Since OCR invites us to parachute right into the middle of Philippic 2, here is a quick orientation of where exactly in the text we are when we reach § 44: after his opening statement (§§ 1–2) and his rebuttal of Antony’s attack on him (§§ 3–41), Cicero spends the following two paragraphs inveighing against his adversary’s skills as a public speaker, with particular reference to Antony’s oratorical efforts in the period immediately after Caesar’s assassination. This transitional section (§§ 42–43) helps to set up the second main part of the speech, which begins here in § 44: it features a prolonged and systematic assault on Antony. This portion is of prodigious length (§§ 44–114) and will bring us right up to the concluding peroration (§§ 115–19). Still, Cicero alleges at the end of § 43 that in detailing Antony’s depravities he will proceed selectively, so as to have something in reserve for future jousts (nec enim omnia effundam, ut, si saepius decertandum sit, ut erit, semper novus veniam). Shortage of subject matter won’t be a problem: after all, Antony’s vices and misdeeds are legion (quam facultatem mihi multitudo istius vitiorum peccatorumque largitur).
One theme that offers continuity across §§ 40–44 is ‘inheritance and bankruptcy’. Cicero concludes his self-defence by debunking Antony’s slur that bequests do not come his way (§ 40: hereditates mihi negasti venire), before noting, at the beginning of § 42, that this line of attack is a bit rich coming from someone like Antony who refused to accept his father’s estate because it was loaded with debts (quamquam hoc maxime admiratus sum, mentionem te hereditatum ausum esse facere, cum ipse hereditatem patris non adisses). Antony senior died debt-ridden around 71 BCE, when Antony junior was eleven or twelve years old, and Cicero chooses this shameful loss of family fortune as the point of departure for his obloquy in § 44. It enables him to suggest that Antony comes from a disreputable branch of the gens Antonia and lacks filial pietas on top (since he chose to disown his father). And it dovetails nicely into his main line of attack in the opening paragraph, Antony’s shockingly disgraceful sex-life, including the willingness to earn money as a male prostitute before ending up as Curio’s toy-boy.