Cover photo: “The capture o Miletus” by Andre Castaigne. After seizing Miletus, Alexander the Great headed to Halicarnassus.

Once Alexander settled his matters, after the great victory at the battle of Granicus, the Macedonian king proceeded towards Caria, as he had been informed that significant Persian and mercenary forces had gathered in Halicarnassus. Consequently, along his route, he seized by assault any cities situated between Miletus and Halicarnassus and established his camp near Halicarnassus itself, about a kilometre (5 stadia, about 900 meters) distant from the city, believing that its siege would last a long time.

The natural fortifications of Halicarnassus rendered it a formidable natural stronghold surrounded by a moat some 13m deep and 7m wide. Its apparent vulnerabilities had long been fortified under the personal direction of Memnon the Rhodian, a formidable and dangerous enemy, appointed by Darius as general of Lower Asia and commander of the entire navy. The city harbored numerous foreign mercenaries and Persian troops, while its port bustled with warships, their crews poised to bolster its defenses.

On the initial day, as Alexander led his forces toward the city walls, the besieged attempted a sortie, resulting in a brief skirmish swiftly quelled by Alexander’s troops. Several days later, Alexander embarked on a reconnaissance mission, accompanied by his elite guards, cavalry, and infantry regiments, along with archers and Agrianian (light infantry, mostly peltasts) scouts. They scoured the city’s perimeter facing Myndus (1), assessing potential vulnerabilities and exploring the feasibility of a clandestine night raid to secure Myndus’ cooperation—a strategic move he believed would greatly enhance the Halicarnassian siege.

Certain Myndians had made a solemn promise to surrender their city to Alexander under the cloak of darkness. True to their word, he approached the city walls at the stroke of midnight. However, to his dismay, there was no sign of cooperation from the Myndian populace, nor had he brought along siege engines and ladders, for his intent was not outright conquest but rather a stealthy takeover of Myndus. Nonetheless, he positioned his Macedonian phalanx close to the city and instructed them to undermine the walls. Although the Macedonians managed to topple at least one tower, the breach was not sufficient to penetrate the defenses.

Facing stout resistance from the defiant Myndian defenders and bolstered by reinforcements from Halicarnassus, Alexander realized that seizing Myndus without adequate preparation and the element of surprise was a daunting task. Thus, he opted to retreat without achieving his intended goals, redirecting his attention once more to the ongoing siege of Halicarnassus.

To begin with, he initiated the filling of the trench dug by the besieged defenders just outside their city walls with earth. This strategic move aimed to clear the way for the advancing mobile towers, which he planned to deploy to launch projectiles against the defenders and their fortifications. The trench was swiftly filled, allowing the mobile towers to be maneuvered closer to the walls.

Under the cloak of darkness, the defenders of Halicarnassus launched a daring night sortie, intent on setting fire to the approaching mobile towers and other siege machinery already positioned or ready to be deployed along the walls. However, their efforts were thwarted by the swift response of the Macedonian guards and other soldiers, who managed to repel the attackers and secure the machinery once more within the confines of the city walls.

The clash resulted in approximately one hundred and seventy casualties among the defenders of Halicarnassus. On the Macedonian side, around sixteen soldiers lost their lives, with approximately three hundred sustaining injuries, highlighting the challenges faced during nocturnal engagements. Τhen an unexpected event happened that almost caused the fall of the city.

The incident with the drunken soldiers who almost caused the fall of the city

After a brief period, two Macedonian infantrymen belonging to Perdiccas’ unit found themselves sharing a tent, enjoying a few cups of wine. As the alcohol flowed and their spirits rose, they began boasting about their individual exploits. As their conversation turned more heated, perhaps fueled by the wine, they suddenly seized their weapons and launched an impromptu attack on the walls (!). It seemed more like a display of bravado than a strategic move against the enemy.

However, some keen-eyed Halicarnassians noticed the two soldiers approaching the walls recklessly and promptly rushed out to confront them. Despite being outnumbered and in a vulnerable position, the Macedonians fought off those who came too close and began firing arrows at those further away, as the enemy attempted to storm the walls and rain down arrows from above.

