Two descriptions of the siege survive and they match each other most interestingly; the one, written by Alexander's officers, again minimizes his difficulties, confirmation of the way in which the myth of his invincibility was later developed by contemporaries; the other, probably based on soldiers' reminiscences and Callisthenes's published flatteries, rightly stresses the city's resistance and notes that the defenders were led by two Athenian generals with the stirringly democratic names of Thrasybulus and Ephialtes, whose surrender Alexander had demanded in the previous autumn; though spared, they had crossed to Asia to resist the man who was supposed to be avenging their city's past injustices. A third leader, it was agreed, was a Macedonian deserter, probably the son of one of the Lyncestians who had been killed at the accession; they made a strong team, but neither of the histories makes it plain that their main defence was to last for two months, including the heat of August.
At first, Alexander skirmished lightly, probably because his siege engines had not yet laboured their slow way by road from the harbour some six miles to the rear, the one port unoccupied by the Persians' fleet. He encamped on level ground half a mile from the north-east sector of the wall and busied his men first with an unsuccessful night attempt to capture a sea-port some twelve miles west of the city which had falsely offered surrender, then with the filling of the ditch, 45 feet wide and 22 feet deep, which had made the north-east wall of Halicarnassus inaccessible to his wheeled siege towers. Diggers and fillers were sheltered by makeshift sheds until their ditch was levelled out and the siege-towers, newly arrived by road, could roll across it into position; thereupon catapults cleared the defenders, rams were lowered from the siege towers on to the walls, and soon two buttresses and an appreciable length of fortifications had been flattened. Undaunted, the defence sallied forth by night, led by the renegade Lyncestian; torches were hurled into the wooden siege engines and the Macedonian guards were unpleasantly surprised in the darkness before they had time to put on their body-armour. Having made their point, the defenders retired to repair the hole in their outer wall and build a semi-circular blockade of brick on hilly ground. They also finished a sky-high tower of their own which bristled with arrow-catapults.
The next incident is unanimously ascribed to the heartening effect of drink. One night, two or more soldiers in Perdiccas's battalion, flown with insolence and wine, urged on their fellows to a show of strength against the new semi-circular wall. The ground was unfavourable, the defenders alert and amid a flurry of catapults, Memnon led such a counterattack that Alexander himself was forced to the rescue of his disorderly regiment. But though the defenders retired, they did so as they pleased: Alexander had to admit defeat and ask for the return of the Macedonian dead, the accepted sign that a battle had been lost. In his history, King Ptolemy recorded the start of this drunken sortie, knowing that it discredited Perdiccas, the rival with whom he had fought after Alexander's death, but he suppressed the defeat which followed, unwilling to reveal a failure by his friend Alexander; it thus went unsaid that within the city, the Athenian exile Ephialtes had urged his fellow defenders not to return the enemy bodies, so fervent was his hatred of the Macedonians.
Anxious at this setback, Alexander battered and catapulted as furiously as ever. Again the Persians sallied, and again, covered by their fellows from higher ground, they came off well. That was only a prelude. A few days later, they planned their most cunning sortie, dividing themselves into three separate waves at Ephialtes's bidding. The first wave was to hurl torches into Alexander's siege-towers in the north-east sector; the second was to race out from a more westerly gate and take the Macedonian guards in the flank, while the third was to wait in reserve with Memnon and overwhelm the battle when a suitable number of opponents had been lured forward. According to the officers, these sorties were repelled 'without difficulty' at the west and north-east gates; in fact, the first two waves did their job splendidly and Alexander himself was compelled to bear the brunt of their onslaught. The entry of the third wave into the battle startled even Alexander, and only a famous shield-to-shield rally by a battalion of Philip's most experienced veterans prevented the younger Macedonians from flinching and heading for camp. However, Ephialtes was killed, fighting gloriously at the head of his hired Greeks, and because the defenders shut their gates prematurely, many of his men were trapped outside at the mercy of the Macedonians. 'The city came near to capture,' wrote the officers, 'had not Alexander recalled his army, still wishing to save Halicarnassus if its citizens would show a gesture of friendliness.' Night had fallen and presumably Alexander's men were in some disorder; if he had thought he could attack successfully, citizens or no citizens, as at Miletus, he would have done so.
That night the Persian leaders decided to abandon the outer city: the wall was broken, Ephialtes was dead, their losses were heavy and now that their garrison had dwindled, perhaps they feared betrayal by a party within the city. 'In the second watch of the night', about ten o'clock, they set fire to their siege-tower, their arsenals and all houses near to the walls, leaving the wind to do its worst. The satrap Orontobates decided to hold the two promontories at the entrance to the harbour, trusting in their walls and his mastery of the sea.
When the news reached Alexander's camp, he hurried into the city, giving orders, said his officers, that any incendiaries should be killed, but that Halicarnassian citizens in their homes should be spared. When dawn showed him the extent of the damage, he 'razed the city to the ground', a detail recorded in both versions but evidently exaggerated as the city's famous monuments remained unscathed. Probably, Alexander only cleared a space from which to besiege Orontobates's two remaining strongholds, for some 3,000 troops were ordered to continue the siege and garrison the city. As Halicarnassus had been stubborn, there was no reason to give her a democracy or call her free. She was a Greek city, but she was not Ionian or Aeolian and had been promised nothing; her promontories were to hold out for another whole year and serve the Persian fleet as a base of supply. But Caria, at least, had fallen; mother Ada was named its satrap and given troops under a Macedonian commander to do any work
that might prove too strenuous for an elderly woman. Thus, under a female eye, Alexander's principle of a province split between a native satrap and a Macedonian general was introduced for the first time.
The siege of Halicarnassus leaves a mixed impression. Alexander had persevered, and personally he had fought with his usual courage, but his victory, and that only within its limits, was not due to bold ingenuity or mechanical subtlety so much as to outnumbering an enemy who had sallied repeatedly. None the less, an important point of supply for an Aegean fleet had been breached, if not wholly broken, and as autumn was far advanced, most generals could have been forgiven for relaxing. Typically, Alexander did nothing of the sort.
Before advancing, he gave orders that all Macedonians who had married 'shortly before his Asian campaign' should be sent back home to Macedonia to spend the coming winter with their wives. 'Of all his actions, this earned Alexander popularity amongst his Macedonians', besides helping their homeland's birthrate and encouraging more reinforcements. Led by the husband of one of Parmenion's daughters, the bridegrooms bustled homewards, and Alexander thinned out his forces, detailing Parmenion to take the supply wagons, the Greek allies and two squadrons of cavalry back by road to Sardis and thence to await him further east on the Royal Road. The siege equipment was despatched to Tralles, and ever inexhaustible, Alexander announced that he would head south to the coast of Lycia and Pamphylia 'to hold the seaboard and render the enemy useless'.