sensitive information rather than the indiscreet parchment.
The recommendation of Einhard that his son send a messenger reveals that secrets were
present although not in written form. Indeed, as Paul Dutton writes in his article “Secrets in a
dark age”, scheming and conspiracies were everywhere at the Carolingian court, but these
14
André Langie, Cryptography: a study on secret writings, (London, 1922), p. 16 and Meister, die Anfänge der
Modernen Diplomatischen Geheimschrift, pp. 4-16.
15
Marco Mostert,“Literacy between power and trust: Why did the development of literacy accelerate in the 13th
century? ”, pp.16-17
16
Einhard to R., printed in: Edward Dutton, Charlemagne’s Courtier, the complete Einhard, p 158
17
Walter Ong, Orality and Literacy the technologizing of the Word as cited by Marco Mostert in Orality p 14
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secrets were whispers and signs, which would disappear with the body which made these
utterances and the receiver of the messages.18
The early Middle Ages are oral ages; sensitive information is sent by word of mouth
lest the parchment betray its secrets too easily. In Antiquity however, as I mentioned earlier, it
was more common to take precautions in the form of secret languages when sending written
messages. What is the cause of this change? The answer must be sought in the organization of
the state and its manner of communication in day-to-day life. In the Roman Empire
bureaucracy developed as the empire developed. The pair had grown up together, and the use
of written material in daily business was necessary. However, in the early Middle Ages the
new political structures which arose after the Roman Empire had broken apart could not use
this system. It was not theirs and had not grown into them as it had in the Empire. This meant
that written documents, which had played such an important role in day-to-day organization
of the Empire, was no longer all that important.19 And this is exactly the reason why cipher
disappears after its emergence in Antiquity. It is not because the Middle Ages are retarded and
dark, as Kahn suggests,20 but because there is a different structure in which the acquisition of
information (which, after all, espionage is all about) and the transfer of sensitive information
is different. In fact, certain situations show that gesture was more important than the
document itself. In 812 emperor Michael of Byzantium renewed the peace which his father
had made with emperor Charles the Great. The agreement was received in Aachen in the
church and was presented later once again in the presence of the pope in the basilica of St.
Peter.21 It is not the document itself that matters, but the fact that the agreement is eternalized
and handed over before the face of the Lord in Church. In the oral early Middle Ages secrecy
was not literary but it was bodily: Paul Dutton describes a situation in which legates
exchanged messages by means of signs and coded speech.22 Secrets were exchanged face-to-
face; hence the keeping of secrets a secret had little use for an extensive technology in hidden
writing. This was to change when in the later Middle Ages the growth of written culture in the
emerging bureaucracy evolved along with state structure in a process which is rather similar
to the intertwining growth of bureaucracy and the Roman Empire. I suggest that written
observations, the things spies see and hear and share with their masters, are a process which
18
Paul Dutton, “Keeping secrets in a dark age” In: David R. Knechtges and Eugene Vance (eds.) Rhetoric and
the discourses of power in court culture: China, Europe, and Japan, (Washington 2005), pp. 169- 198.
19
Marco Mostert, Oraliteit (Amsterdam, 1998), p. 18
20
21
Annales Regni Francorum in: King, P.D. Charlemagne: Translated Sources (Lancaster, 1987), year 812, p.
105-105
22
Dutton, “Keeping secrets in a dark age”, pp. 184-185.
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developed from the top down. That is not to say that this practice was enforced by law and
obligation, but already in 1260 Venetian ambassadors were obliged by law to write a report of
their missions as soon as they returned from abroad. Florence too asked her ambassadors to
hand in a written report, adding the requirement of having the document written in the
ambassador`s own hand.23 This is but one facet of the process, one in which writing down
experiences and thoughts becomes more and more common, and a sense of security is present
soon enough in the requirement of autographs.
