There were 5 kings led Sumenep and now led by a regent, until today 14 regents have led Sumenep.

Arya Wiraraja Period
Arya Wiraja was inaugurated as the first Sumenep Adipati in 31 October 1269, the anniversary of Sumenep regency. When led by Wiraraja, there were developments in the regency. He came from Nangka village in East Java, he was competent leader. He was an expert in strategy and his has sharp analysis and people think he was a dukun. Wiraraja built Majapahit Kingdom with Raden Wijaya and destroyed Tatar troop in Java. When he was 35 years old , his carrier was very good. He became Demang in SIngosari and then promoted by Kertanegara (king of Singosari) as Adipati of Sumenep. and then promoted by Raden WIjaya as Rakryan Menteri in Majapahit and settled in Lumajang. After Wiraraja left Sumenep, the region declined. His authority was given to Arya bangah and the palace was moved to Batuputih to Banasare in Sumenep as well. After that then replaced again by Arya Danurwendo, and the palace was moved to Tanjung village. Next leader was Arya Asparati, and Panembahan Djoharsari. The next successor is panembahan Mandaraja who had two sons pangeran Bukabu which replaced his father and moved the palace to Bukabu (Ambunten district) and later replaced by his brother Pangeran Baragung and palace was moved to Baragung (Guluk guluk district).

Pangeran Jokotole (Pangeran Secodiningrat III)
He was the 13th king of Sumenep for 45 years  (1415-1460). He and his brother, Jokowedi were born from raden Ayu Potre Koneng, the great grand daughter of pangeran Bukabu from spiritual marriage (by dream) with Adipati Adipoday (12 th king of Sumenep). As people did not belief in spiritual marriage, her parents were angry and was about to be punish with dead sentence. Since her pregnancy, there were various peculiar things happened. After the birth, the baby was put in forest by servants of Potre Koneng. The baby was found by Empu Kelleng and was milked by his bull.

Jokotole’s birth was also happened to his brother;s birth, Jokowedi. Jokotole had supernatural power since he was kid, like he could make various households items without any equipments and the results were better than his foster father. With the power he helped smith workers including when his foster father should make a huge gate for Brawijaya VII. It said that he burned himself and then became flame and from his belly button secreted a white liquid which was used to weld the gate. He was rewarded with gold and coins as heavy as his body. Finally he served Majapahit for several years.

When he served Majapahit, he was taken as Majapahit patih’s daughter’s husband. When he arrived in Sumenep he was with his wife Dewi Ratnadi and met his mother Potre Koneng and then iinaugurated as Sumenep King as Pangeran Secodiningrat III. In his period he involved in war against Bali king, Dampo Awang, and finally won by Jokotole, as Jokotole could take the power of Dampo Awang. He was replaced his oldest son,  by Arya Wigananda in 1460.

Raden Ayu Tirtonegoro and Bindara Saod
Raden Ayu Tirtonegoro was the only woman led Sumenep, as 30th leader. According to tale, RA Tirtonegoro dreamt that queen should marry to Bindara Saod. And he became the queen’s husband and entitled as Tumengggung Tirtonegoro. There was a tragical event during her reign, Raden Purwonegoro, the patih of Sumenep loved Queen Tirtonegoro, that he hated Bindara Saod even he planned to kill him. Raden Purwonegoro came to palace and then did swing his sword but he could not get his targetm and his sword was stuck on pillar, he was then killed by Manteri Sawunggaling and Kyai Sanggatarona. Quirtonegoro and Purwonegoro were the descendants of Tumenggung Yudonegoro, 23rd king of Sumenep. Because of this Sumenep royal family was split into two groups, the queen’s side could stay in Sumenep and changed their titles into Kyai and promised to abide Bindara Saod until his 7th descendants. Other group was allowed to leave Sumenep and returned to Pamekasan, Sampang or Bangkalan.

Panembahan Somala
Bandara Saod and his first wife in Batu Ampar has 2 children. When both came to palace as invited by the queen, the second son, Somala bowed first to the queen and the first son bowed first to his father ,Bindara Saod. And then issued testament that later if Bindara Saod died the one who had right to be king was Somala. 8 days after BIndara Saod died, the queen died in 1762 and as written on the testament, Somala became king of Sumenep with title Panembahan Notokusumo I.

There were important events during Somala’s period, such as assaulting Blambangan and could won over Blambangana and Panarukan. He then built Sumenep palace, currently functions as Pendopo. He built Masjid Jami in 1763 and Asta Tinggi (royal cemetery).

Sultan Abdurrachman Pakunataningrat
Sultan Abdurrachman Pakunataningrat original name was Notonegoro, son of Panembahan Notosumo I. He was given title as doctor of literature from Bristist govt as he helped Raffless to translate old writtings into malay language. He knew Sanskrit and Kawi , he has good knowledge as well, beside is he is keen to make keris. He was known as wise and caring king.