This was the sequence of events described by the prosecution and the commentary of Asconius, an ancient world commentator who analyzed several of Cicero's speeches and had access to various ancient documents which are no longer extant. The absence of a summary of the chain of events in Cicero’s speech may be attributed to their incriminating evidence against Milo. Presumably, Cicero realized that this was the primary weakness, and as the trial unfolded it turned out to be so. We can assume from the fact that the jury did indeed convict Milo, that they felt that although Milo may not have been aware of Clodius's initial injury, his ordering of Clodius’s butchering warranted punishment.
When initially questioned about the circumstances of Clodius’s death, Milo responded with the excuse of self-defense, that it was Clodius who laid a trap for Milo in which he might kill him. Cicero had to fashion his speech to be congruent with Milo's initial excuse, restraint which probably affected the overall presentation of his case. In order to convince the jury of Milo’s innocence, Cicero used the fact that following Clodius's death, a mob of his own supporters, led by the scribe Sextus Cloelius, carried his corpse into the Senate house (curia) and cremated it using the benches, platforms, tables and scribes' notebooks as a pyre. In doing so they also burnt down much of the curia; the Clodian supporters in their fury also launched an attack on the house of the then interrex, Marcus Lepidus; and therefore Pompey ordered a special inquest to investigate this as well as the murder of Clodius. Cicero refers to this incident throughout the Pro Milone, implying that there was greater general indignation and uproar at the burning of the curia than there was at the murder of Clodius.
Due to the violent nature of the crime as well as its revolutionary repercussions (the case had special resonance with the Roman people as a symbol of the clash between the populares and the optimates), the special inquest set up by Pompey included a hand-picked panel of judges. This was in order to avoid the corruption that was rife in the political scene of the late Roman Republic). In addition, armed guards were stationed around the law courts to placate the violent mobs of each side's supporters.
The first four days of Milo’s trial were dedicated to opposition argument and the testimony of witnesses. On the first day Gaius Causinius Schola appeared as a witness against Milo and described the deed in such a way as to portray Milo as a cold-blooded murderer. This worked up the Clodian crowd who in turn terrified the advocate on Milo's side, Marcus Marcellus. As he began his questioning of the witnesses, the Clodian crowd drowned out his voice and surrounded him. This action taken by Pompey prevented too much furore from the vehemently anti-Milonian crowds for the rest of the case. On the second day of the trial the armed cohorts were introduced by Pompey. On the 5th and final day, Cicero delivered the Pro Milone in the hope of reversing the damning evidence accrued over the previous days.
Clodius is made out repeatedly in the Pro Milone to be a malevolent, invidious, effeminate character; craving power and organizing the ambush on Milo. In his speech Cicero gives Clodius a motive for setting a trap: his realization that Milo would easily secure the consulship, and thus stand in the way of Clodius' scheme to attain greater power and influence as a praetor. Fortunately, there was plentiful material for Cicero to build this profile, such as the Bona Dea incident in 62BC; involving Clodius stealing into the abode of the Pontifex Maximus of the time, Julius Caesar, during the ritual festival of the Bona Dea, to which only women were allowed. It is said that he dressed up as a woman in order to gain access and pursue an illicit affair with Pompeia, the wife of Caesar. Clodius was taken to the law courts for this act of great impiety, but escaped the punishment of death by bribing the judges, most of whom had been poor (according to Cicero, who was the prosecutor during the case). Earlier in his career Lucullus had accused Clodius of committing incest with his sister, then Lucullus's wife; this too is often referred to in order to blacken Clodius's reputation.
Milo, on the other hand, is perpetually depicted as a 'saviour of Rome' by his virtuous actions and political career up until that point. Cicero even goes as far as to paint an amicable relationship with Pompey. Asconius, as he does with many other parts of the Pro Milone, disputes this fact, claiming that Pompey was in fact afraid of Milo, "or else pretended to be afraid", staying in the upper parts of his property in the suburbs and employing a constant body of troops to keep guard. His fear was attributed to a series of public assemblies in which Titus Munatius Plancus, a fervent supporter of Clodius, stirred up the crowd against Milo and Cicero, casting suspicion upon Milo by shouting that he was preparing a force to destroy him. However, in the view of Plutarch, a first century AD writer and biographer of notable Roman men, Clodius had also stirred up enmity between Pompey and himself, along with the fickle crowds of the forum he controlled with his malevolent goading.
The early part of the refutation of the opposition's arguments (refutatio), contains the first known exposition of the phrase silent enim leges inter arma ("in times of war, the laws fall silent"). This has since been rephrased as inter arma enim silent leges . At this point in the speech this phrase is integral to Cicero's argument. In the context of the Pro Milone the meaning behind the phrase remains the same as its use in contemporary society. Cicero was asserting that the killing of Clodius was admissible so long as it was an act of self-defence; postulating that in extreme cases, where one's own life is immediately threatened, violence without proper regard to the laws is justifiable. Indeed, Cicero goes as far as to say that such behaviour is instinctive (nata lex: "an inborn law") to all living creatures (non instituti, sed imbuti sumus: "we are not taught [self-defence] through instruction, but through natural intuition". This argument of the murder of Clodius being in the public interest is only presented in the written version of Pro Milone, as, according to Asconius, Cicero did not mention it in the actual version delivered).
The Pro Milone which survives to date is a rewritten version published by Cicero after the trial. Despite its failure to secure an acquittal, the surviving rewrite is considered to be one of Cicero's best works: thought by many to be the magnum opus of his rhetorical repertoire. Asconius describes the Pro Milone as "so perfectly written that it can rightly be considered his best".
The speech is full of deceptively straightforward strategies. Throughout his speech Cicero explicitly seems to follow his own rhetorical guidelines published in his earlier work De Inventione, but on occasion subtly breaks away from these stylistic norms in order to emphasise certain elements of his case and use the circumstances to his advantage. As example, he places his refutation of the opposition's arguments (refutatio) far earlier in the speech than expected, and pounces on the opportunity to disprove quickly the plethora of evidence collected over the first four days of the trial). His arguments are interwoven with one another and coalesce during the conclusion (peroratio). There is heavy use of pathos throughout the speech, starting with his assertion of fear for the guards posted around the courts by Pompey in this special inquisition (the very first word of the speech is vereor - "I fear"). However, Cicero ends his speech fearless, becoming more emotive with each argument, and finally finishing by the beseeching of his audience with tears to acquit Milo. Irony is omnipresent in the speech, along with continual appearances of humour and constant appeals to traditional Roman virtues and prejudices, all of these tactics designed solely to involve and persuade his jury.
In many ways the circumstances surrounding the case were apposite for Cicero, forcing him back to his own oratorical foundations. The charge of vis ('violence') against Milo not only suited a logical and analytical legal framework with evidence indicating a specific time, date, place and cast for the murder itself, but generally concerned actions that affected the community. This allowed Cicero ample maneuvering room to include details of the fire in the curia, as well as the attack on Marcus Lepidus' house and the Bona Dea incident.
Milo, having read the later published speech whilst in exile, humorously commented that if Cicero had only spoken that well in court, he would "not now be enjoying the delicious red mullet of Massilia".