…Sicily was the first of all foreign nations to turn to the friendship and protection of the Roman people. She was the first of all to receive the title of province, the first such jewel in our imperial crown. She was the first who made our forefathers perceive how splendid a foreign empire is. No other people have equaled her loyal good will toward us …. For the great power of Carthage would never have been crushed so readily had not Sicily been at our disposal, supplying us with grain and affording safe harborage to our fleets.

Cicero, Second Speech Against Verres II. i. 2-iii.8

The Second Punic War had seen Syracuse allied to Carthage, and Rome sent four legions to place the city under siege. In 212 BC the city was assaulted while the defenders were somewhat incapacitated by overindulgence during a religious festival, and Rome gained control of the entire island. It was during this assault that the inventor Archimedes, who had helped in the defense of the city, was killed despite orders from the Roman general Marcus Claudius Marcellus that he was not to be harmed. Marcellus is said by Plutarch (but not Polybius, who wrote a century earlier) to have spared the lives of the inhabitants, but carried off their art treasures to Rome.

The legal rights of the Sicilians are as follows. Cases between two citizens of the same city are tried in that city's courts under that city's laws. For cases between two Sicilians of different cities, the praetor chooses jurors by lot… When an individual sues a community or a community an individual, the council of some city is named to try the case, each party being entitled to one challenge. When a Roman citizen sues a Sicilian, a Sicilian is appointed to try the case, and when a Sicilian sues a Roman citizen, a Roman citizen is appointed. In all other cases the regular procedure is to nominate the jurors from a panel of Roman citizens resident in the district[.]

Cicero, Ibid.

Verres was accused of numerous offenses involving bribery and extortion, as well as the accusation that he had sentenced a Roman citizen be flogged and crucified – a very serious offense if true for a Roman citizen could receive neither punishment lawfully. Exactly how corrupt Verres really was is difficult to determine as all the surviving information is provided by Cicero, who prosecuted the case when it was brought to trial in 70 BC. No sentence was ever delivered in the case because after Cicero gave his first oration Verres fled in voluntary exile to Massilia, where he was eventually proscribed by Marcus Antonius in a dispute over statuary. The subsequent orations were never delivered but were assembled and published by Cicero.

Cicero's Second Speech Against Verres also provides illumination on the tax structure of the Roman province of Sicily.

Two cities, Messana and Tauromenium, have special treaties of alliance and no contracts are made for collecting tithes from them five others, though not allies by treaty, are free states exempt from taxation, namely, Centuripa, Halaesus, Segusta, Halicyae, Panhormus. With these exceptions, all the lands of the Sicilian cities are subject to payment of tithe, and were so under regulations voluntarily made by their own inhabitants before the days of Roman sovereignty… It was Verres' duty to make purchases of grain in Sicily in accordance with a decree of the senate and the provisions of the Terentian-Cassian grain law [passed 73 BC]. There were two kinds of purchase to be made, the first a tithe, the second an additional purchase distributed fairly among the communities.

Cicero, Second Speech Against Verres III. V. I-VI. 15, lxx, 163.

Sicily was a valuable source of grain to Rome, as the island paid an annual tithe of three million modii of wheat, with a single modius being roughly equivalent to a peck. Although Rome's influence was not imposed in the cities with any great force, and thus the culture of Sicily remained substantially Greek, the importance of Sicilian grain meant that many Romans owned extensive latifundia in the countryside. These great estates were worked by harsh slave labor, and slave rebellions were a constant concern. The slaves were so ill-fed they often resorted to robbery, and since the large absentee landlords were happy so long as they didn't need to pay for their slaves' food, the situation continued. On two occasions serious uprisings occurred. The First Servile War occurred between 135-132 BC, led by a man named Eunus. Said to be a Syrian from Apamea, he had apparently been a prophet and conjurer before the revolt. With the assistance of a Cilician lieutenant named Cleon they probably led close to two hundred thousand rebel slaves (including women and children) at the height of the rebellion. A second revolt occurred approximately thirty years later, between 104-103 BC, led by two slaves named Tryphon and Athenion. This Second Servile War was crushed by the Roman Consul Marcus Aquilius only with great difficulty.

The large number of slaves, and the constant risk of revolt, was why the gladiator Spartacus sought to travel from Italy to Sicily, as the island was a very likely source of recruits. However Spartacus was betrayed by the pirates he sought to hire for transport and thus never reached Sicily.

War returned to Sicily with the Civil War between Julius Caesar and Gnaeus Pompeius. Pompey's son Sextus Pompey managed to escape to Sicily in 45 BC after the defeat at the Battle of Munda in which his brother Gnaeus had been killed. The assassination of Caesar on the Ides of March gave Sextus time to prepare and he was able to hold off the Second Triumvirate for several years, until 39 BC when Sextus and the triumvirs signed the Pact of Misenum. An armistice on the Sicilian front became useful to the triumvirate because they wanted as many legions as possible for Marcus Antonius' anticipated campaign against Parthia. The ceasefire did not last long. Octavian tried to conquer the island only to have his navy defeated off Messina in 37 BC and again in August of 36 BC. But by that time Octavian had appointed Marcus Vipsanius Agrippa as his commander, and a month later Agrippa destroyed Sextus' navy off Cape Naulochus. Sextus lost his base of operations and escaped to the east, where he was caught in Miletus in 35 BC and executed without trial by Marcus Titius, one of Octavian's subordinates.