CAPTIVES, DIPLOMATS AND SPIES: THE EXTRAORDINARY CAREER OF A

TRANS-IMPERIAL GO-BETWEEN, BARTOLOMEO BRUTTI (1570s-1590s)

Emrah Safa Gürkan
Istanbul 29 Mayis University

For long Ottoman historiography has been plagued by a state-centric approach, mostly
due to the source base. The Ottoman archives in Istanbul contain official documentation
which was issued from the chancery of the central government. These official documents
contain a certain degree of rhetoric and are rather formulaic; they thus reflect very little on the
practical realities of political and diplomatic life in the Ottoman Empire.
By relying on documentation from Spanish and Venetian archives, this presentation
will try to overcome this “formality” that has constrained diplomatic historians of the
Ottoman Empire to reproduce official documentation and their formulaic statements. I will
aim to accentuate the multiplicity of actors that were involved in daily politics and vernacular
diplomacy in sixteenth-century Istanbul and demonstrate how beyond the calculated realm of
official diplomacy lay a much more interesting world with interest-seeking actors most of
whom are carefully looked over in government documentation and official Ottoman histories.
By concentrating on a specific ransom agent named Bartolomeo Brutti, I will not only show
how cross-confessional diplomacy, ransoming, and Ottoman factional politics were
intertwined, but also demonstrate how cultural intermediaries with trans-imperial life
trajectories (a useful term borrowed from Rothman) 1 mediated religious, cultural and
linguistic boundaries and connected two empires at each other’s throats, the Ottomans in the
eastern Mediterranean and the Habsburgs in the western Mediterranean.
The protagonist of the presentation is a Venetian subject named Bartolomeo Brutti,
coming from an Albanian family based on Ulcinj. Bartolomeo’s father was a cavalry captain
in Venetian employ. Bartolomeo followed his lead by entering in Venetian service as a
giovane di lingua, one of the apprentice dragomans (interpreters) that the Venetians were
trying to educate in their bailate (embassy) in Istanbul in order not to heavily rely on not-so-
trustworthy local interpreters. Even though he soon would quit his job, his two short stint in
the bailate allowed him to grasp the realities of political life in Istanbul and familiarize
himself with the imperial elites as well as several European diplomats and captives in the city.
It was these connections which allowed him to play a key role in the liberation of prisoners-
of-war that fell in enemy hands in the Battle of Lepanto (1571) where the Ottoman fleet
suffered a disastrous defeat at the hand of the Christians.
We do not know why he was chosen for this task, but Bartolomeo was the
intermediary in the exchange of Muslim and Christian prisoners-of-war, made possible by the
peace agreement between the Ottomans and the Venetians in 1574. Bartolomeo traveled to
Rome in 1575 in order to carry 34 Ottoman prisoners-of-war in Italy, including two sons of
the martyred Ottoman Grand Admiral Müezzinzade Ali Pasha, as well as governors and other
important officials, first to Fermo, and then to Ragusa where the Ottomans would dispatch to
Ragusa the Christian captives who had fallen captive in Nicosia, Famagusta and Tunis.
Leaving aside the captives’ political importance and social prestige, this could seem one of
those routine cross-confessional prisoner/captive exchanges generally undertaken by men of
both worlds, go-betweens/intermediaries, with connections on both sides of the porous
frontier between Islam and Christianity. However, this was not the case as the young
Bartolomeo demonstrated his skills in diversifying his activities and ingratiating himself with
both Ottoman and Habsburg elites. When he returned to Istanbul, he tried his chance, one
more time, in the bailate as a giovane di lingua, but resigned once again seven months later.
1
E. Natalie Rothman, Brokering Empire: Trans-Imperial Subjects between Venice and Istanbul (Ithaca: Cornell
University Press, 2012).
 This was a fortunate decision as his connections and acumen would bring new
opportunities. During his visit in Italy, he had established close connections with Habsburg
authorities and provided them with information regarding military preparations and the
political situation in the Ottoman capital; this information helped his recruitment by the
Habsburg secret service. Moreover, he engaged on their behalf in secret dealings with one of
the Ottoman officials whom he liberated from Christian hands and accompanied until Istanbul
in 1575: Mehmed Pasha, the son of the famous Ottoman corsair Salih Reis. Even though he
had once attained one of the most prestigious posts of the Ottoman naval establishment,
governor-generalty of Algeria (a post occupied by his father in the past), Mehmed Bey
realized soon after his return from captivity that he fell out of favor. Bartolomeo and he
teamed up in order to offer the Habsburgs an interesting clandestine project: If Philip II could
lend Mehmed Pasha 30.000 ducats, then the disgraced corsair could use this money in order to
bribe the Grand Vizier Sokollu Mehmed Pasha and recover the governor-generalty of Algeria.
