The dragoman apprentices of the Republic of Venice in Istanbul went through a long process of education that took at least a decade and then they became dragomans. Being a good-qualified dragoman required much more than that, maybe 30 or 40 years. The motto of a talented dragoman was “experience”. The experience of a dragoman included a very huge areas ranging from having the knowledge of the languages such as Italian, Latin, Turkish, Arabic, Persian, Greek and the Slavic dialects to absorbing the knowledges of the Ottoman society, traditions, laws and protocol rules. In this large area, the role of the elder and experienced dragomans was to guide the language boys and to prevent their lost in the Ottoman society and their loss of the Venetian traditions, the faith of Christianity and their fidelity to the Republic of Venice. This role prolonged the tenures of the experienced dragomans and caused the delay of their retirement while the dragomans and the language boys who lost their traditions, Christian identity and fedelity were dismissed by the authorities of the Republic of Venice. Another reason for the delay of retirement of dragomans was the absence of sufficient number of dragomans who mastered in the Oriental languages, notably Turkish, and in the fields of the mutual politics of the Venetian Republic and the Ottoman Empire, the negotiation subjects, the existing treaties and matters at the desired level. The number of the dragomans who knew the Ottoman judicial system well and who succeeded to establish good and solid relations with the Ottoman high officials in the long term was also low. Even the ailments and the health problems, as long as they were not fatal, could not head off this delay.