The most popular version of the founding of Ponorogo is the story of Raden Katong's arrival in the Wengker region to face Demang Suryongalam, who is better known as Ki Ageng Kutu. Ki Ageng Kutu is believed to have been an official or nobleman of Majapahit who was disappointed with the political and social situation in the kingdom. He felt that Majapahit had lost its glory due to weak leadership and the corruption of the kingdom's officials.
Ki Ageng Kutu then built a base of power in the Kutu area, Jetis District, which is now part of Ponorogo Regency. He managed to gather followers from among local farmers and soldiers who were dissatisfied with the condition of Majapahit. One form of his symbolic resistance was to create the Reog Art, which is full of satire towards the King of Majapahit at that time, Prabu Brawijaya V. The Lion Barong's head in Reog is considered a satire of the king who was considered to be more afraid of his concubine.
Seeing the potential threat from Ki Ageng Kutu and his followers, Majapahit then sent Raden Katong to quell the rebellion. Raden Katong was the son of Prabu Brawijaya V and the half-brother of Raden Patah, the founder of the Demak Sultanate. He was known as an intelligent figure with high diplomatic skills.
Based on the Babad Ponorogo, the arrival of Raden Katong to Wengker is estimated to have occurred between 1475 and 1482 AD, close to the period of the collapse of Majapahit which is estimated to have occurred around 1478 AD (according to the candrasengkala "Sirna Ilang Kertaning Bumi"). This indicates that the arrival of Raden Katong occurred at the beginning or not long after the fall of Majapahit.
Accompanied by Ki Ageng Mirah, his friend and advisor, Raden Katong settled in Plampitan Hamlet, Setono Village, Jenangan District to develop a plan to face Ki Ageng Kutu. At first, Raden Katong and his troops were unable to defeat Ki Ageng Kutu's forces through direct warfare. Therefore, he used diplomatic and persuasive strategies to reduce the influence of Ki Ageng Kutu. One of his steps was to spread Islamic teachings to the people in the Wengker region, which eventually succeeded in attracting many new followers.
In addition, Raden Katong also married Niken Gandini, Ki Ageng Kutu's daughter, to strengthen relations with Ki Ageng Kutu's family. This step further weakened Ki Ageng Kutu's position, until finally his power ended.
There are several versions of the end of Ki Ageng Kutu's life. Some say that he eventually made peace and surrendered to Raden Katong, while other versions say that he fled and died in exile. Some stories even mention that he died in battle.
After defeating Ki Ageng Kutu, Raden Katong established a new government center and was appointed as the Duke of the Ponorogo Duchy. According to the Handbook of Oriental History, Raden Katong was inaugurated as the Duke of Ponorogo on Sunday Pon, the 1st of Besar month in the year 1418 Saka, which coincides with August 11, 1496 AD or 1 Dzulhijjah 901 Hijriyah. This date was then designated as the Anniversary of Ponorogo Regency, which is celebrated every year by the local community.