Pisistratus (circa 600 to 527 BCE), or Peisistratus, was an ancient Greek tyrant who ruled the city-state of Athens. Initially a student of the lawgiver and political philosopher Solon, Pisistratus presented himself as the champion of the poor, disenfranchised masses of Athens, and used their support to seize power in 560 BCE. Though he was ousted from the city five years later, he was twice reinstated and came to power for the third and final time in 546 BCE. He ruled as a tyrant, which, in the ancient Greek context, did not necessarily carry the negative connotation it has today, but merely referred to a ruler with near absolute power. As tyrant, he appeased the poor by granting them new farmlands and spent the final years of his rule developing the city of Athens itself, facilitating the growth of trade, religion, and culture. When he died in 527 BCE, he was succeeded to the tyranny by his two sons, the Pisistratids.

Not much is known about Pisistratus' early life, except that he was born in the deme of Philaidae in eastern Attica to a man named Hippocrates, sometime around the year 600 BCE. According to Herodotus (circa 484 to 425/413 BCE), Pisistratus' father went to the Olympic Games as a spectator a few years before his son's birth (probably in 608 or 604 BCE), where he made a sacrifice to the gods. During the sacrifice, the cauldrons that had been filled with the meat and water boiled and overflowed, even though the fire had not yet been lit. This was witnessed by Chilon of Sparta, who took Hippocrates aside and told him that this was a divine omen. He warned Hippocrates to avoid bringing a childbearing wife into his household and to send her away if he already had one. At the very least, Chilon told him that he must avoid having a son and must immediately disown any son that might be born to him. Hippocrates, of course, did not heed Chilon's advice.

Pisistratus grew into a handsome, intelligent young man. As a teenager, he became a close disciple of the Athenian lawgiver Solon (circa 630 to 560 BCE), a relative of his mother's, with whom he may have had a sexual relationship. It was common in those days for a mature man in his 20s or 30s to take a teenage youth under his wing in a relationship that was partly instructive and partly erotic; the older man was known as the erastes, the younger man as the eromenos. As historian Anthony Everitt notes, Solon certainly engaged in this kind of relationship and, indeed, may have been thinking of Pisistratus when he wrote some of his erotic poetry. In one such poem, the Athenian lawmaker writes about falling in love "with a boy in the lovely flower of youth / desiring his thighs and sweet mouth" (quoted in Everitt, 73). But whatever the exact nature of the relationship between the two men, Pisistratus was clearly devoted to Solon, particularly regarding his democratic reforms. Solon, of course, was known for restructuring the Athenian law code that had been initially set down by the tyrant Draco; his reforms included a reconstituted class hierarchy, new democratic political institutions like the Council of 400, and the elimination of debt slavery, among others. Pisistratus fervently supported these reforms to the point where, according to Plutarch, he was "an extreme democrat" (quoted in Bauer, 519).

In the 560s BCE, Athens entered a dispute with the city-state of Megara over control of Salamis, a rocky island two miles (3 km) off the coast of Attica. Solon and his supporters believed that control of the island was paramount for the protection of Athens' lucrative olive oil trade and began drumming up support to seize it from Megara. "Let us go to Salamis," wrote Solon, "to fight for a beautiful island / and clear away bitter disgrace" (quoted in Everitt, 72). Pisistratus, too, supported the annexation of Salamis and carried his mentor's message to the Athenian citizenry. Before long, the Athenians were persuaded to declare war on Megara. Solon himself led the military expedition to Salamis and, through either trickery or a battlefield victory, triumphed over the Megarian army in 565 BCE; Pisistratus, who served as an officer on Solon's staff, was wounded in the campaign. Despite its defeat, Megara refused to relinquish its claim on the island, and arbitration was handed over to Sparta. But thanks to Solon's eloquent arguments, the Spartans were convinced to judge in favor of Athens, and Salamis was handed over to Athenian control.

After the war with Megara, Pisistratus emerged as a prominent figure in Athens. Now around 35 years old, he was in the prime of his life and was renowned both as a disciple of Solon and as a war hero who had suffered a wound in service to Athens. He had, moreover, developed into a very charismatic man. According to Plutarch, "there was something subtly charming in the way he spoke…he was so good at simulating faculties with which he was not naturally endowed, that he was credited with them, more than those who really did have them" (quoted in Bauer, 519). Because of these factors, he became popular amongst the thetes, the poorest and most numerous of Athens' four social classes, which began to look to him as a savior.

Playing into this role, Pisistratus broke with his former mentor by claiming that Solon's reforms had not gone far enough – what Athens truly needed, he claimed, was total democracy, in which the most impoverished and disenfranchised citizens had the same rights as everyone else. Followers of Pisistratus soon coalesced into a political faction referred to by historians as the 'Men of the Hills'. They were rivalled by two other political factions: the 'Men of the Coasts', who liked Solon's reforms and wanted to keep them as they were, and the 'Men of the Plains', a group of old, aristocratic families that wanted to concentrate power in the hands of the rich. Though the Men of the Coast and Men of the Plains hated one another, they both felt endangered by Pisistratus and his Men of the Hills, whom they saw as a threat to the whole social order.

