Sharing Alexander’s upbringing, Hephaestion would have learned to fight and to ride well from an early age. His first taste of military action was probably the campaign against the Thracians while Alexander was regent (followed by Philip II’s Danube campaign 342 BC) and the battle of Chaeronea 338 BC while he was still in his teens. His name is not mentioned in list of high ranking officers during the early battles of Alexander’s Danube campaign 335 BC, or the invasion of Persia, and nor are the names of Alexander’s other close friends and contemporaries, suggesting that their promotions, when they achieved them, were earned by merit.
Hephaestion’s career was never solely a military one. Right from the start, he was also engaged in special missions, sometimes diplomatic, sometimes technical. The first mention of his career in the sources is a diplomatic mission of some importance. After the battle of Issus 333 BC, when Alexander was proceeding south down the Phoenician coast and had received the capitulation of Sidon, Hephaestion was “… authorised to appoint to the throne the Sidonian he considered most deserving of that high office.” Hephaestion took local advice, and chose a man distantly related to the royal family, but whose honesty had reduced him to working as a gardener. The man, Abdalonymus, had a successful royal career, fully justifying Hephaestion’s choice.
After the siege of Tyre 332 BC, Alexander entrusted his fleet to Hephaestion, who had orders to skirt the coast and head for Gaza, their next objective, while Alexander himself led the army overland. Hephaestion’s task was not an easy one, for this was not the Athenian fleet with which Alexander had started, and had earlier disbanded, but a motley collection of semi-reluctant allies of many nationalities, who would need holding together with patience and strength. Furthermore, on arrival at Gaza, the cargo of siege engines had to be unloaded, transported across difficult terrain, and reassembled.
Plutarch, while writing about Alexander’s correspondence, reveals an occasion when Hephaestion was away on business, and Alexander wrote to him. The subject matter suggests that this took place while they were in Egypt. What business Hephaestion was attending to we do not know, but Andrew Chugg has suggested that it was concerned either with his command of the fleet or Athenian diplomacy. He quotes sources which suggest that Hephaestion had been approached by Aristion of Athens to effect a reconciliation between Alexander and Demosthenes, and certainly, Athens’ inaction during the revolt of the Spartan king, Agis, would seem to support the idea. As Chugg says, “If he did persuade Alexander to reach an accommodation with Demosthenes at this critical juncture, as would seem likely from the circumstances, then he was significantly responsible for saving the situation for Macedon in Greece by preventing the revolt of Agis spreading to Athens and her allies.”
It is likely, though not certain, that it was Hephaestion who led the advance army from Egypt to bridge the Euphrates river. Darius of Persia sent Mazaeus to hold the opposite bank while the bridging work was in progress. This Mazaeus was the commander who threw away what looked like certain victory on the Persian right at the battle of Gaugamela 331 BC, and later became Alexander’s governor of Babylon. Robin Lane Fox has an interesting suggestion that conversation with Hephaestion may have won Mazaeus over: “It is conceivable that the battle of Gaugamela was partly won on the banks of the Euphrates and that Mazaeus’ reinstatement was less a sign of magnanimity than of a prearranged reward.”
It is at Gaugamela that mention is first made of Hephaestion’s rank. He is called the “… commander of the bodyguards (somatophylakes).” This is not the Royal Squadron, whose duties also included guarding the king in battle, and which was at that time commanded by Cleitus—a man of the older generation—but a small group of close companions specifically designated to fight alongside the king. Hephaestion was certainly in the thick of things with Alexander, for Arrian tells us he was wounded, and Curtius specifically mentions that it was a spear wound in the arm.
After Gaugamela, there is the first indication that Alexander intended reconciliation with the Persians, and that Hephaestion supported him in this unpopular policy. One evening in Babylon, Alexander noticed a high-born woman obliged to dance as part of the entertainment. Curtius explains: “The following day, he (Alexander) instructed Hephaestion to have all the prisoners brought to the royal quarters and there he verified the lineage of each of them.”Alexander had realised that people from noble families were being treated with little dignity, and wanted to do something about it. That he chose Hephaestion to help him shows that he could rely on Hephaestion’s tact and sympathy. Yet Alexander could also rely on Hephaestion for firmness and resolve. When his policies had led to a plot against his life, the possible involvement of a senior officer, Philotas, caused much concern. It was Hephaestion, along with Craterus and Coenus, who insisted on, and actually carried out, the customary torture.