Russian painter Vasily Vereshchagin, who had a worldwide reputation during his lifetime, is known for his realistic attitude and choice of subjects from an Orientalist perspective. On the other hand, he is among the closest witnesses of Russia’s expansion toward Asia. Since he officially accompanied the Russian military mission and was tasked with illustrating/documenting the occupied regions in all details, he had the opportunity to observe some Asian lands closely in those years when the issues of “Easternness”, “Westernness” and identity were the subject of debate among the Russian intelligentsia. Written sources of those years indicate that a significant value was attributed to Turkestan and Samarkand, among all the occupied lands in Asia. Because, as it is known, Samarkand has been the leading center of Central Asia and Islamic cultures since the Middle Ages: The capture of Samarkand, which includes the memory of Timur, one of the legendary leaders of the medieval Islamic world, and the magnificent Timurid monuments, was seen as an important gain for Russia at that time, not only expanding its territory but also with its cultural connotations. Having a geopolitical and symbolic significance for both native residents and Western narratives, Samarkand has undoubtedly been privileged to some extent in terms of culture and administration among these newly captured lands by Russia. On a larger scale, Samarkand has also become a showcase for Russia in the colonization process: Preserving, restoring, documenting, and exhibiting the “legendary” architectural heritage of Samarkand, which was undoubtedly one of the most interesting cities of the East thanks to the repetitive narratives since the Middle Ages, has been a subject that Russia has meticulously focused on since the first years of their domination of Turkestan. From the very beginning, scientific expeditions were organized with the participation of experts from different disciplines and in addition to the geographic or ethnologic research, they recorded the local architecture with many photographs and paintings in all detail and prepared comprehensive albums in this context. Vereshchagin’s realistic style and almost photographic attitude must be the main reason why he was chosen among the other war painters of the period to create a visual archive of the region. Looking at his paintings, it can be said that they almost have a “documentary” flavor rather than a desire to bring artistic innovation. In his Turkestan series, including scenes of Samarkand, besides the depictions of architecture and urban history, there are also daily life scenes, some war and front views, or scenes pointing to the poverty and misery of the local people. But in the context of cultural heritage, it should be emphasized that Vereshchagin’s interest is not just a “documentary” or “scientific” attitude or even an artistic enthusiasm. All these scenes can be interpreted, on a larger scale, as a manifestation of Russia’s efforts to legitimize its colonization process at the international level. Suggesting that Russia has protected the historical and ethnographic values of Turkestan, these paintings were exhibited in many Western countries, accordingly, they can be regarded as an attempt to legitimize the expansion of Russia’s dominance in Central Asia, implying a “civilizing” mission in the occupied lands. This whole process also gives us clues about the dynamics of Russian Westernization. Therefore, Vereshchagin’s paintings can be interpreted as significant visual documents to understand the debates of that period, as well as their artistic values. Certainly, the documentation and preservation of the Timurid monuments in those years were carried out mainly with a political mission; however, it should be emphasized that all these activities ensured the survival of the monuments. Vereshchagin’s Samarkand scenes reflect the appearance of the monuments with a clarity and vitality that photographs could not offer at that time, in this sense, they can be described as important visual documents in terms of art history. In this context, in the first part of this paper, the symbolic importance that the Russians attributed to the East, and more specifically to the Turkestan/Samarkand region during the colonization process is discussed. Then, on this basis, the appearance of the Timurid monuments in the 1870s is examined as documented by Vereshchagin and compared with other sources. When his paintings are compared with the photographs in the Turkestan albums prepared in the same years, they also contain some differentiating details. For example, in some of his paintings, it is seen that he made some attempts to “complete” the damaged parts of the buildings. Another remarkable detail is that a rather large painting from the Turkestan series about Timur’s tomb was presented to the Turkish Republic as a gift by the Soviet delegation much later, during the Stalin era. It can be thought that a painting depicting Timur’s tomb was carefully chosen as a diplomatic gift because such a theme reminds both of common historical ties and Russia’s power and dominance in the region. The presentation of this gift to Turkey, which is exhibited in the State Museum of Fine Arts (Ankara) today, is also discussed in this paper based on Turkish and Russian documents and newspapers of that period. To sum up, in this article, Vereshchagin’s paintings are examined both in their context in Russian orientalism and to record the Timurid architectural heritage visually as a document.