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Trollsboro (theme) is an independent anarchic city-state. New Wikisburg claims that it is a borough of New Wikisburg, but does not try to control it because the effort would be too costly. Trollsboro is a lawless land that is the refuge and home of many trolls fleeing from wikis. Users are strictly forbidden to enter Trollsboro but some do anyways to participate in the black market.
Modern Trollsboro used to be the central borough of Wikisburg, the capital of the Super Mario Wiki. Wikisburg was famed for its glistening glass towers and huge dams, but most famous of all was the Great Wikisburg Wall. The Wikisburg Wall was a great steel wall that surrounded nearly all of Wikisburg to keep out trolls. However, this wall mostly just caused havoc for people leaving or entering the city, partly because of stringent security checks. The wall also caused many poor users who could not afford to leave the city to be trapped since there was a toll to go through the wall. The city's government claimed that no place in the world was safer from trolls due to the wall.
The city had one glaring weakness: the harbor. Security was much less stringent for water travel, which later proved to be the downfall of the city. Various troll gangs gradually infiltrated Wikisburg via the harbor. Instead of strengthening water security, the sysops made the Great Wikisburg Wall illegal to enter and exit. Trade suffered and citizens realized they were trapped. With the Wikisburg economy failing, many city officials struck up deals with the troll gangs for money, and corruption increased to the point where the sysops were in danger of losing control of their city. Bitter users nicknamed the city Trollsburg and said that if the trolls kept gaining control, they would drive out the users and rename the city to Troll Town. As the nickname spread it was eventually corrupted into Trollston.
To try to contain the trolls, Porplemontage set up the MarioWiki State Police, headed by DarkInsanity, but after DarkInsanity retired, his successor, Sir Grodus, was unable to control the giant organization. Eventually Wayoshi became head of the MWSP, and enacted tough reforms, but by then it was already too late and the civil population was in a great depression and was seething with revolt. Porplemontage succumbed to the pressure and decided to allow anyone to travel through the Wall, but too many people tried to get out at once. The users then shouted for the Wall to be torn down, and Porplemontage had no choice but to demolish it. With this, many citizens fled to the nearest city, Leet Town. On their way, they were attacked by trolls, and MWSP Vice-Chiefs Phoenix Rider and Son of Suns were sent in with most of the MWSP forces to control the riots. With most MWSP helping the refugees or in Wikisburg, many trolls attacked the MarioWiki in many points to spread the MWSP even further. This led to a lack of security in Wikisburg, which was taken advantage of by trolls, infiltrated the city and overpowered the MWSP. They quickly gained support of the troll gangs and drove the sysops to Leet Town.
The town was renamed Trollston, and a civil war soon broke out between the troll gangs over control of the city. Porplemontage took this chance to start up many user guerrillas to further destabilize the city. Eventually, a guerrilla led by HK-47 broke several dams above the city. The flood destroyed almost all of Trollston, and users were quick to drive out the trolls and rebuild the ruins, renaming the city New Wikisburg. Most of the trolls fled to the central borough, which remained in troll control since it was only connected to the rest of New Wikisburg by a nearly-destroyed bridge. People started calling it the Troll's borough, and eventually it was called Trollsborough.
The users proclaimed that Trollsborough was illegal and tried to invade it, but the trolls had recovered their strength and drove them out. The trolls proclaimed that the borough was the de facto independent city-state of Trollsboro, but New Wikisburg said that it was simply a borough of New Wikisburg with no independence whatsoever. By this point, new troll gang wars had reduced Trollston to anarchy, and Wayoshi deemed that Trollsboro was a weak threat and it would be too costly to invade it. Trollsboro's civil wars gradually ended and a sort of lawless crime-ridden anarchy prevailed, the closest thing to authority being several gangs and a mafia or two who clash often.