This article analyses the dynamics that were present in the manner of representing the Lithuanian and Ruthenian legacy of Ladislaus Jagiello and of the first two generations of his descendants in popular 16th-century pictorial catalogues of Polish monarchs. The catalogues actively supported the collective memory and facilitated the integration of Lithuanian and Ruthenian traditions in the Kingdom of Poland. An analysis of the textual and visual message of Maciej of Miechów’s Chronica Polonorum (1519, 1521), of the treatises by Justus Decius appended to it in 1521, the illustrated chronicles of Marcin (1551, 1554, 1564) and Joachim (1597) Bielski, and the visual contents of Tomasz Treter’s Regum Poloniae icones (1591) series has shown that a typical feature of 16th-century works on the first Jagiellons is the non-uniformity of their literary narrations, which contrasts with the relatively stable image of the Jagiellons in the pictorial catalogues. The textual narratives were much quicker to react to the current political, cultural and confessional needs than their visual counterparts, and they accordingly adjusted the literary image of the first Jagiellons. In the dynastic narrations the unfavourable image of the Jagiellons, still present in the first two decades of the 16th century, was replaced by a laudable narrative concerning the predecessors of Sigismund the Old, which brought into prominence the dynasty’s ancient lineage and its contributions to the Kingdom of Poland. The Eastern roots of the Jagiellons were assimilated into the Polish historical representations by crediting the Lithuanians and Ruthenians with a Sarmatian genealogy. The narratives of the nobility dating from the second half of the 16th century associated the dynasty’s history with that of the nobility and presented it in the light of the religious, heraldic and socio-ethical interests of Polish noblemen. Ladislaus Jagiello was therefore depicted as a leader of the Polish and Lithuanian nations, operating at the intersection of two diverse cultures, i.e. cultures which were not subject to any evaluative assessment unless they were detrimental to Polish traditions and interests. The last discussed pictorial catalogue, i.e. a series of depictions of monarchs by Tomasz Treter, is a rare example of reaching back to Jagiello’s Eastern heritage by choosing a Ruthenian painting as a model for his depiction. The use of a Ruthenian representation of the king from all the paintings funded by Jagiello is proof of interest in the Eastern artistic tradition and of its gradual integration into the cultural heritage of the Crown on the eve of the Union of Brest (1596).