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 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 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.