The change of a mentality is more complicated than simple bureaucratic cooperation
and a change of trust; it has also to be deemed fitting to write things down. This changes in
the second half of the thirteenth century, when the sacral image of the written word
disappears,24 as described by Marco Mostert with regards to charters: in the second half of the
thirteenth century charters began to develop into products of evidence rather than declarations
of what had happened in the past comparable to the ways in which the Bible explained what
had happened in the past. In the realm of mentality, rather than the practicalities described
above, this is another factor which makes cipher emerge from the realm of magic and games
into practical day-to-day use: no longer was there a mist of mystery and sacrality around the
written word.
I am sure that if more study is conducted on the ways in which pragmatic literacy
gains prominence in daily life, we can begin to uncover the realm of secret writing put to
practical use. I argue that cipher in diplomacy did develop only in the 13th century because
from that moment on writing was integrated in society and could be used more and more for
such purposes as transmitting sensitive information. After trust in the written word in legal
documents had developed now this last bit of life could be put down in writing.
23
Donald E. Queller, The Office of Ambassador in the Middle Ages (New Jersey, 1967), p.141
24
Mostert, “Literacy between power and trust”, p.26.
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14th and 15th century: origins of cipher and growth of

diplomacy
Concerning the organization of espionage, several developments occur simultaneously
in the fourteenth century. One of these concerns the organization of geographic factors: to
have a place to go to when a spy has finished an operation, or when he is in need of
assistance, a place which is not too far away, is important. Cities formed bases outside the
homeland; in these cities or areas spies organized themselves, communicated with each other
and the homeland, and left for missions. Calais, an English city surrounded by French land
was a perfect place for the English.25 In 1385 Hennequin du Bos was captured in Scotland by
the English and sent to Calais with a box of letters. These letters contained instructions for
those spies who already were in Calais, awaiting instructions to be sent out from there, even
in various disguises.26 Places like Calais may not be available, in that case frontier zones were
also places where enemy and friend mingled, making it easy for spies to move about, just as
in places with little jurisdiction.27 It seems as if spies looked for places with as little
organization as possible when they were away from home, places where anything out of the
ordinary is not singled out immediately. Besides these external bases there were other
locations which were important for spies to exchange information: ports. Places such as
Dover and Wissant were perfect for spies who operated in France, because these cities
bordered hostile grounds, but were well protected and in the homeland.28 Even further inside
the homeland other channels of information were established to speed the transmission of
information. Edward IV organized a postal system on the islands to keep information moving
smoothly.29
Starting in the fourteenth century the sources do give more detail about individual
spies. It is at the start of this century that I can make an analysis of various groups of people
who seem to play a large role in espionage. All these men and women have an itinerant
profession in common, which allows them to easily bring information to and from large
distances. I do not imply that these groups only existed in the fourteenth century as spies were
active before that and information systems existed in the age of Charles the Great, but in the
fourteenth century the sources give more detail on the identity of these informers.
