Through guile and cunning, and more than a little brute force, Cywin took control of all the gangs in Cherico and was soon running the racketeering operation in Vorsprangs Bridge. He endeared himself to the local population by praying on the richer members of Vorsprangs Bridge society and helping the poor where he could.
Wanting to expand his fortune, Cywin became a merchant adventurer, his opponents called him a pirate and began to develop trade links and contacts across Aqshy and the other mortal realms. But his fortune and power seemed to increase dramatically after a visit to Anvilgard shortly before it was captured by Morathi. It is assumed that this is when he crossed paths with Lord Dracothfoote.
Cywin’s military career is shrouded in mystery. He is declared to be a war hero for his part in fighting the Chaos forces but he didn’t receive any awards or medals. When questioned about this lack of medals he simply replies “All who fight the forces of Chaos are heroes.” When he stood for mayor the Dinorwig Daily newspaper sent a reporter to the military records office, but the storeroom where the records were held caught fire with the reporter somehow trapped inside. Sadly the reporter died and all the military records were destroyed before the fire could be put out.
The Dinorwig Daily has held a grudge against Cywin ever since.
With his support amongst the poorer classes, Cywin won a landslide victory over the corrupt incumbent and promptly set about taxing the rich and using the money on civic projects to improve the lot of the common citizen, thus ensuring his continued election as Mayor. With his contacts across the realms, he used his influence to funnel trade through Vorsprangs Bridge, increasing the city’s wealth and his own influence even further.