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The history of Pekalongan dated back to the early 12th century. A book written in 1178 by a Song dynasty official already had record of Pekalongan, then known to Chinese merchants as "Pukalong", it was then a seaport of Java(then known as Dvapa); the king of Java lived at Pukalong, knotted his hair at the back of his head, while his people wore short hair and wrapped their body with colorfully weaved cloth. Chinese merchant ship set sail from Canton during November, with the aid of fair wind sailed nonstop day and night, arrived at Pukalong in about one month. The people made wine from coconuts, produced very delicious red and white cane sugar, the kingdom made coins out of bronze and copper, 60 copper coins exchanged for one tael of gold. Local produces included pepper, clove, sandalwood, eaglewood and white round cardamom.
Pekalongan became a part of the empire of the Sultanate of Mataram through treaty and marriage alliances by the early 17th century. The area was on the geographic periphery of the empire, which was based in interior central Java. However, it was a wealthy area, and by the end of the 17th century, the substantial money and produce it sent to the center made it a key part of Mataram's realm. The area went into economic decline during the 18th century, and the Dutch East India Company began to gain substantial influence over the area's political and economic life. The Dutch built a fort in the city in 1753; this fort still stands.
From the 1830s, the Pekalongan area became a major producer of sugar. Sugarcane had been grown in the area since early 12th century, as recorded in Chinese history books, but production expanded substantially during the mid-19th century due to Dutch efforts. Initially, production was boosted through compulsory corvée labor; the Dutch colonial government took advantage of longstanding Javanese expectations that the peasantry contributes a part of their labor to the state. Between the 1860s and the 1890s, this system was phased out, and workers were paid directly. The colonial sugar industry collapsed during the Great Depression of the 1930s, but sugar remains a key export of the area in independent Indonesia.
On October 8, 1945, an anti "Swapraja"/anti feudalism movement called Three Regions Movement/"Gerakan Tiga Daerah" was established in Tegal, Pekalongan, and Brebes. The goal of this movement was to replace the blue blood regents (related to the kings from Jogyakarta and Surakarta) with ordinary people. According to the leaders of this movement, the old regents had cooperated with Japanese during the world war II and sent people to the Japanese slave labor camps.
The main leader of this movement was Sarjiyo who became the new regent of Pekalongan. Other leaders of this movement were Kutil, K. Mijaya, and Ir. Sakirman. Ir Sakirman was the local leader of Indonesian Communist Party (PKI).
The old regents were arrested, stripped naked, and dragged into the prisons. Other government officials and police officers were kidnapped and massacred at Talang bridge. This movement also started a racial riot against ethnic Chinese in Brebes.
The government of Republic of Indonesia (RI) in Jogyakarta disagree with this movement and declared it as an illegal movement.
On November 4, 1945, the movement attacked Indonesian army HQ and the regent office in Pekalongan. The rebels were defeated by Indonesian army in a fierce battle on December 21, 1945. Most leaders of this movement were arrested and thrown into the prisons. This rebellion is called Three Regions Affair.