Johan has already name-dropped Singapura, which will likely be a very powerful OPM located in present day Singapore at the tip of the Malay peninsula. The historiography of Singapura is somewhat complex as there are very limited historical records especially about the earlier period. The chief source is the Sejarah Malayu or Malay Annals, the annals of the Malaccan Sultunate, but we don’t know how much of the description here is fact. The second best source is A Brief Account of Island Foreigners 島夷誌略 by Yuan merchant Wang Dayuan, which only has a short section about Singapura. The third best source is from Portuguese explorers recording the oral history of the region after the fact. After that, all we really have is archaeological artifacts, a few oblique references from Vietnamese / Indonesian / Thai texts, and folk tales.

The island of Singapore has two special advantages that even today allow it to lay claim to be the trade capital of the world. Its position at the very tip of the Malay peninsula means that ships passing between China and everywhere from India, the Middle East, Africa, Australia, Europe through the Suez Canal, and the East Coast of the Americas need to pass through Singapore. The second is the harbour, which is very deep and can support the largest ships of the deepest drafts in large numbers. Shielded by island chains in every direction, Singapore is a natural defensive chokepoint with predictable weather and no natural disasters.

Singapura was supposedly founded in the late 13th century by Sang Nila Utama, a Hindu prince of the Srivijayan Empire based in Palembang. Tradition has it that he was the son of Sang Sapurba, a mythical Malayan hero said to be descended from Alexander the Great’s marriage to a Persian princess (the Annals gives his Arabic name Iskander Zulkarnain or Alexander the Two-Horned One), the Chola Rajas of South India, and Genghis Khan through the Yuan Dynasty. The famous founding myth of Singapura is that he saw a lion on the island and named it singa-pura or lion city. There are A LOT of holes in this myth. Many states in Malaya claims descent from Sang Sapurba (not uncommon - compare with every Chinese emperor claiming to descend from the Yellow Emperor). There are no lions in Singapore. There is archaeological evidence of an existing polity already located in Singapore before the alleged date (it actually shows up on Greek maps in the 2nd century). The Annals claim that Sang Nila Utama was also descended from a mermaid - the usual stuff. This is largely because the purpose of the Malay Annals was not to accurately record history, but to create a prestigious genealogy for the Malaccan Sultanate drawing from every prestigious Ancient world - Hellenic, Persian, Brahamanic, Chinese, Malay, and even the sea itself. It is hotly debated whether Sang Nila Utama ever even existed.

What is known is that the period of Sang Nila Utama’s supposed reign 1300-1347 was a prosperous one. Wang Daoyuan wrote of a large port already inhabited by many Chinese people in 1335, where the markets overflowed with ironware, spices, silks, porcelains, hornbills, cotton, and sandalwood, including goods flowing to/from the Southern Chinese main trading port at Quanzhou. Yuan Dynasty records document tribute missions from Singapura in 1325 carrying elephants, amber, and diamonds. What is immediately clear is that none of these goods are produced in Singapura and the immediate vicinity, which means by this point Singapura was already a bustling and active entrepôt trading hub. This flourishing trade also tied Singapura closely to the Yuan Dynasty, and records indicate that a Yuan fleet was dispatched to end an attempted siege by the Siamese in 1337.

Sang Nila Utama was succeeded by Sri Wikrama Wira in 1347. To the east, the Majapahit was experiencing its golden age. Once a relatively relaxed trading empire, the new prime minister Gajah Mada had declared in 1336 a grand plan to conquer all of Maritime South East Asia. A smaller Majapahit invasion of Singapura was fought off in 1339, but in 1348, Majapahit envoys arrived with a snarky message. The Raja of Singapura was presented with a wooden ring and asked if there were better craftsmen in Singapura. The ring was an oblique message, that Majapahit believed Singapuran soldiers fought like women and would be easily conquered. The Raja replied that they could shave the hair off a boys head, and sent an axe back, another oblique message that a Majapahit invasion would be met with violence. Records are a bit mixed. Both sides agree that there was a large invasion involving at least 100 ships, and that a major battle was fought, after which Majapahit withdrew. However, Majapahit records in 1365 include Singapura as part of the Majapahit thereafter, while the Malay Annals continue as normal.

