Where the First Empire was born of a remnant of the Student Men, on the eastern coast of Bluewine Bay on the Telsion peninsula and the Dragons Teeth a new civilization emerged from the ground up from the Dark Ages following the War of Four Centuries. Between 3000 and 2600 BIA Small towns and villages grew into City-States with some aide from trade with the resurgent Qanthrathi states to the west as well as trade contacts with Dwarven States, the High Elves and even the Drow (when they were not attempting to enslave them). Power in these states was distributed. A few of them had ruling dynasties but none of them ever developed a formal nobility or the rigid feudal structure. Far more common among Telsionic city state were oligarchies (in which a wealthy elite could vote on matters and their elected leaders) and democracies (in which all adult male citizens could vote on matters and their elected leaders), though slavery was widespread among them. The Drow fought with them on occasion, but were more concerned with dealing with orcish clans, hunting down Necrites and fighting wars with each other and with High Elvish raids. A few of their cities were reaped, especially early on, though eventually the Drow found it more productive to extort tribute out of these states and to use them as a source of mercenaries.

It was from this extortion that a power arose. With the persuasion of the famous statesman Ferrenes the Younger five of these city states came together in 2525 BIA with a proposal to two of the three neighboring Drow states: they would collect tribute for them from other states in return for a 8% cut, to which the Drow agreed. Thus was born the League of Five. Working together these five states could match any other state and with the profits they gained from extracting tribute their cities grew wealthier and stronger and continued to do so for five years. Their influence waxed as they vassalized other city states as 'junior members' of their league. Eventually in 2398 BIA their power had grown to the point where the Five Archons of the League told the Dark Elvish tribute collection party that they would no longer be their loan collectors. The Drow launched an attack to deal with this insolence, but this attack was repulsed. Two years latter they launched a second assault bringing to bear much larger forces, but these too were ultimately repulsed with the assistants of the High Elves. Having survived it's first trial by fire The League of Five had emerged as the Second Empire, which would continue a gradual expansion.

The Second Empire was a very loosely nit society. Junior members and client kingdoms were mostly free to run their territories as they saw fit, though they were required to pay taxes to the League and provide troops and ships when requested. The armies of the League were similarly diverse as each nation was usually free to raise warriors as it saw fit and came to include charioteers, slingers, crossbowmen, axemen, foot and mounted archers, shock infantry armed with fearsome warscythes, axes, men armed with primitive flame throwers and firebombs and elephant riders. Dwarvish minorities. Even so the most common soldiers in their armies were Hoplites: citizen soldiers clad in either linen, leather, chainmail or plate with large round shields and spears who fought in tight phalanx formations. The greatest (or at least most prestigious) hoplites came from the League's five ruling cities, where every free man was required to train for war and serve if called for. The Second Empire was very unusual in that it had five capitals which rotated on an annual basis. Eventually the government turned to subsidizing armaments. League policy was set by two bodies, the Council of Archons (which had five members elected by the people of each of the five cities) and the League Assembly (representatives of each of the League's Junior members, which included some colonies created by the Senior Members). The League Assembly did have some power and influence, in particular over budgetary matters even though the Council of Archons still served as the executive wing. In addition to the League Members there were also League Subjects who had resisted the League and were stripped of their right to assembly, usually for periods of 50 or 100 years.

Though the Second Empire fought several wars with the Drow ultimately it avoided too much confrontation with them. Fearing what happened to the First Empire they repulsed Drow attacks and fought battles at sea, but never launched an attack on a Drow State itself, in spite of considerable prodding from the High Elves. There was also a fair amount of trade between the second empire and the neighboring Drow States. Though a few sources embellish it most the role the Dark Elves played in it's end was secondary, for ultimately the Second Empire collapsed from within.

In 1979 BIA, Triaxicles (Strategos of the Southern Seas) in one of seventh and final war between the Second Empire and the Halicanisid Seraphate. From the Empire's assets on the eastern coast of the Greenwater Sea he launched an invasion, bested armies four times the size of his and (with reinforcements from the Empire Proper) pushed into the heart of the Second Empire's long time rival. In three years he had conquered the bulk of the Seraphate and left the rest to break apart. He was recalled in 2874 BIA to stand before the five Archons and was offered a boon from the Council of Archons of anything they could provide. What he asked for was that the League of Five become the League of Six, with his own city becoming a senior member of the League along with the five founding member states. This request was refused and he refused any other boon offered to him. This move intensified a rift between the alliance's Senior and Junior partners and after Triaxicles' assassination in 1968 BIA (who was responsible for doing so has been a subject of scholarly debate to this day) eventually culminated in civil war.

Thirty Seven junior members went out and formed The League of Thirty Seven to contest control of the league from the old capital. Fighting continued as border regions declared independence from the league, were over run by barbarians, were reaped by Dark Elves (who also acted as mercenaries for each side while for the most part refusing to fight other Drow forces). After thirteen years of fighting and the deaths of millions of subjects, the League of Five had lost more than 70% of it's territory, with 30% of it's former territory in the hands of the League of Thirty Seven and the remaining 40% lost to both. It's wealth spent, most of it's best forces dead and large sections of it's farmland and infrastructure in ruins and much of it's forces dedicated to garrisoning contested territory and guarding new boarders the Second Empire was left vulnerable and would continue in decline for another twenty years until the forces of the ascendant Third Empire came and absorbed what remained.