Nearly two thousand years before Black Beard, Captain Kidd, and Calico Jack sailed the high seas, bands of pirates dominated the known world, striking fear into the heart of Rome. In the second century BCE, the Seleucid dynasty began to fall, weakening its powerful navy. This power vacuum allowed a group of pirates from Cilicia, a region in modern-day Türkiye, to rampage through the Mediterranean Sea. Outlaws from across the world began to flood to Cilicia and other ports ruled by these pirates to join them, bolstering this immense pirate fleet. As the Roman Republic embarked on a campaign against King Mithrades VI in 88 BCE, the pirates were able to openly rule the Mediterranean with no nation to stop them.

The Cilician Pirates targeted slower grain ships, seizing their resources and capturing the crew. The pirates also often captured Roman nobles, ransoming them for enormous sums of money. An infamous example of this was when the Cilicians kidnapped a young Julius Caesar for the second time in 75 BCE. According to Plutarch, a prominent Greek historian, the pirates attempted to ransom Caesar for only 20 talents of silver, but Caesar found this ransom to be insulting and demanded that the ransom be increased to 50 talents. After the ransom was paid, Caesar promised his captors that he would find them and crucify them. Although the pirates believed he was kidding, Caesar delivered on his promise, assembling a fleet, destroying the pirate ships that captured him, and executing the same men who imprisoned him. Although Caesar got his vengeance, piracy remained a major problem for Rome.

In 68 BCE, pirates sacked Ostia, a vital Roman port, capturing two senators, setting many buildings on fire, and enraging the Roman aristocracy. Additionally, the grain supply of Rome was depleted as a result of the Cilicians, causing starvation. These factors caused Rome to appoint Pompey special powers in order to reclaim the Mediterranean Sea. Pompey slowly cornered the pirate fleet, destroying many of the ships. Although small bands of marauders still roamed the seas, the Mediterranean would not see another pirate fleet as strong as the Cilicians again.