25
J. R. Alban and C.T. Allmand, “Spies and spying in the fourteenth century” in: C.T. Allmand (ed.) War,
Literature, and Politics in the Late Middle Ages (Liverpool, 1976), p. 84
26
Alban and Allmand, “Spies and spying in the fourteenth century”, p.84 and Allmand 40
27
Christopher Allmand, “Les espions au Moyen Age” in: L’Histoire 55 (1983), pp: 39-40
28
Alban and Allmand, “Spies and spying in the fourteenth century”, p. 85
29
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A first group I would like to mention are the merchants. Important for a spy is his
ability to move freely around. Merchants were a very handy and often used source of
information, but were also used to convey messages. In 809 king Godfred of the Danes is
getting slightly nervous about some rumours. Allegedly the mighty emperor Charles the Great
is angry with him over a campaign Godfred had led the previous year. To explain himself
Godfred asks merchants on their way to the king`s court to convey a message.30 As people
who travel far and wide, merchants are the perfect folk to ask to take a message over a long
distance. And when they are paid, and know themselves to be in a special position, they can
be even more convenient. In 1479 a Milanese envoy wrote from London that the merchants,
especially Florentines, were “benefited and enriched” by King Henry VII in return for
information.31 That they travelled around and told those they visited what they had seen
doesn`t make them any different from any traveller who can provide information of the
realms he or she passed through, but the fact that they were sometimes paid to obtain a
particular piece of information for a lord turns them into traders with a mission. Andrea Gritti
was one of these men who had trade as their first occupation, but did some jobs on the side. In
1496 Andrea Gritti was a Venetian advisor on trade relations in Turkey, but besides his work
as an advisor he spied on the Turks as well. In his letters he never dropped the appearance of a
mere merchant: the true meaning behind his correspondence with Venice was hidden under a
code: mercantile terms referred to political or military terms. Unfortunately a courier bearing
his letters was intercepted, and the danger to his personal safety grew so great that at one
point he requested Venice not to contact him for a while. It was not the end of his spy-career
though; later on he was able to make use of his status as advisor/ambassador to send letters to
Venice from prison. Of course these letters too contained other things besides the business he
was to relate on behalf of his office...32 Another man was the Italian Hughlin Grear from
Grassa in Bologna, who smuggled goods between 1377 and 1388 to England and at the same
time served as a spy for France.33 Where Andrea Gritti was a spy serving as an advisor,
ambassador and later on even became the Doge of Venice, Hughlin Grear lived an entirely
different life; he was a smuggler merchant who, through his shady contacts could come by
interesting information, rather than by keeping his eyes and ears open.
30
Annales Regni Francorum, year 809, p. 101
31
As quoted by Betty Behrens, “The office of the English resident ambassador: its evolution as illustrated by the
career of sir Thomas Spinelly, 1509-22” in: Transactions of the Royal Historical Society fourth series, volume
XVI (1933), p. 165
32
James C. Davis, “Shipping and spying in the early career of a Venetian Doge, 1496-1502” in: Studi Veneziani
16 (1974), pp. 101-104
33
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A second group of strangers whose presence is not perceived as strange by locals are
clerics. These men too, despite their avowedly sacred ways of life, were eyed with suspicion
by the authorities. In England alien priors were ordered by letter to keep any information they
might have with them, that is- don`t send anything to their homeland.34 It is remarkable that
the letter which mentions this restriction states that the transmission of information by letter
as well as by word of mouth is forbidden, this indicates that both were both used, one as
dangerous as the other. I will return to the duality of oral and written messages later. Cases
show that the authorities were not wrong in their suspicions: In 1416 Craquet, the abbot of the
Benedictine monastery of Fécamp, was sent to England both to establish a daughter house
there and to collect information.35 Another cleric who was in a similar position was the prior
of Hayling in Hampshire. He too was a French monk who corresponded with his homeland
while in England.36 Apart from letting monks settle in a monastery in England, the French had
other ways of getting their men in ecclesiastic positions, even for internal espionage. In 1384
Laurence Pussyn of Normandy had been using papal permission concerning his presence to
obtain a position in the Church of St. Peter Port in Guernesy for espionage purposes.37 Here,
as in all other cases, it becomes obvious that spies are no mercenaries who have nothing better
to do: they are men with good positions, even papal provision, and they are used as an extra
pair of eyes and ears in high positions.
