Another user @Lemister@hexbear.net, has mentioned Michael Hudson, and though I haven’t read his books on the ancient economy they are on my list. He mentions ancient economies and tyrants in some articles you can find online. To give you a gist, here are some quotes from Michael Hudson: The End of Western Civilization – Why It Lacks Resilience, and What Will Take Its Place

Some families created mafia-like autocracies by monopolizing the land and tying labor to it by various forms of coercive clientage and debt. Above all was the problem of interest-bearing debt…

Out of this situation Greek reformer-“tyrants” arose in the 7th and 6th centuries BC from Sparta to Corinth, Athens and Greek islands. The Cypselid dynasty in Corinth and similar new leaders in other cities are reported to have canceled the debts that held clients in bondage on the land, redistributed this land to the citizenry, and undertaken public infrastructure spending to build up commerce…

This autocracy vs. democracy rhetoric is similar to the rhetoric that Greek and Roman oligarchies used when they accused democratic reformers of seeking “tyranny” (in Greece) or “kingship” (in Rome). It was the Greek “tyrants” who overthrow mafia-like autocracies in the 7th and 6th centuries BC…

And another Hudson article on the Ancient economy you may find interesting, from Michael Hudson: Debt, Economic Collapse and the Ancient World

The former rival general said just what a classical Greek tyrant Thrasybulus advised in the 7th century BC to his contemporary Corinthian ruler Periander who had overthrown the aristocracy, cancelled the debts that had held the peasantry in bondage and redistributed the land (which is what the Greek tyrants did, and why they were disparaged by subsequent oligarchies, who turned the label “tyrant” into an invective). When asked by Periander what to do to prevent the deposed Corinthian oligarchy from trying to recover its former despotic power, Thrasybulus walked over to an adjoining wheat field and pointed to the stalks of wheat at different sizes. He took a sickle and made a sweeping motion to make the stalks even, so that they were at the same level.

Another book on the subject is Passages from Antiquity to Feudalism by Perry Anderson. One of my favorite books. It gives a quick overview of the modes of production of Ancient Greece and Rome and then discusses how they collapsed and transitioned to Feudalism.

Here are some passages regarding Ancient Greece and the Tyrans:

After the collapse of Mycenaean civilization about 1200 B.C., Greece experienced a prolonged ‘Dark Age’

It was in the succeeding epoch of Archaic Greece, from 800 to 500 B.C., that urban pattern of classical civilization first slowly crystallized… local kingships were overthrown by tribal aristocracies, and cities were founded…

These cities were essentially residential nodes of concentration for farmers and landowners… the social organization of these towns still reflected much of the tribal past… their internal structure was articulated by hereditary units whose kin nomenclature represented an urban translation of traditional rural divisions.

The rupture of this general order occurred in the last century of the Archaic age, with the advent of the ‘tyrants’ (c. 650 - 510 B.C.). These autocrats broke the dominance of the ancestral aristocracies over the cities: they represented newer landowners and more recent wealth, accumulated during the economic growth of the preceding epoch, and rested their power to a much greater extent on the concessions to the unprivileged mass of city-dwellers.

The tyrants were the product of a dual process within the Hellenic cities … The arrival of coinage and the spread of a money economy were accompanied by a rapid increase in the aggregate population and trade of Greece… The economic opportunities afforded by this growth created a stratum of newly enriched agrarian proprietors, drawn from outside the ranks of the traditional nobility…

At the same time, the increase of population and the expansion of disruption of the archaic economy provoked acute social tensions among the poorest class on the land… The combined pressure of rural discontent from below and recent fortunes from above forced apart the narrow ring of aristocratic rule in the cities. The characteristic outcome of the resultant political upheavals within the cities was the emergence of the transient tyrannies of the later 7th and 6th century… Their victory, however, was generally possible only because of their utilization of the radical grievances of the poor, and their most lasting achievement was the economic reforms in the interests of the popular classes…

The tyrants, in conflict with the traditional nobility, in effect objectively blocked the monopolization of agrarian property that was the ultimate tendency of its unrestricted rule… small peasant peasants farms were preserved…

Something interesting to note is that this trend of tyrants was common throughout Greece, but was essentially absent in Rome. Rome didn’t have an age of tyrants (or if they did as Hudson suggests the Roman kings were analogous to tyrants, they were not ultimately successful and the nobility was able to hold on to power till the end.

Anderson remarks:

In one critical respect, however, Roman expansionism distinguished itself at the outset from Greek experience. The constitutional evolution of the city conserved aristocratic power right down and into the classical phase of its urban civilization… unlike the Greek cities, Rome never knew the upheaval of tyrant rule, breaking aristocratic dominance and leading to subsequent democratization of the city, based on a secure small and medium agriculture.

Class struggle is essential in understanding ancient history. Reading Hudson and Anderson really makes it clear how “The history of all hitherto existing society is the history of class struggles”