One day in 560 BCE, Pisistratus rode into the agora (marketplace) in a chariot, quite visibly bleeding from a wound. He claimed that he had just survived an assassination attempt and accused his political opponents of having plotted against his life. As the citizens gathered to gawk at his injury, the aged Solon appeared and expressed suspicion about his former pupil's intentions. "You listen to the words of a crafty man," he warned, "but not to what he does" (quoted in Everitt, 76). That evening, the matter was taken up at a meeting, in which Pisistratus asked the Athenian people for protection, reminding them of the many services he had done them. Against Solon's misgivings, it was decided that Pisistratus would be granted a bodyguard of 50 men armed with clubs. With this small army, Pisistratus staged a revolt several days later, seizing control of the Acropolis and setting himself up as the tyrant of Athens. Pisistratus took no steps to punish Solon for opposing him; Everitt supposes that "their common, loving past presumably protected the old man" (77). Instead, the tyrant allowed Solon to continue living in the city until his death a few months later.

Having seized the reins of power, Pisistratus did not act fast enough to consolidate his new regime. The Men of the Coast and Men of the Plains both opposed his tyranny, viewing him as a dangerous demagogue. Five years after Pisistratus' initial coup, the two factions put aside their mutual hatred and joined forces, ultimately driving the tyrant into exile. But this shaky alliance proved short-lived; no sooner had Pisistratus been forced out of Athens than the Coast Men and Plains Men resumed their old bickering with one another. The cunning Pisistratus was eager to use this infighting to his advantage. He secretly got in touch with Megacles, a leader of the Men of the Coast, and offered a deal – if Megacles helped restore him to power, Pisistratus would return the favor by getting rid of the Men of the Plains. The alliance would be cemented by Pisistratus' marriage to Megacles' daughter. Reluctantly, Megacles agreed, believing that he could govern through Pisistratus.

After making their arrangement, Pisistratus and Megacles needed a way to ensure the tyrant's smooth transition back into power. What they came up with was referred to by Herodotus as "the silliest scheme I've ever heard of" (1.60). They went to the countryside and found a woman named Phya who was "almost six feet tall and strikingly beautiful" (ibid). Then, after dressing her up in armor and teaching her how to carry herself like a goddess, they had her drive into the agora in a chariot and claim to be Athena, the patron goddess of the city. "Athenians," she said, "hail Pisistratus and welcome him joyfully, since Athena herself is bringing him home to her own acropolis, honoring him above all men" (ibid). Of course, most Athenians would have known that this woman was not actually Athena but would, nevertheless, have understood the implied message of this bit of political theatre: that the tyrant Pisistratus had returned to power and that this time, he was not going anywhere.

But Pisistratus' second tyranny would be even shorter than his first. Megacles, who seems to have been a particularly fickle ally, came to regret the arrangement shortly after Pisistratus' marriage to his daughter. As it happened, the tyrant already had two fully grown sons by his first wife and did not want to risk getting his new bride pregnant, aware that the birth of another son would only complicate the matter of succession. To avoid this eventuality, he did not have regular intercourse with his wife, but only engaged with her in a manner that Herodotus blushingly refers to as "an indecent way" – by which he most likely means anal sex. The wife, says Herodotus, "kept quiet about it at first, but later (I do not know whether she was questioned about it or not) did she tell her mother, who then told her husband" (1.61). To the ancient Greeks, being on the receiving end of such sexual acts was a humiliation; Megacles, therefore, believed that Pisistratus was intentionally insulting him and his entire family. Enraged, he contacted Pisistratus' enemies and began plotting against him. When the tyrant learned of this, he knew that he would be outnumbered. Rather than wait for his enemies to strike, he fled Athens in the night, retreating with his sons to Eretria, a city on the nearby island of Euboea.

This time, Pisistratus' exile lasted for a decade. As the years caused him to fade from the collective memory of Athens, his enemies must have assumed that he was gone for good. The former tyrant, however, was not defeated, but merely biding his time as he plotted his return. He called in all the debts and favors that he had accumulated from other city-states during his years as tyrant, and took over the deserted gold and silver mines in the Pangaeum mountains in Thrace. By 546 BCE, he was wealthy enough to hire a small army of mercenaries. Backed by Athens' rival city-states – most notably Thebes – he sailed across the narrow strip of water between Eretria and Athens, landing on a beach at a place called Marathon. For months, it had been quite obvious that the former tyrant was planning an attack, and the people of Athens anxiously awaited his coming, the air a mixture of anticipation and dread.