This confusion over what happened and who won needs me to be considered within the framework of what we now call the mandala system. Despite the influence of centralised states in other parts of Southeast Asia and especially China, the Malayan states functioned more like a decentralised mafia family. Each state had a core kingdom built around a city as a centre; other kingdoms, cities, and villages radiated outwards from the centre in varying degrees of actual control. Which mandala you were in was largely manifested by the sending of tributes and providing soldiers in times of war. Mandalas were very personal, often involving personal friendships / enmities, which meant they correlated closely with the strength and charisma of individual rulers. The battle may hence have been settled by offering war reparations from Singapura, interpreted as a tributary relationship by Majapahit. The other likely explanation was that Singapura indeed lost, and fell under Majapahit rule thereafter.

History at this point gets a bit murky. The Malay Annals say that Sri Maharajah succeeded the throne in 1375. He was depicted as a foolish and cruel king. Singapura was besieged by garfish, a type of fish with a hard beak prone to jumping out of the water at high speeds and even today occasionally responsible for some deaths. The soldiers of Singapura struggled to contain the scourge of the fish, until a young boy suggested using banana tree trunks as a wall to stop the fish. While this worked, the Raja was embarrassed that a boy solved the problem where he did not and had him executed. After the death of Sri Maharajah, Iskandar Shah succeeded the throne in 1387 and converted to Islam. One of his concubines, the daughter of the prime minister, was framed by the other women in the palace for infidelity, and in a rage Iskandar Shah had her impaled in the market. The prime minister was outraged and sent a secret letter to Majapahit, opening the gates of the city to a massive invasion force. Iskandar Shah escaped and managed to found a new kingdom in Malacca, which ultimately became the Malacca Sultanate, one of the major powers of the region for centuries to come.

Historians generally believe all of that last paragraph was fiction. Portuguese and Chinese sources from the period tell a very different story. They say Malacca was founded by a pirate from Palembang (sound familiar?) with the title of Parameswara who led his men to Singapura pretending to serve the court. He was welcomed, but turned around and assassinated the Raja, ruling for 5 years before Majapahit (or potentially Ayuthaya) invaded. This shameful history needed to be whitewashed. Sri Maharajah was invented to make it seem like he succeeded an evil monarch and restored justice to the country, and Iskandar Shah was invented to provide some background for Islam and a royal lineage. What is clear is that Singapura by this point was in decline, probably due to the fall of the Yuan dynasty and the rise of the new Ming dynasty, who had strong trading relations with Majapahit and worked to actively bypass Singapura.

In Malacca, Parameswara played his cards right and built an extremely strong relationship with Ming China. The founding of Malacca coincided with the great Ming treasure fleets of Zheng He, who set sail 7 times between 1405-1433 from China reaching as far as South Africa, in what was the largest fleet that had ever sailed. The fleets were laden with vast amounts of treasure meant for exchange and collection of tribute, and carried enough soldiers to invade any country that didn’t submit. Parameswara acted fast, promising to dedicate great resources to supplying his fleet in harbour in exchange for recognition as the ruler of Malacca. In 1411, he brought the entire royal family and a large embassy laden with multiple ships to the Nanjing to pay homage, which became a tradition for subsequent Malaccan rulers. This was a masterstroke, putting him within the Chinese mandala and offering great protection against future Ayuthaya and Majapahit incursions. Unlike Majapahit, China only demanded tribute and trade, gave out enough gifts to repair the royal treasury, and was not in the habit of being coercive. Acknowledgement from Ming brought Malacca much needed legitimacy, elevating it from a pirate state. When Ayuthaya grew too powerful and began threatening surrounding countries, Malacca sent envoys to the Ming court, who responded with warnings against Ayuthaya, proving that the system worked.

Unfortunately with the accession of the Zhengtong Emperor in 1435, China turned rapidly inwards and Malacca was left to fend for itself again, though by now rich as a major trade hub and powerful navy. The Yingzong Emperor Zhu Qizhen is well remembered for attempting to lead an army against the Oirat in 1449, getting captured, and being deposed by his own brother while in captivity. Sensing weakness, Ayuthaya launched multiple invasions of Malacca in 1446 and 1457, which were successfully fought off, destroying the Ayuthayan navy and ushering in Malacca’s Golden Age. By this point, Ming had stabilised again and trade was plentiful. Malacca began its on mandala, expanding to include surrounding trading states. In 1481, on request from Ming, it even provided military support to Lan Xang against a Vietnamese invasion. This would continue until the conquest of Malacca by Portugal in 1511.