A group apart from the strangers and natives are the scouts, as these are professionals
operating in hiding, but not living a life as secretly for example as spies at court. However,
this modern difference is not always made in the sources: in 1389 Philippe de Mézières wrote
in Le Songe du Vieil Pèlerin: “The use of spies is always necessary but especially so in time
of war, both to observe the enemy and to keep the commanders fully informed of their
intentions.”38 In practice men like Pierre, who was sent at the end of the Hundred Years War
by the English to De Fougères, a small village in France, received assignments which were to
explore the area ahead of an army, and possible routes for armies, fortified villages and other
problems the army could encounter. Pierre was to take a look at the defenses, as well as
particular techniques the French used so that plans for the campaign could be made.39 In 1429
the duke of Burgundy had sent Ivo Caret to London, to keep an eye on the duke of Gloucester
34
Alban and Allmand, “Spies and spying in the fourteenth century”, p.93
35
Allmand, “Les espions au Moyen Age”, p. 38
36
37
38
As quoted by Alban and Allmand, “Spies and spying in the fourteenth century”, p. 73
39
Allmand, “Les espions au Moyen Age”, p.37
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after he had heard some rumors that Gloucester was preparing an attack on Burgundy.40 In
this case Gloucester wanted to make sure he would not be surprised by an attack, but the
reports of spies could also be a reason to take action: The connétable of France, Arthur, was
besieging Meaux in 1439. His spies had informed him of the route the English army would
take to reach him. With this knowledge he could prevent such an attack. 41A similar example
is the march of Charles VII to Compiègne and Beauvais to re-establish his authority over the
region after spies had told him that a revolt against the English was at hands.42
The last group which should be discussed are the ambassadors. It is important in this
respect to remember that ambassadors were not always diplomats, since an embassy was
nothing more than formal privileged communication. Communication itself doesn`t change
over the Middle Ages; the way in which communication is conducted, especially formalized
communication, does. It is also important to remember that formal communication is not
always diplomacy, i.e. negotiations which are to result in a treaty if successful.43 This is
because ambassadors were in fact messengers who were sent on a mission with a temporary
and public character. The names for ambassador and the more common terms messenger and
nuncius were used without differentiating between the function and assignment of the
messenger, and the term ambassador itself does not arise until the 13th century in Italy.44
Embassies exist in two kinds, which can be combined: ordinary and circular embassies. The
ordinary ambassador travels to the court he is sent to on a mission, and returns. The circular
embassy stops at several places on the way with different purposes at each place.45 This does
not mean that the ordinary ambassador had only one letter with him; on his way he might
meet other lords who heard of his destination, and asked him to take their letters along. 46
Christopher Allmand summarizes the situation for ambassadors as spies very well with the
following words: “L’espion fassait en secret ce que l’ambassadeur essayait de faire au grand
jour.”47 Because these ambassadors do things in public, they cannot be spies themselves.
Their job is to collect, process, and distribute information to a certain location. The veracity of
their reports, and the honesty of their person is important, lest their reports will not be
believed by those who receive them, and their sources of information will shut down, or
40
41
42
43
Garett Mattingly, Renaissance Diplomacy (London, 1963), p. 26
44
Queller, The Office of Ambassador in the Middle Ages, pp. 60-61
45
Garett Mattingly, Renaissance Diplomacy (London, 1963), p. 34
46
Queller, The Office of Ambassador in the Middle Ages, p. 13
47
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rather, shut up. Confidence and a good reputation are crucial to the ambassador.48 Emanuele
de Iacopo is forced to write to his master that he cannot complete his mission: the King of
France has asked him to leave the city as he suspects that Iacopo has other, more nosy,
occupations besides negotiations.49 The importance of confidence makes the ambassador a
two-faced character: on one hand he is a dignified official, on the other he looks at his shady
assistants in the world of espionage for supplements to the official reports he receives.50 The
ambassadors are no men of too high a rank, so that they can easily converse with people of
lower ranks without arousing suspicion, and receive from these people complementary
rumours, as these men of low rank, such as servants, are not being watched as closely as the
