This chapter examines Ep. 2.20’s intertextual engagement with Demosthenes’ De Corona and Cicero’s In Verrem. By analysing these ‘allusions’, we can determine that Pliny self-identifies with his famous oratorical predecessors. More specifically, Pliny’s feud with Regulus recalls Demosthenes’ rivalry with Aeschines and Cicero’s oratorical competition with Verres. Pliny casts himself as a successor of this tradition and, like his great forebears, can overcome his nemesis. Yet the letter also has a more poignant political point about Pliny’s civitas (community). Demosthenes claims that some individuals who were involved in Greek political affairs were bribed by Philip. Aeschines was therefore symptomatic of a wider failing among the Greek political elite. Similarly, Cicero claims that high ranking senators support men such as Hortensius so long as it benefits their own careers. By bringing Cicero and Demosthenes to mind, then, Pliny suggests that his own political elite community reward wicked men such as Regulus in much the same way. In fact, Pliny’s letter seems to suggest an even gloomier future, where his own civitas are worse than the precedent of the past. These intertextual allusions, then, can challenge common scholarly pre-conceptions about Pliny’s view of Rome’s future under the Trajanic principate.