This commentary offers the reader a set of letters (or letter parts) written by Cicero, Paul, and Seneca, which have been selected against the Transformational Leadership categories of idealised influence, inspirational motivation, intellectual stimulation, and individualised consideration. Chapter 1 offers introduction into authors and theory: all three letter writers are considered as ancient leadership figures composing leadership letters. The letters selected are presented in original text facing a translation (Chapter 2). Chapter 3 provides analysis and discussion of each letter, and aims to introduce the reader to the historical and literary contexts before reading the letter through the lenses of Transformational Leadership theory. Chapter 4 sums up the findings on each letter and each letter writer in light of Transformational Leadership and its categories. The volume is aimed at all those who are studying the function of ancient letter-writing - especially the letters of Cicero, Paul, or Seneca.