officials. In 1453 Angelo Acciaioli, Milanese ambassador, writes in his letter how new
information “from some reliable informants” concerning the plans of the English influenced
the way he conducted his negotiations with the King of France.51 In 1460, Emmanuele de
Iacopo, received a secret visit from the Chancellor of Count Giacomo, who explained that in
reality he served the Duke of Milan as well, and that he had to tell him some interesting
news.52
The nuncii are used by ambassadors to send messages home. But the nuncii were not
always perfectly discrete or of unchallenged loyalty.53 As soon as ambassadors became a
standard function in international politics, sending messages in writing back and forth on a
regular basis, cipher becomes part of the regular array of tools a government has at its
disposal in communicating with and about foreign powers. The instructions of the Duke of
Milan to his ambassador Emanuele de Iacopo are clear: “[...] send as detailed information as
you can about every occurrence. Put the important matters in cipher; the others you can write
out in clear.”54 Michael Jucker warns us in this respect that written messages did not replace
oral ones, but rather gained a prominence over them, a situation of “plurimedia” and
“superimposition” of one over another arises.55 In this diversified situation one might suggest
that letters contained the less sensitive information, and orally transmitted messages contained
the most dangerous information, which was not meant for public ears and eyes, as Beate
48
Mattingly, Renaissance Diplomacy, p.115
49
Paul M. Kendall and Vincent Ilardi (eds.), Dispatches with Related Documents of Milanese Ambassadors in
France and Burgundy, 1450-1483, vol I: 1450-1460 (Athens, Ohio, 1970), p. 368
50
Mattingly, Renaissance Diplomacy, p. 114
51
Kendall and Ilardi, Dispatches with Related Documents of Milanese Ambassadors, p118
52
Kendall and Ilardi, Dispatches with Related Documents of Milanese Ambassadors, p. 346
53
Queller, The Office of Ambassador in the Middle Ages, p.140
54
“[...] avisarce tanto particularmente quanto te sia possible de ogni occurencia; et le cose importante vogli
metterein zifra, l’altro porray scrivere desteso.” As quoted and translated in: Kendall and Ilardi, Dispatches with
Related Documents of Milanese Ambassadors, p. 360
55
Jucker, “Trust and mistrust in letters”, p. 223
Page | 11
Körber argues. Michael Jucker warns, however, that this is a too strict division to use.56
Angelo Acciaiolo replies to the Duke of Milan in one of his reports that many things of great
importance have happened, but that these are too detailed to be put into writing.57
In the fourteenth century cipher and code developed into a separate craft. The
secretary to pope Clement VII, Gabrieli di Lavinde, designed a new kind of cryptography in
1349, the nomenclator. In this system not only individual letters are substituted for another
letter or symbol, but also complete words have their individual counterparts in the cipher
alphabet. In 1401 the next step is taken: the use of multiple cipher alphabets, used by the
Duchy of Mantua. In this type of cipher there is not only one letter that stands in the place of
another, but several letters stand in the place of one. This increases the amount of possible
solutions.58 From this point onwards cryptography really begins to grow: at the turn of the
15th century secular authorities regularly begin to use this technique to hide the meaning of
their writings.
At the end of the 15th century the reports by ambassadors are standardized as an
obligatory part of their correspondence with the homeland, the earliest example stems from
1492 which requires that a report contains information on the income of a lord, the military
preparedness of his realm, the enemies of the lord/king and alliances and parties at court. This
relazione was to describe these things both about his final destination and about the cities he
travelled by which did not have a resident ambassador of his own country59. This is the kind
of information a lord would want to hide in times of war and enmity. One wonders how far
the ambassador could complete his relazione without the help of spies. It seems as if the
ambassador by now has become a centre of information to and from states, laundering secrets
obtained by illegal means into official reports, written by the legal person of the ambassador.
Not only letters were used for communication though: The Earl of Warwick made sure
that Robert Welles knew when to get into action at the eve of the Lincolnshire rebellion in
1470 by sending him a golden ring.60
I already mentioned the requirement that the relazione be written in the ambassador`s
own hand. Apparently there is some kind of veracity-check on these documents, mimicking
the signature or a watermark which ensures the reader that it is the real deal, as things can get
56
57
Kendall and Ilardi, Dispatches with Related Documents of Milanese Ambassadors, p. 44 and again in the letter
on p. 60.
