Like many of the Tilean city-states, Tobaro was founded on the ruins of an Elven city, in this case a fortress abandoned during the War of the Beard. However, this lone city on the splintered western half of Tilea has not had the good fortune that one might imagine, given its proximity to the Estalian trade routes through the Tramoto Pass and the River Eboro. Tobaro has had a reputation as one of the unluckiest cities in all of Tilea, partially because the islands to its south as so choked with pirates that its trade has never been as rich as its fellow city-states.
Tobaro saw its glory days during the Arabyan Crusades, when the city served as the chief port and transporter for the Crusader armies seeking to retake Estalia from the Arabyeans, given its access to Estalia and Araby by both land, river, and sea. The city's finest hour came in 1488 IC, when the evil Sultan Jaffar launched his entire fleet of war dhows at Tobaro. The city's defenders held the sea walls of the outer city against an invasion fleet many times their size, forcing a humiliating retreat onto the Arabyeans that marked the turning of the tide militarily.
Unfortunately for the city, their glory was to be short-lived. In 1563, the great catacombs of the ancient High Elf fortress that the city rested on top of were breached by a massive army of Skaven, who swiftly overwhelmed the city's defenders. While the Prince of Tobaro, Meldo Marcelli, managed to escape the city with half of his army and most of his ships and Man-O-Wars, the civilian population was decimated, either killed or eaten or sent into slavery under the earth. The Prince and his remaining men landed in Remas, were he used his vast wealth to hire a vaster mercenary army, including the best soldiers of Remas.
When Prince Maldo returned to Tobaro to seek his revenge, he found himself allied to a fleet of High Elf warships who had been sent to reclaim the tombs of their relatives from the loathsome ratmen. Together, men and elves slaughtered the Skaven invaders, restored the catacombs, and sealed them off forever, leaving a specialised mercenary unit to patrol them. While the city was redeemed, the population never recovered completely, and as such Tobarans have a reputation as gloomy and macabre people, given to obsessing about death. Notably, the Cult of Morr is very popular in Tobaro.
Today, the city has regained much of its financial standing, although it has never regained its political or military power to the same extent. Part of this decline can be traced to the turbulent politics of the principality. While the Marcelli's managed to maintain their position as the royal house, the different branches fell into vicious feuding and vendetta that paralysed city government for some time.
After three centuries of this, the squabbling was halted when a prophecy was made that the next prince would die a terrible, terrible death. Not wanting such a fate, the contenders for the office agreed to elect a pig as Prince of Tobaro, named Piggolo the first, to bear the burden of office. Unfortunately for them, the Pig seemed immune from the prophecy, and ruled for many years, to great public acclaim - Piggolo I was known for his lack of corruption and meddling in the city's affairs (a model of laissez faire government), his personal conduct was a relatively moral one compared to previous princes, and in general the public seemed to have a genuine affection for their porcine liege. When the different contenders plotted to execute (or is it slaughter?) the pig, it was made very clear to them that such treason would be punished with summary execution. Thus, Piggolo the I ruled to a ripe old age, when he died by falling off the battlements of his castle while inspecting the guard. While the monarchy has moved on, the people of Tobaro still have a soft spot for their former ruler, and often an unpopular Prince will be reminded of this by the graffiti "Piggolo Lives!" scrawled on the walls.