The storm of Chalkis
It is 199 BC, and the war between the Romans and the Macedonians is raging. Informed by renegades, C. Claudius Cento, the consul for 200/199, based in Athens along with his fleet, hears that Chalkis, the key to Macedonia's operations, could be taken by surprise. He organizes a raid on the city with a flotilla and troops. Stealthily, he enters the city with a few men, opens a gate, and brings in most of his detachment. Violence flares. Houses near the agora are set ablaze. The fire spreads to the royal granaries and the arsenal. Massacres take place. The Acarnanian Sopater, commander of the garrison, is killed. The Rhodians who make up part of the Roman commando unit open the doors of the prisons where the Macedonians' political enemies are incarcerated. The statues of King Philip V are torn down or mutilated. Shortly afterward, the assailants return to their ships and leave for Athens. Rushing to the rescue, Philip V can only contemplate "the dreadful sight of an allied city half destroyed and still smoking" (Livy, XXXI 24, 3).
The sack of Eretria
A second military operation, broader in scope, occurred a year later. L. Quinctius Flamininus, the brother of the consul T. Quinctius Flamininus, at the head of a fleet of a hundred ships, including two Roman squadrons and the fleet of the kingdom of Pergamon, sailed to Eretria and besieged the city. "Eretria was then attacked with great ferocity, for the ships of the three combined fleets had brought with them all sorts of catapults and siege machines in order to destroy the cities, and the countryside provided an abundance of wood for constructing siege machines" (Livy, XXXII 16, 10). The defenders, exhausted and having many wounded, thought of surrendering, especially because the city wall was partly breached (Livy, XXXII 16, 11). But the Eretrians feared the Macedonian garrison as much as the Romans, and Philokles, the Macedonian commander in Chalkis, sent them encouragement and promised that help would soon arrive. Willingly or unwillingly, they continued to resist.
However, the Macedonian troops sent as reinforcements were penned up inside Chalkis by the Romans and their allies. The Eretrians then hastened to send representatives to King Attalos to ask his "indulgence and protection" (Livy, XXXII 16, 14). Considering this an offer to surrender and nursing the hope of an imminent peace treaty, "they placed guard posts only on the breached part of the wall, without worrying about the rest. Quinctius made his assault at night, using ladders to scale the walls on the side of the city where the Eretrians least anticipated an attack" (Livy, XXXII 16, 15). The city fell. "They found few coins and not much gold or silver, but the statues, paintings in an ancient style, and other ornamental objects of this kind were more numerous than one might have expected given the small number of the city's inhabitants and its other resources" (Livy, XXXII 16, 16-17). It is certain that the city was sacked, but nothing indicates that it was seriously damaged, since the intention was to liberate it from the Macedonian rule.