58
59
Queller, The Office of Ambassador in the Middle Ages, p.147
60
Page | 12
terribly wrong. In the already mentioned conflict between the king of England and Warwick
at the time of the Lincolnshire Rebellions in 1470 the dukes Clarence and Warwick, still
pretending to be in league with King Edward IV, sent him false letters which “betrayed” their
positions in his defence while in fact they had been preparing their armies elsewhere for an
attack on him.61
One has to be absolutely sure of the sources of information, especially when matters of
personal trust are at stake: an ordinance from Venice to the orator (ambassador) in Rome in
1478 asks for an autograph. The Venetian council had heard that Venetian secrets were told in
Rome; hence they asked their man in Rome to write in his own hand who wrote what to
whom. Also, to prevent more secrets from falling in the wrong hands, he was to burn his
letters and registers.62 The command to burn documents is not unique: it occurred in times of
danger that ambassadors were asked to destroy their documents.63 Mantua had another
solution for this problem of confidentiality. In 1340 they asked their ambassadors to send
messages only with Mantuan messengers.64 Milan too made use of messengers who were
personally known by the sender, to bring letters home safely.65
As the age of written culture steadily advances, so do espionage practices. Identity has
become something which can be deduced not only from personal observation, but also from
items which serve as a mark of identity such as seals. These were occasionally to be collected
as evidence that one person or another was present at a meeting at which the spy was to obtain
intelligence.66 Henry VII wished to know what Warwick, the later Richard IV, was discussing
with Margaret of Burgundy in Malines, and how he did so. Thus he sent three spies to
Malines to find out the identity of Warwick`s correspondents. They returned with the men`s
seals.67 Henry also sent three men to Richard’s court under the pretence that they had been
banished by Henry. They managed to gain so much trust that Richard made them his
councillors; but in secret they kept an eye on everything that went on. One day their patience
was rewarded: Richard had received letters in which great men from England promised him
their allegiance, and to be sure they also attached their seals. The three spies quickly sent
word to Richard, who warned his man in Calais to fetch the seals and bring them to him as
soon as possible. With these seals the king could identify the conspirators and had them
61
62
63
64
65
Kendall and Ilardi, Dispatches with Related Documents of Milanese Ambassadors, among others p.150
66
67
Arthurson, “Espionage and intelligence”, p.138-139
Page | 13
punished.68 This is a very interesting case, as the correspondent of Warwick is not identified
by word of the spies, but by the return with seals. The use of seals is more than a means of
authentication; it is as if the correspondents were caught red-handed in the act of conspiracy
against the king. The seal represents not just the consent of the subscriptor to the message but
his very presence in the conveyance of the message.69 It is difficult to judge how common it
was for spies to obtain seals as evidence of participation by a certain person in a conspiracy,
as I have found no other case. This doesn`t mean that this is an isolated case, though, as few
specific espionage cases have been recorded in the sources.
68
J.A. Buchon, Collection des Chroniques Nationales Française’s, tome XLVII, chroniques de Jean Molinet
tome V (Paris 1828), chapter CCLXXXIV year 1495, pp. 47-48
69
Peter Worm, “From subscription to seal: the growing importance of seals as signs of authenticity in early
medieval royal charters” in: Petra Schulte, Marco Mostert and Irene van Renswoude (ed.), Utrecht Studies in
Medieval Literacy 13: Strategies of Writing, Studies on Text and Trust in Medieval Europe (Turnhout 2008), pp.