Others did not want to wait but went to Marathon to join Pisistratus' army, betting that he would come out on top. Of these Athenians, Herodotus scathingly writes that they were "men who found tyranny more welcome than freedom" (1.62). Before long, Pisistratus' army of mercenaries and Athenian exiles left Marathon and advanced toward the city itself. The panicking Athenian elites quickly put together an army of their own to oppose him, and the two forces arrayed for battle near a sanctuary of Pallenian Athena at Mount Hymettus. Just before the fight, a seer approached Pisistratus with a divine prophecy:

The net has been cast forth, and the snare is spread open;

The tuna will swarm through the moonlit night.

(Hoerodotus, 1.62)

Pisistratus interpreted this omen favorably and turned to the task at hand, believing the gods were on his side. By this point, it was midday – the Athenians in the opposing army, having just eaten their lunch, were lounging around, either sleeping or playing dice, in the belief that Pisistratus would not attack today. So, when Pisistratus did attack, they were taken completely by surprise and were easily routed. After the battle, the tyrant sent his two sons ahead on horseback. They caught up with the fleeing Athenian soldiers and promised that there would be no reprisals as long as the soldiers returned to their homes and made no further attempts to resist Pisistratus' coming. The soldiers did exactly that, leaving nothing standing between Pisistratus and the city. The tyrant, therefore, made his triumphant entry into Athens, returning to power for the third and final time.

Having gained and lost power twice before, Pisistratus had learned from his mistakes. He confiscated all weapons from ordinary Athenians so that they could not rise against him and took hostages from the city's most prominent families, keeping them on the island of Naxos. He kept a bodyguard, comprised partially of Scythian archers, to enforce his rule and watch for any signs of dissent. However, Pisistratus did not forget that his base of support came from the poor, landless masses; he knew that to hang on to power, he must first make them happy. He set about doing this by confiscating the properties of the aristocrats like Megacles, who had opposed him. He then reorganized these lands into lots and redistributed them to those he deemed most in need, namely landless farmhands and unemployed urbanites. He offered loans to these men so that they could obtain work animals and farm equipment. By doling out these countryside farmlands and supplying the farmers with money, Pisistratus hoped to keep them so busy in the field that they had no time to pay attention to politics.

Under Pisistratus, Athenian commerce flourished. Like Solon before him, he recognized the value of the olive oil trade and encouraged the planting of new olive trees, while also facilitating trade with neighboring city-states. Attic pottery was another valuable trade commodity, with Athens soon outstripping Corinth as the main exporter of ancient Greek pottery across the Mediterranean world; indeed, black-figure Athenian pottery dating from this period has been found as far east as Syria and as far west as Spain. The wealth brought into Athens from this trade was reflected in the new coins minted during this period from silver provided by Pisistratus' own mines in the mountains of Thrace. The tyrant utilized these riches to improve the city itself, as, at this time, Athens was not yet the powerful polis it was destined to become, but rather a messy concentration of villages. Pisistratus built new roads, renovated old buildings, and improved the city's water supply by building an aqueduct that fed water to a fountain in the agora. He beautified the agora as well, giving it a majesty to reflect the glory and power of his reign.

As tyrant, Pisistratus understood the propagandic power of religion and culture, and took steps to bring both under state control. He took direct control of the temple of Demeter at Eleusis and brought all the countryside cults of Artemis into the city, where he could keep a better eye on them. He encouraged the worship of Athena as the city's chief deity and constructed an entry gate on the Acropolis that he dedicated to her. He also began construction of a temple dedicated to Olympian Zeus, though it would not be finished until the time of Roman Emperor Hadrian (reign 117 to 138 CE). Pisistratus supported the development of the Panathenaic Games, held every four years to honor Athena, which saw athletic competitions and the performances of Greek tragedy plays by poets such as Anacreon (circa 573 to 495 BCE), who took up residence at Pisistratus' court. The tyrant was greatly interested in making Athens the literary center of Greece and sponsored the first attempt at a definitive edition of Homer's epics. Indeed, Pisistratus claimed descent from Nestor, one of the mythical Homeric heroes of the Trojan War.

Pisistratus died in 527 BCE, around the age of 73, having managed to hold on to the tyranny until his death. He was succeeded by his two sons, Hippias and Hipparchus, who may have ruled jointly and were together known as the Pisistratids. They continued their father's prosperous and peaceful reign until 514 BCE, when Hipparchus was murdered in an act of personal vengeance. The assassination of his brother apparently drove Hippias over the edge, turning him into a paranoid and bitter tyrant. He ordered the banishments and executions of large numbers of people he suspected of plotting against him. Hippias' tyranny was put to an end around 510 BCE, when the Spartan King Cleomenes I (reign circa 524 to 490 BCE) marched on Athens and drove him out. Thus, less than two decades after Pisistratus' death, the reign of his dynasty came to an end, allowing steps in the direction of Athenian democracy.