The study presents historical documents from the collection of the scholar-bishop Ghenadie Enăceanu, held at the Library of the Romanian Academy, with a focus on charters adorned with miniatures issued by Matei Basarab, Grigorie I Ghica, Radu Leon, Gheorghe Duca and Constantin Brâncoveanu in the 17th century. The analysis combines the legal and socio-economic content of the documents with an examination of their miniature decoration — plant, zoomorphic and iconographic motifs, as well as votive portraits — highlighting the links between chancery art and the miniatures found in religious manuscripts from Wallachia.