This article is a study of Valerius Maximus’ understanding and rewriting of late republican history through his portrayal of Gnaeus Pompeius Magnus in chapter 6.2 of the Facta et dicta memorabilia. In chapter 6.2, ‘on the freely spoken and freely done’, Pompeius is mentioned in six consecutive exempla as the addressee of public criticism in episodes set between the 60s and 51 b.c. By offering a close reading of this chapter and by investigating its organizational criteria and themes, particularly Pompeius’ power, his silence and libertas, this article argues that Valerius aims to display how crucial the years of the ‘first triumvirate’ were in the development towards an inevitable autocracy. It suggests, moreover, that Valerius envisions the Facta et dicta as a work closer to historiography than usually appreciated.