Thebes knew better than most what rebellion against Macedon could cost. Alexander the Great had razed it to the ground a generation earlier, and the city standing here in 292 BC was a reconstruction, rebuilt by Cassander only years before. Yet in 293 the Boeotians rose against Demetrius and were swiftly put down. The next year they rose again, led once more by Peisis of Thespiae, the very man Demetrius had pardoned the first time. Mercy had not bought loyalty. This time the king brought his siege train to settle the matter.

Demetrius did not earn his epithet by accident. To the walls of Thebes he hauled the Helepolis, the "Taker of Cities," a siege tower so famous it was a legend in its own time: a moving fortress of timber and iron, storeyed and armored, designed to overtop any rampart and pour fire and stone onto the defenders within. It was the most advanced war machine of the Hellenistic age. And yet, against the stubbornness of the Thebans, even the Taker of Cities faltered. The walls held. The assault crawled. The machine that had broken other cities met one that would not break on schedule.

Mid-siege, the wider chessboard of the successor kingdoms intruded. Word reached Demetrius that Lysimachus, a rival diadoch, had been captured by the Getae of the lower Danube, and Demetrius broke off to march for Thrace, hoping to seize a suddenly undefended kingdom. He left his son Antigonus to command the siege in his absence. The opportunity dissolved when Lysimachus was released, and Demetrius returned to Boeotia to finish what he had started. The Thebans, in the meantime, had not yielded an inch of their walls.

What followed was a grinding, bloody patience. Demetrius drove his men forward again and again at terrible cost, even when there was little prospect of breaking through, and it was this that drew his son's anguished question and the king's icy reply. But Demetrius spent his own life as recklessly as his soldiers': at Thebes he was badly wounded, struck through the neck by a bolt. He survived. So, for a while longer, did the city's resistance, until at last the walls gave and Thebes fell, in 291 BC by most reckonings, perhaps as late as 290.

Then came the surprise. The king who had squandered armies to take the city chose not to make it pay in blood. Demetrius showed leniency, executing only a handful of the rebellion's ringleaders and sparing the population. Whether the wounded conqueror had exhausted his appetite for slaughter, or simply judged a living Thebes more useful than a dead one, the sources do not say. Twice-rebuilt and twice in revolt, the ancient city endured. Today the modern town of Thebes rises over those contested foundations in the Boeotian plain, where one of antiquity's most relentless besiegers met a wall he could not quickly break.