The chapter focuses on Manuel's travels in Western Europe (1399–1402). It discusses at length the political aspects of his presence at the English, French and Italian courts, offering new interpretations of the events. Other topics are Manuel's personal experiences in Europe, and his letters and interactions with prominent European figures of the time. Manuel's use of relics as diplomatic gifts receives further attention. The Procession of the Holy Spirit, a theological treatise penned by the emperor at time, is analysed at length with regard to its literary features, connections to the other treatises of time and Manuel's theological thought. Other shorter writings from the same period are also investigated. The chapter ends with the defeat of the Ottomans by Tamerlane and Manuel's subsequent return to Constantinople.

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 introduction sets forth the goals and the methodologies of the study. It reviews the previous scholarship on Manuel II Palaiologos and explains the contributions made by this book. While setting the scholarly background of the book, previous studies on Late Byzantine political and socio-economic history, Byzantine literature, Byzantine philosophy and theology are discussed in relation to Manuel's biography. By relying on studies on historical biography writing and some select examples from historical biographies of Western medieval rulers, the metholodology for writing Manuel's biography is established. The sources used in the biography are introduced and their chief characteristics are discussed.

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 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.

Dionysios Stathakopoulos’ chapter is divided in two parts. In the first he presents the textual sources that have had a seminal influence on the establishment of a visual vocabulary of transgressions that appear in depictions of Hell in monumental painting. He focuses on the development of ideas of punishment in the afterlife, tracing their origins from the Old and the New Testament and apocryphal texts to late Byzantine theology, which were popular in shaping ideas on punishment. Since, however, they do not always assist our understanding of the iconography of Hell, as this also reflects the social preoccupations of the community that commissioned the cycles, Stathakopoulos, in the second part of his chapter, turns to Joseph Bryennios (born around 1350), who recorded a vivid depiction of his experiences during his appointment on Crete, in an attempt to look into the contemporary society that commissioned the Cretan Hell cycles that lie at the heart of this publication.