He could then submit Algeria to Philip II’s will and become his vassal. The port of Algiers
was the major Ottoman corsair nest in the Western Mediterranean and the province of Algeria
was the most important Ottoman province in the region. Thus, this was not the first time that
such an offer was contemplated; the Habsburgs had entered into negotiations of defection
with other prominent Ottoman naval commanders such as Grand Admiral Barbaros Hayreddin
Pasha and the Governor-General of Algeria Hasan Pasha through go-betweens like
Bartolomeo. Yet, Bartolomeo’s plan was not confined to Algiers alone; it pretended to change
the balance-of-power in North Africa for good in Habsburg’s favor. Once Mehmed Pasha
secured the governorship of Algeria and submit this corsair nest to Philip II, the second part of
the plan would be to form an anti-Ottoman coalition including the Moroccan prince
Abdulmelik. A pretender to the Sa’adi throne, he had sought refuge in Algiers and there
become a close friend of Mehmed Pasha, then the Governor-General of Algeria. By the time
Bartolomeo appeared in Naples, in order to undertake these negotiations of defection, the new
Governor-General of Algeria, Ramazan Pasha, had already put Abdulmelik on the Moroccan
throne as an Ottoman vassal. Thus, what was at stake was an alliance between Algeria,
Morocco and the Habsburgs, an alliance which would eradicate Ottoman presence from the
region. Mehmed Pasha also sought the assurance that, in case the plan failed, he be allowed to
settle in Sicily where he would live as a Muslim.
While Bartolomeo was in Naples with these offers in 1576, he met with a Habsburg
agent named Martin de Acuña, a Spanish knight from Valladolid and formerly a slave in
Istanbul. He was travelling to Istanbul with a sabotage plan that targeted, unsurprisingly, the
Ottoman Navy and the Arsenal. Having learned of the plan, Bartolomeo vehemently opposed
it with a number of interesting points that shed light on the feasibility of such plans that these
spies offered the authorities over and over again as well as Bartolomeo’s knowledge of local
conditions in the Ottoman capital. According to him, it was already too late in the season and
that Habsburg saboteurs would never arrive in Istanbul on time. When they did, all the galleys
would be on water and not on land as de Acuña believed. Moreover, Bartolomeo accentuated
the impossibility of acquiring artificial fires without being discovered given that the
production of these materials was in the hands of a limited number of people. Likewise, it was
impossible to get close to the galleys as the Arsenal was well-guarded at all times by patrols
of small boats (caicchi) and it was prohibited to sail into the Golden Horn after “the second
hour of the night”. De Acuña’s plan to ransom slaves in important positions could not be
realized either as it was impossible to ransom them with money; the only possible way was to
exchange them for Christian slaves. His contacts among Grand Admiral Uluc Ali’s men were
useless as well. His main liaison, a Venetian renegade named Soliman Veneziano, was
inexperienced and others should not be trusted. Most of Uluc Ali’s renegades generally
wanted at first to return to Christianity; but when their enthusiasm, colera, passed, they
changed their minds and started accusing anybody who negotiated with them. Bartolomeo did
not only enumerate the possible impediments, but also left his own version explaining under
which circumstances such a plan of sabotage could be realized. With the knowledge of a
handful of people, everything had to be carefully planned and executed on a gloomy night in
December when the galleys were taken to land and the Arsenal was little guarded because of
the cold weather, snow and wind.
Bartolomeo’s arguments could not dissuade the authorities and de Acuña left for
Istanbul. Unable to undertake his mission, de Acuña was detected by the Ottomans. In an
interesting episode where espionage and diplomacy quickly became convoluted, de Acuña
came up with an interesting lie in order to save his skin: through the Habsburg spymaster in
the Ottoman capital, Aurelio Santa Croce, he informed the Ottoman authorities that he was
not an enemy spy, but a diplomat sent by the Habsburgs in order to negotiate a truce with the
Ottomans. Thanks to an imperial diploma forged from a letter which Philip II sent to powerful
Jewish power broker Joseph Nasi and with the help of local Habsburg agents and informants
within the Ottoman administrative and military mechanism, he succeeded in persuading the
Ottoman Grand Vizier Sokollu Mehmed Pasha who declared a one-year truce and send de
Acuña back in order to ask for an official ambassador. Also desiring a respite from a costly
war, Philip II accepted the fait accompli and decided upon a Milanese named Giovanni
Margliani, also formerly a slave in Istanbul, as an unofficial envoy that would resume
negotiations. Margliani and Bartolomeo knew each other from Istanbul as Bartolomeo
Margliani’s uncle, Gabrio Cerbelloni, was among the prisoners-of-war in 1575. Already on
good terms with the Habsburg authorities, Bartolomeo secured himself a spot in the
negotiations; he would assist on the one hand Margliani with necessary local connections and
knowledge of Ottoman diplomatic protocol and on the other continue negotiating with
Mehmed Pasha for his possible defection. In addition to ransom agent, spy and secret agent,
Bartolomeo now added diplomat to his occupations.
