Theodora Palaiologina Kantakouzene Raoulaina was a wealthy educated patron, a true bibliophile with a rich collection of books, among which her autograph Vatican City, Biblioteca Apostolica Vaticana, gr. 1899 holds a prominent place. Raoulaina copied forty-three out of the fifty-three works of Aelius Aristides, a highly popular orator in the Palaiologan period for the teaching of rhetoric. The manuscript was copied most probably before 8 October 1273 and was intended to be Raoulaina’s gift to future generations. This chapter paper offers the first edition of hitherto unedited scholia to Aristides’ two Platonic discourses, Ὑπὲρ Ῥητορικῆς Λόγος Α΄&Β΄.

The chapter focuses on Manuel's reign in Thessalonike between 1382–87. It is argued that in contrast to his earlier despotate in Thessalonike, Manuel established a separatist reign that was in rebellion with Constantinople. Topics discussed include the siege of Thessalonike by the Ottomans, the emergence of Manuel's literary networks, the literary features of his letters from the period, his chief characteristics as a ruler and his intimate friendship with Demetrios Kydones. It is argued that Manuel's taxation policies further alienated the citizens from his cause, while his reign in Thessalonike also witnessed to his early clashes with ecclesiastics. Manuel's stance towards the Ottoman siege of Thessalonike receives special attention; it is argued that his refusal to surrender the city partially stemmed from his desire to save face. In the chapter, Manuel's Discourse to Thessalonians is analysed with regards to its political messages, literary features and reliance on Aristotelian ethics.

The chapter focuses on years 1387–91, covering Manuel's exile in Lesbos and Lemnos, and his subsequent return to Constantinople. Two of Manuel's works, the Discourse to Kabasilas and the Panegyric to John V, are analysed at length with regards to Manuel's self-representation, as well as their literary features and political messages. Manuel's daily life in Lemnos and his friendship with Kydones is discussed through their letters. The civil war between John V, John VII and Manuel is a prominent focus of the chapter, with e=special focus on Manuel's role in the events and how the episode influenced Manuel's later reign.

This chapter chiefly deals with Manuel's ethico-political works, his Foundations of Imperial Conduct and the Seven Ethico-Political Orations. They are analysed with regard to the emperor's ethico-political thought, his reliance on Aristotelian ethics, his self-representation and the political messages he embedded into these works. Manuel's literary network, manuscripts and his collaborations with the literati are further investigated, while panegyrics and other works addressed to the emperor receiveattention. In this regard, the emperor's reactions to praise and criticism are examined, offering an insight into his personality. The chapter ends with a discussion of the political situation between the years 1416–21 and an analysis of the political differences between Manuel and his son John VIII.