This study highlights the history of a character from the perspective of the portraits depicting him: the great chancellor and knight Anastasie Bașotă. He was one of the richest philanthropist boyars in Moldavia and he served as a minister of Public Works. He was the one who founded on the Pomârla estate (a village situated 15 km north-west from Dorohoi) the first private rural school (1838) and an academic institute (1878). At the same time, the boyar can also be seen as a constant commissioner for the painters in the Moldavian Principality, through the great number of paintings that he owned in his houses of Iași and in his mansion of his country estate. From these galleries of paintings, only a couple of images were preserved that represent the boyar. Hence, the collections of the Art Museum “Ion Irimescu” of Fălticeni host a portrait made by Nicollo Livaditi, which was the first work by this Italian painter upon his arrival to the Moldavian capital (1830). Anastasie is depicted while he served as a hetman, clad in European attire, with the St Anna decoration conferred by Russia. The second Biedermeier-style portrait, made by an unknown painter, is preserved in the “Pentecoste” church of Cucorăni (commune of Mihai Eminescu, Botoșani county), one of his foundations. The panting is a founder portrait and it was made in 1856, when the church was finalized and then dedicated. The boyar, who had the position of chancellor, is depicted in his uniform of minister of Public Works, with the order of St Anna (third class civilian), St Stanislas second class commander (tie), awarded by the Tsarist Empire, and the order Nișhan- Iftihar (The Order of Glory) conferred by the Ottoman Empire. The photography taken in a Parisian studio and reproduced on a postcard features Anastasie in his older days, dressed in a redingote, with a big moustache, wearing on the chest a ribbon with the miniatures of decorations. Besides the images taken during his life, it is worth noting two posthumous portraits: a wall painting made in 1887-1891 on the western wall of the church in Pomârla; the other one, an academic-style oil canvas, is stored in the church of Hilișeu-Cloșca, both localities in the Botoșani county. In the two founder paintings of Cucorăni and Pomârla, it may be observed that the path followed by the artists in mid 19th century is opposite. They start from the salon portrait for the founder portrait and not the other way around. In order to match the place destined to host the painting, namely the necropolis-church, the characters taken from the easel painting are slightly ranked – a specific of “primitive” painters, hence the votive scene acquires a “sacred character”, “because it depicts persons in front of the divinity”. The three images of Anastasie Bașotă taken during his life, which are also the most authentic sources regarding the boyar’s appearance, point out the phases in his life and career: the first painting, signed by Nicollo Livaditi, displays him as a hetman; the second painting, made by an unknown painter, marks the period when he was a chancellor and the minister of Public Works.