Margliani and Bartolomeo arrived in Istanbul in late 1577 and quickly started
negotiations that would end in a three-year truce in February 1581. However, the duo quickly
fell out with each other. Margliani’s correspondence is full of complaints about Bartolomeo’s
bad intentions, while Bartolomeo, frustrated with Margliani’s efforts to exclude him from the
negotiations, devised a couple of interesting plans to get rid of his colleague.
First, he told Margliani that Grand Vizier Sokollu was angry with him because the
official Habsburg ambassador, Juan Rocaful, had not arrived as was announced and that he
should ask from Sokollu license to leave Istanbul. If he did not allow him to leave, then they
would ask the Sultan when he left the capital for hunting. There Bartolomeo could talk in
Albanian with the Sultan’s men so that Sokollu could not understand what he said. If this did
not work either, then he would secretly take him to Anatolia from where he could pass to
Chios and then to freedom. When Margliani kindly but astutely rejected the offer, Bartolomeo
informed the Grand Vizier that Margliani was contemplating to escape and added that Rocaful
was not coming because the Habsburgs were planning an expedition against Algiers. When
Ashkenazi broke the news to him, Margliani was appalled by this “greatest betrayal of the
world”.2
Rest of Bartolomeo’s story is indicative of the realities of Ottoman factional politics.
Bartolomeo quickly alienated everybody including the Grand Vizier and found himself busy
with other problems that closed one page in his career, but opened another. His activities were
by no means restricted to espionage, diplomacy and slave ransoming; he also directly
participated in Ottoman court politics. He was a relative of the rival of Sokollu, the Albanian
Sinan Pasha; he was probably his cousin. Furthermore, he acted as an agent of the Moldavian
prince Iancu Sasul who was seeking to acquire the crown from Rhodes where he was kept by
2
AGS, E 1080, fols. 44 and 46 (both 4 July 1579).
the Ottomans in exile. Bartolomeo’s machinations against the reigning voivode, a client of
Sokollu, had already infuriated the Pasha. When he furthermore learned that Bartolomeo lied
to him on several occasions, he had him imprisoned. Margliani then found himself in an
awkward position because he was obliged to defend Bartolomeo in compliance with the
instructions that he had received from Philip II before undertaking his voyage. Furthermore,
he feared that Bartolomeo might convert to Islam in order to save his skin and confess the
details of negotiations for Mehmed Pasha’s defection. He sent Ottoman grand dragoman
Hürrem Bey, also a Spanish informant on payroll, to the Grand Vizier and argued that
Bartolomeo came with him and therefore, as a part of his mission, should be treated with
respect, no matter what he did. If he was executed, the negotiations could not proceed.
Meanwhile, Sokollu had already made his case in front of the Sultan who ordered that the
Albanian should be impaled. Sinan Pasha, as the recipient of 8.000 ducats that Bartolomeo
secured from Iancu for the Moldavian throne, knew that Sokollu’s real target was none other
than himself. He quickly submitted a petition (‘arz) to the Sultan, arguing that Sokollu was
trying to punish Bartolomeo because he was involved in factional politics. In order to
convince the Sultan that Bartolomeo was a Habsburg spy, Sokollu even went as far as to forge
a letter written by the Viceroy of Naples who thanked the Albanese for the information he
sent. Sinan then made another ‘arz, arguing that Sokollu’s man, the Jewish power broker and
physician Salomon Ashkenazi, deceived Margliani into submitting a document (scripture)
which, although used as a proof to Bartolomeo’s culpability, should be given no credit.
Sokollu then agreed to release him with the condition that he should immediately leave for
Naples where he would be punished by the Viceroy. Bartolomeo was told that he was going to
welcome the incoming Habsburg ambassador Rocafull. He met in Ragusa with Habsburg
agents Giovanni Stefano de Ferrari and Antonio Echevarri who informed him that this was a
ruse and Rocafull was not coming. He tried to return with the two to Istanbul; yet the
authorities forced him to return to Ragusa from where he was put, on Sokollu’s orders, on a
ship that set sail for Barleta. Unfavourable winds saved Bartolomeo from a compulsory trip
which might have been the end of his career as a power broker in the Ottoman capital. When
his ship had to take refuge in a Ragusan island, he easily passed to a nearby Venetian island
and from there to Alessio in his native Albania. There he was once again detained by the men
sent by the Ragusan authorities upon the instigation of Margliani.
