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 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.