71-74
Page | 14
The 16th century and further

From the beginning of the sixteenth century the resident ambassadors entered the
game of politics. Their function was to aid special ambassadors who were sent by the king
with a special diplomatic mission and tell them on arrival the ins and outs of court.70 Duke
John V paid two men by the names of Langeffort and Le Meignen since 1406 to reside in
Westminster so that in 1413 the Breton ambassador who went to the court of Henry V could
contact them and be updated on how matters stood.71 Besides these resident ambassadors,
ambassadors always had contacts with non-officials who lived permanently in the areas they
were to start negotiations in.72
Of course everyone knew the double use which could be made of ambassadors, and
ambassadors were treated with due suspicion by their hosts. An example of this double nature
of ambassadors and the enemy`s response is what happened in the summer of 1415 in
England. Henry V had plans to invade Normandy, and the French found this out. To check
how much of this rumour was true, they sent out ambassadors for a final round of
negotiations. As the ambassadors saw how far the plans of the English had advanced, they
tried to sneak away to get the news as soon as possible to their masters.73 One might ask
oneself if these ambassadors really were sent out for negotiations in the first place...perhaps
the English thought the same, as the men were caught as they slipped away, thus preventing
them from leaving and bringing early news of the invasion. Here the ambassadors themselves
were closely observed, but intercepted letters could also give information on the real mission
of an ambassador. In 1453 Angelo Acciaioli had caught some letters to the advisors of Sicily.
In these letters he reads to his own amazement that the writer in Avignon has a suspiciously
detailed idea of his instructions.74 Who found his instructions, and sent them to Avignon to
Sicily`s correspondents? Things went wrong more often even if letters were ciphered. Another
Milanese ambassador, Tomasso Da Rieti, warns the Duke of Milan that the letters sent to him
may have betrayed their contents: “Pietro da Sesto, courier, has reached me here with letters
from Your Lordship, which he delivered all opened. He says he was detained for seven days
by the Duke of Savoy, and it is very likely that they have deciphered the letters if they have
70
Behrens, “The office of the English resident ambassador”, p. 162-165 and Mattingly, Renaissance Diplomacy,
p.64
71
72
Alban and Allmand, “Spies and spying in the fourteenth century”, p.79
73
74
Kendall and Ilardi, Dispatches with Related Documents of Milanese Ambassadors, p. 120
Page | 15
anyone who knows how to do it.”75 To protect the letters they were carrying, and in order for
the letters to reach their destination, ambassadors did not mind using tricks. In 1509 the court
of Spain sent ambassadors out to Calais and England. In order to get there they had to cross
French territory, which was a bit of a problem, as the French were not inclined to cooperate in
alliances between England and Spain. Thus the ambassadors pretended they carried letters for
Margaret of Savoy. Once arrived in Savoy they changed their course to Calais.76
In all their scheming and collecting of information and especially the information they
were not to receive ambassadors need ways to communicate their findings to their masters.
Here cipher really begins to develop into a convenient tool. Though in the 15th century the
basics were laid, over time cipher systems grew more and more complex, to such a degree
that in the 16th century full-time cipher secretaries were employed.77 In 1452 Angelo Acciaioli
sent a letter to the Duke of Milan, stating that: “Letters from Genoa arrived here, written to
Master Francesco of Alessandria, before I had deciphered yours- letters containing the news
of the making of the league and giving not only the public clauses but also, quite openly, the
clause that, Your Lordship wrote me, were secret. For good reason I withhold the name of the
man who writes from Genoa, but I know well who the writer was.”78 This small quote reveals
a world of secret communication. The Duke of Milan sends letters both in cipher and in plain
text to his ambassador. The plain text is public, can be read out to anyone whom it may
concern, but the cipher text is secret though not so secret anymore, as someone from Genoa
wrote these clauses in plain text. Luckily though, these letters were intercepted so that Angelo
could warn his master that what once was secret is secret no longer.
Between 1490 and 1510 England really got into using cipher, but this is 50 years after
Italy got the hang of it.79 This difference of a half century is not strange: Italy was ahead of
the rest of Europe in establishing bureaucracy and the intensive use of written documents.
