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 Manuel's childhood and adolescence. His education, upbringing, relations with family and relatives, and childhood memories are discussed through his own writings and other sources. The inital relationship between Manuel and his teacher Demetrios Kydones is traced. The political, socio-economic and cultural background for Manuel's reign is set. The chapter concludes with Manuel's voyage to Buda in 1369 and his later literary representation of the episode.

The chapter covers the blockade of Constantinople, 1394–1402. Topics discussed include Late Byzantine Constantinople, the socio-economic conditions during the siege of 1394–1402 and Manuel's political acts, his negotiations with Venice and his role in the Crusade of Nikopolis receive special attention. In the domestic spehere, Manuel's role in the anti-Palamite purges of 1369 and his stance towards Palamism is discussed at length. A little known work by Manuel, the Discourse to Iagoup, is analysed in light of Manuel's aversion to criticism, his views on Palamism, Orthodox and Catholic theology and the relationship between philosophy and theology. Once more, his self-representation and the political messages in the work, are taken into account. His Dialogue on Marriage is also analysed, focusing on its literary features, the representation of Manuel and John VII, and its political messages. Through the Dialogue and other works, Manuel's views on marriage are discussed. Finally, the chapter investigates Manuel's diplomatic relations with the West and his decision to travel to Europe to seek help.

The chapter focuses on Manuel's early reign, 1391–94. Manuel's participation in the Ottoman campaign is discussed at length, focusing on his relationship with Bayezid I and on the literary, political and autobiographical features of his letters from the campaign. His anti-Islamic work, the Dialogue with a Persian is analysed at length with regard to its theological content, literary features and Manuel's representations of himself and the Ottomans. Manuel's marriage to Helena Dragas, his relations with his nephew and rival John VII, the birth of the future John VIII are other topics that are covered. His governing style, political strategies and preoccupation with finances is extensively discussed through exploration of Manuel's official documents and Venetian Senate resolutions. The chapter ends with Manuel and Bayezid's clash in Serres in 1394, the commencement of the blockade of Constantinople and his later narration of these events.

The chapter focuses on the years 1369-82. The topics discussed are the civil war between John V, Andronikos and Manuel, Manuel's despotate in Thessalonike and his first trip to Venice. The discussions pay special attention to Manuel's representation of the events in his works, his relationship with his father and brothers and the emergence of his governing style. The political and economic policies of John V and Manuel are compared. It is argued that through his writings, Manuel represents an idealized version of his reign and life, omitting unpleasant or shameful episodes. Through the analysis of a chyrsobull of John V dated to 1371, it is argued that prior to 1374, John V had no intention of making Manuel his heir.

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.

The final chapter of the book discusses the last years of Manuel's life. The chief topics of discussions are his advanced age and its representation in the sources, his illness and his final struggles with the Ottomans. A section of the chapter offers a final evolution of Manuel's reign and its outcomes. The emperor's four sermons and confessional works are analysed with regard to their literary style, Manuel's self-representation and his theological thought. The chapter concludes with Manuel's death and a discussion of his legacy.

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.