In the last decade of the 3rd century BC, the Romans became involved in Euboea for the first time, because of the war they were waging in Greece against King Philip V of Macedonia, then master of the island. At the beginning, only the city of Histiaea-Oreos (at the northern end of the island) was directly affected by the operations.
Somewhat later, in 199, the Roman legate G. Claudius Cento made a lightning attack on the center of Macedonian power in Euboea, Chalkis, although this attack had no immediate consequence.
The operations of 198 in Eretria
But the following year, in 198, the people of Eretria -like those of Karystos- became properly acquainted with the Roman armies. Arriving by sea with a large fleet, the Romans and their allies from Pergamon besieged the city, which was then still in the hands of a Macedonian garrison and which may have been hastily provided with new fortifications. Terrified by the spectacle of the siege machines, the civilian population had taken refuge on the acropolis and was trying to obtain an honorable surrender when the Romans succeeded in breaking into the city walls. This army of "liberation" did not seriously damage the public and private buildings of the urban center (despite what has sometimes been thought). But Livy, in a fairly detailed account of the event, based essentially on the lost testimony of the historian Polybios, reports that, lacking large sums of silver and gold, the victors found in the city "ancient" works of art of great value. The visit of the Romans certainly resulted in the partial loss of Eretria's rich cultural heritage. The military operations were conducted by L. Quinctius Flamininus, the brother of the consul of 198, who finally led negotiations in person, with a view to defining a new status for the city.
Eretria was not formally freed of Macedonian rule until 196, when T. Quinctius Flamininus solemnly proclaimed the independence of the Greeks during the Isthmian Games near Corinth. Even afterwards, the city was almost ceded to Rome's ally, the powerful king of Pergamon, but Flamininus used all his authority to oppose this.
Eventually, in 194, after having sent away all the Roman garrisons, Titus Flamininus created a federal state in Euboea, with Chalkis as its capital and Amarynthos as its religious center; the existence of this federal state is confirmed by inscriptions and coins. But in 192 the new Euboean Confederation seems already to have become embroiled in the turmoil resulting from the so-called "Antiochan War," when the Seleucid King Antiochos III invaded Greece with his allies the Aetolians, who were also enemies of Rome.
After many vicissitudes, Chalkis, despite its large pro-Roman faction, had to open its gates to the "liberating" king. The Eretrians, like the people of Karystos, were soon obliged, willingly or unwillingly, to follow suit. This suddenly put them at the center of a large-scale conflict in the Mediterranean, but it was settled rather quickly, to the advantage of the Romans. And thanks to the intervention of the former consul Flamininus, the Euboean cities, which might otherwise have feared severe reprisals for their behavior (in particular Chalkis, of course), were spared by the victor.
Social and political life
The history of Eretria in the 2nd century BC, though perhaps less brilliant than in the past, is interesting in more than one respect. First of all, we can observe that the city was able to reconstitute at least part of its resources: alone in Greece with Athens and Chalkis, Eretria was able to issue, ca. 180-170, silver coinage in the so-called "new style." However, honorific decrees found in various parts of Greece and Asia Minor show that toward the middle of the 2nd century the Eretrians had to appeal quite often to foreign judges -something the Athenians could never bring themselves to do- in order to settle legal disputes among citizens. This clearly shows that the Eretrians were prey to serious tensions, no doubt as a result of the heavy debts that many had incurred.