With the death of Darius, the Macedonians thought the war was over. The remote territories had little to offer economically. As the Iranians had been reluctant to acknowledge a ruler of their own race, they could be expected to be even more resistant to Alexander's conquest, so that large garrisons would be required to maintain power. Alexander, however, wanted to continue pressing east, using Bessus as an excuse. Bessus was still out stirring trouble, as he attempted to raise an army to defend the old empire. However, discord arose among his own faction, and soon Bessus was ousted by Spitamenes, who gladly surrendered him to Alexander. Bessus was forced to wear a wooden collar, the mark of a slave, while Spitamenes was praised by Alexander. Bessus would later be mutilated, having his nose and ears cut off before being executed.
The capture of Bessus, however, did not mean the end of the revolt as Alexander had thought. Instead, the leaders of Sogdiana had hoped that turning Bessus over would gain them immunity; when it became evident that Alexander still intended to subjugate their territory, they rose once again. When Alexander continued on, Spitamenes raised troops who slaughtered the Macedonian garrisons. Alexander was therefore forced to return to the city of Cyropolis, the center of the revolt. As he usually dealt with cities that refused to submit, he razed and massacred Cyropolis.
In the meantime, Spitamenes continued to stir trouble in other areas, so Alexander sent a small troop, led by Pharnuches, to take care of the situation. Pharnuches underestimated Spitamenes considerably. Spitamenes successfully lured Pharnuches to another territory where Spitamenes obtained further support, leaving the Macedonians surrounded. It is reported that not a single Macedonian escaped death in what was perhaps the first–and only–major defeat of Alexander's career. Though the blame falls largely on Pharnuches and his ineptitude, Alexander himself failed to appreciate the strength of Spitamenes' force, and his error in calculation was the ultimate cause of this defeat.
Spitamenes fled with his troops when Alexander's army made for their direction, but the fact remained that Spitamenes controlled most of Sogdiana. Alexander appointed Coenus, one of his generals, to supervise the rebel's activity while the Macedonians rested for the winter of 328 B.C. As Alexander and Coenus were secured more cities, Spitamenes was left without bases and means of provisioning. He therefore decided to round his troops up to make one great assault. Unfortunately for Spitamenes, Coenus was well prepared and defeated the rebels soundly. The Sogdianians deserted Spitamenes, and he was beheaded. Nevertheless, he is often remembered as Alexander's most formidable opponent, having won a major victory over the Macedonians and having harassed them for over two years–though in a full battle he never could have defeated them.
With the Sogdianian region taken care of, Alexander moved south to Paraetacene, which was still under the control of four powerful barons. The first of these, Oxyartes, had established a stronghold at the top of a steep mountain, and he was fully confident of its impenetrability. Alexander chose 300 of his best rock-climbers to undertake the mission, with the promise of generous reward. Although about thirty fell to their deaths, the remaining 270 startled Oxyartes' followers and forced surrender without a struggle.
The daughter of Oxyartes, Roxane, was widely considered the most beautiful woman in Asia, and Alexander took her as his wife. Most historians agree that he likely did not care for Roxane much more than he did for any other woman who was not his mother, but he hoped his gesture would generate goodwill among the barons of the Far East and cause the campaign to be concluded more smoothly. Indeed, one baron submitted on Oxyartes' recommendation, and the other two were defeated soon after.
Alexander's experience in the Far East was a significant period in his career. He founded a number of cities in the area in order to maintain his authority. But while the purpose of these cities was military, they also contributed to the spread of Greek culture to new lands. Alexander's experience of Asia also changed him personally. Whether because he gained a respect for Persian abilities or simply because he had indulged in the region's luxury, Alexander no longer maintained an absolute belief in Persian inferiority. He had married a Persian woman and he had supported the authority of many Persian satraps cooperatively, despite formally conquering them.
Alexander's new attitude toward Persia alienated many of the conservative Macedonian nobles, who, like Aristotle and Philip, still viewed Persians as barbaric. Two men in particular suffered for their opposition. Cleitus, one of Alexander's old friends, made the mistake of speaking his mind during a banquet where most attendants were intoxicated. Although Alexander had suspected Cleitus of treasonous thoughts, he did not intend to lose his temper and murder the man in full view of the public, as he did. Afterward, Alexander was filled with great remorse–would not eat or drink for three days–cursing himself as a murderer.
Callisthenes, the official historian of the Persian expedition, was also under suspicion. Like his uncle, Aristotle, Callisthenes viewed all Persians with contempt and disliked Alexander's change of attitude. Alexander had recently instituted a new policy requiring subjects to prostrate themselves before his feet. Though such a practice was standard for Iranians, it seemed blasphemous to Greeks, who showed such respect only to the gods. Nevertheless, Alexander's goal was to emphasize that he was king both of Macedonia and Asia. Callisthenes failed to comply and refused to prostrate himself, whether purposely or not. Alexander, noting the light applause that accompanied Callisthenes' insubordination, realized that an example would have to be made. Before long, Alexander had an opportunity to indict Callisthenes in a conspiracy in which one of Callisthenes' students had been involved–though, as in Philotas's case, the link was extremely dubious. Callisthenes was executed and immediately achieved martyr status, particularly among Aristotle's school at Lyceum. It remains unclear whether Alexander was justly protecting himself from potential conspirators or unnecessarily removing harmless opponents. In any case, his severity did contribute to the preservation of his rule.