In the meantime, however, the balance-of-power in Istanbul changed decisively after
the assassination of Sokollu and the consequent purging of his faction. Upon learning
Bartolomeo’s detention, Sinan Pasha’s sister sent one of her sons with 25 men to recover his
relative by force and take him to the Ottoman capital. The brother Christoforo Brutti, also a
giovane di lingua in the bailate, and a chaus sent by Sinan Pasha arrived in Alessio with an
imperial order for Bartolomeo’s release. Unable to find him in the city, the chaus arrested the
Ragusans who detained the Albanian at the first place.
As soon as he returned to Istanbul, Bartolomeo at once resumed his machinations
against Margliani. He first contacted Grand Admiral Uluc Ali, the ardent opponent of the
truce who was looking for any excuse to hamper the negotiations. Then he told the new Grand
Vizier Ahmed Pasha that Margliani’s real mission was to buy time rather than to sign a truce.
Furthermore, via one of his men in the baño, the lodgings of the Christian slaves working in
the Arsenal, he spread the rumour that Margliani usurped the money Philip II gave him for the
ransoming of Spanish slaves. The provoked slaves were almost making “ciertas
informaciones y poderes”, written statements against Margliani, if not for a certain Gaspar
Ligero who opposed to sign and even fought fist to fist with another slave. Fortunately for
Margliani, not only Bartolomeo’s machinations proved futile, but also he was set to leave the
Ottoman capital for Moldavia where he would become the high dignitary of the new voivode
Iancu Sasul whose nomination he adroitly brokered by using his connections in the Ottoman
capital and Sasul’s promise of large sums of money to Ottoman grandees.
Bartolomeo would have a thriving career in Moldavia as the most powerful statesman,
carrying several honorific titles and enjoying lucrative fiefs in the kingdom until his execution
by a hostile voivode, Aron Tiranul, in 1592. This part of his career is nevertheless outside the
scope of our presentation. Suffice it to say that he did not neglect his connections in the
Ottoman capital, most importantly those with his kin Sinan Pasha which would soon be the
Grand Vizier on several occasions (1580-1582, 1589-1591, 1593-1595, 1595-1596). He was
in Istanbul in 1582, as his prince’s envoy to the festivities for future’s Murad III’s
circumcision and carrying his presents for the Sultan. During this visit, he negotiated with
Sinan Pasha the deposition of Iancu with another pretender, Petru Schiopul, whom he
accompanied to Moldavia. When the former became Grand Vizier once again in 1589, he
would send his cousin Bartolomeo to Poland as an unofficial envoy (seemingly, he went there
as Petru’s envoy), thus entrusting him with a diligent diplomatic mission on the eve of a
possible Ottoman-Polish war. He would return to the Ottoman capital the next year with a
Polish envoy beside him and helped the finalization of a diplomatic agreement between the
two states.
As could be seen above, Bartolomeo Brutti wore several professional hats. He was an
apprentice dragoman working for the Venetian bailate, a ransom agent who negotiated the
century’s most important exchange of prisoners-of-war, an informant to the Spanish (on
payroll until 1586) and the Venetians (he provided his former master, the Venetian bailo, with
information after he quit his post in the bailate), an entrepreneur negotiating the defection of
Ottoman pashas and commenting on the feasibility of sabotage operations, a diplomatic
broker who helped Spanish and Polish ambassadors in Istanbul and a power broker heavily
involved in Ottoman factional politics through his kinship relation with Sinan Pasha. Such
small-time actors, whose exceptionally unorthodox careers were diligently censored by
Ottoman sources and could only be reconstructed by a careful investigation in different
European archives, played an important part in the daily conduct of cross-confessional
diplomacy, slave ransoming, governmental appointments and factional rivalries, the fields of
international and Ottoman domestic politics which were increasingly intertwined. Further
studies of similar entrepreneurial go-betweens who mastered the cultural codes of both
empires and who sought to capitalize on his trans-imperial connections in order to aggrandize
themselves will further elucidate the practical realities of vernacular diplomacy in the
Ottoman capital.
Our presentation moreover demonstrates the importance of kinship networks
throughout the Mediterranean and how these networks enabled diplomatic relations across the
religious divide between Islam and Christianity which some historians considered to have led
to irreconcilable hostility and a “clash of civilizations”. Familial, ethnic and linguistic
affinities created networks of trust necessary to form household and factions whose sphere of
action transcended religious, political and geographical differences. It was exactly these trans-
imperial connections that allowed Bartolomeo’s career to skyrocket from a young,
inexperienced, insignificant embassy dragoman, first to a ransom agent and a spy and then to
an influential diplomacy and power broker.

For more, see my dissertation, Espionage in the 16th century Mediterranean: Secret
Diplomacy, Mediterranean go-betweens and the Ottoman-Habsburg Rivalry, Georgetown
University, 2012, Chapter Five.