In the meantime, more soldiers from Perdiccas’ unit and other defenders from Halicarnassus joined the fray, resulting in a fierce skirmish near the walls. The Macedonians managed to seal the gates again, trapping those who had ventured out. The city was nearly on the brink of being overrun, as the walls were momentarily less guarded, and two towers had collapsed, along with a portion of the wall between them! Had all of Alexander’s soldiers actively participated, breaching the wall would have been a distinct possibility. Moreover, the third tower was already weakened, and demolishing it would have been feasible if the Macedonians had dug beneath it. However, the besieged swiftly reconstructed the fallen section of the wall using bricks in a crescent shape, thanks to the abundance of laborers at their disposal.

Contiunance of the siege

The siege dragged on for several weeks, marked by a series of unsuccessful sorties from the besieged, resulting in bloody clashes, particularly for the attackers. The following day, Alexander advanced his siege machinery against the city walls. Despite the inhabitants’ repeated attempts to repel the assault and set fire to the siege engines, only partial success was achieved. Some of the protective barriers surrounding the wall and a portion of a wooden tower were indeed engulfed in flames, but the majority were saved by the vigilant defense efforts of Philotas and Elanicus, to whom the city’s safety had been entrusted. However, when Alexander’s forces appeared during the sortie, the besieged populace hastily abandoned their torches and weapons, seeking refuge behind the safety of their fortified walls.

A few days later, Alexander led his siege engines against the inner brick wall while supervising the operation personally. A general sortie was launched from the city, catching the Macedonians off guard. The defenders hurled burning torches and other materials at the Macedonian engines, but fierce counterattacks from Alexander’s soldiers quickly drove them into retreat. Significant casualties occurred, with some falling in clashes with the Macedonians and others perishing around the demolished wall due to the narrow passage and piled rubble hindering their escape. A significant slaughter occurred at this juncture, as more individuals participated in the sortie, displaying greater boldness. Some were killed in clashes with the Macedonians, while others perished around the demolished wall due to the narrow passage being insufficient for such a large crowd. The piled rubble of the wall further impeded their passage.

Last days of resistance and fall

Once again, the defenders attacked from the gate of Tripylum encountered Ptolemy, the royal bodyguard, and his formidable troops. With effortless precision, they repelled the city’s sortie, forcing the besieged to retreat. However, their escape turned into tragedy as they became ensnared on a narrow bridge spanning a moat, which buckled under their weight, claiming many lives. Macedonian soldiers, seizing the advantage, rained down deadly blows from above.

Yet, the most devastating loss unfolded at the city gates. Closed prematurely in a panicked frenzy, they inadvertently sealed the fate of their own comrades, who met their demise at the hands of the Macedonians just outside their walls. This grim turn of events teetered Halicarnassus on the brink of collapse, saved only by Alexander’s strategic withdrawal. Around a thousand besieged perished, while approximately forty of Alexander’s soldiers fell, among them Ptolemy, Clearchus, leader of the archers, and Adaeus, the chiliarch, alongside other distinguished Macedonians.

Consequently, the Persian commanders Orontobates and Memnon convened and concluded that, given the circumstances, they could not withstand the siege for much longer. They withdrew from the city and took refuge in its fortified citadel. Alexander surveyed the heights occupied by the Persians and mercenaries and decided against besieging them. He realized that such an endeavor would significantly delay him due to the natural fortifications of the terrain. Moreover, capturing those positions held little strategic importance, as he already controlled the entire city and soon the citadel also fell to the Greek hands.

(1)City ​​of Caria, in Asia Minor, built on the peninsula of Halicarnassus.

Sources/ Bibliography

Arrianus, The Anabasis of Alexander

S. English, The sieges of Alexander the Great, publ. Pen and Sword Military, 2009.

I. Worthington, By the Spear: Philip II, Alexander the Great, and the Rise and Fall of the Macedonian Empire, publ. Oxford University Press, 2016.