That cipher comes along in this increase of written material is not strange. But now, in the
fifteenth century, when written culture is increasing rapidly in Europe, complete trust in
75
“É arivato qui da mi Petro Da Secto, cavallaro, cum lettere de la S. V., el qualle le ha portate tutte aperta; et
dice essere stato VII dì destenuto [sic] dal Duca de Savoya. Verissimile é debano havere cavato le zifre, se hano
ch’il sapia fare.”As quoted and translated in: Kendall and Ilardi, Dispatches with Related Documents of Milanese
Ambassadors, p. 145
76
77
78
“ Qui furono littere a Genova scripte a Maestro Francesco D ‘Allexandria, Avanti ch’io havessi diciferate le
vostre, nelle quail contiene la lega come é facta, et non sole le cose publice, ma assai apertamente quelle che la
S.ria Vostra mi scrive essere segrete; et per buona cagione dimetto il nome di chi scrive da Genova, ma io so
bene chi fu lo scriptore.” As quoted and translated in: Kendall and Ilardi, Dispatches with Related Documents of
Milanese Ambassadors, p. 54
79
Page | 16
written communication has not taken complete sway in politics yet. As late as 1499 an envoy
in Schaffhausen still asks his colleague Hans Tecktermann to take a message along with him
back to Freiburg as he does not dare to put the information he wishes to send home in a letter.
Instead he makes use of personal relationships and oral communication.80
80
Page | 17
Conclusion: Emergence of cipher, espionage and more secrets

The history of cipher as discussed in this paper could be summarized as follows. In the
early Middle Ages cipher was rarely used for diplomatic or military purposes; starting around
the 14th century there seems to be a change, and within a century cipher is used for military
and diplomatic practices all over Europe. The aim of this paper is to explore how this
happened, and most importantly to understand what set this process of change in motion. The
central question in the complex of factors and interests which are dragged along in this
process concerning the emergence of cipher is: how does one obtain and keep power? In this
case power is obtained through knowledge, knowledge both in the battlefield and on the field
of politics. When it concerns the battlefield scouts are used, and in politics spies are the
people who keep eyes and ears in places where they are not supposed to be. Both, though at
work in different contexts, have the element of secrecy in common; they both try to discover
what should remain hidden from the enemy’s eyes. In this seemingly simple division of tasks
the emergence of diplomacy changes the situation as it was in the early Middle Ages. I have
been asking what set this development into motion, what had caused these changes in the
fields of espionage and the manners in which spies communicated? The answer lies in two
areas: the ways in which politics and war were conducted changed and asked for new
methods, and the development of writing and a different use of the written word in society
opened new ways of communication.
At the same time as diplomacy and the office of ambassador arose in politics,
confidence in the written word grew and methods were looked for which enabled the
parchment to keep its secrets as well as a tight-lipped messenger would. Cipher, first used in
games and magic, was now used for different purposes. Other security measures were being
taken as well, such as the requirement of autographs, the burning of archives and the use of
tokens. However, amidst all these sealed envelopes and mysterious scribblings, oral
communication was still considered a safe, if not the safest, manner in which sensitive
information could be conveyed.
A last remark I would like to make here, or rather a concern which I share with Paul
Dutton: now that we have taken a look at the tip of the iceberg of medieval secrecy in
diplomacy, it seems that a new world arises next to the familiar one medievalists have studied
for so long. Dutton wonders how far we can go in saying that we understand medieval culture,
Page | 18
if we do not try to pry open this hidden world. He ends his article on secrets at Carolingian
courts with words which hit the spot exactly, and I would like to repeat them here:
“We dance around in a ring and suppose,

But the secret sits in the middle, and knows”81
81
Robert Frost, as quoted by Paul Dutton “Keeping secrets in a dark age”,p. 187.
Page | 19
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Trust in Untrustworthy

Early Middle Ages

14th and 15th century: origins of cipher and growth of

The 16th century and further

Conclusion: Emergence of cipher, espionage and more secrets

“We dance around in a ring and suppose,

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