Pre-Colonial Singapore: Temasek, Dragon’s Tooth Gate, and Singapura, 100-1819

The History of Singapore. Editor: Jean E Abshire. The Greenwood Histories of the Modern Nations Santa Barbara, CA: Greenwood, 2011.

The early history of Singapore has very limited documentation. What is known is pieced together from various sources, including legend, a semi-historical document known as the Malay Annals, archeological evidence, records from early Chinese traders, and later documents from European colonial seafarers. It is only after Singapore became a British holding that the historical record becomes clearer. However, the evidence that exists makes it clear that human inhabitation of Singapore started centuries earlier. Its early existence and its position then was a function of what has shaped Singapore throughout its history and indeed still today: Singapore’s geographic position at a crossroads for trade and the resulting struggles between different regional and global powers to advance their positions through Singapore. Indeed, globalization informed Singapore’s entire existence from its earliest days to the present, first in its advantageous position along the Maritime Silk Road, a major oceanic trade route dating back to the first millennium between East and Southeast Asia, India, the Middle East, and eventually Europe, what many scholars consider to be an early form of globalization to the intense international interconnectedness that has made Singapore the global city-state that it is today.

The early history of Singapore is, in essence, a regional history, pieced together from a variety of sources of varying degrees of accuracy and credibility. For example, a portion of the historical account is based on the Malay Annals, a history of the Malay nobility with roots in Singapore that was written on the command of Malay Sultan Mahmud Shah in the fifteenth century and prior to that was preserved via oral tradition, with storytellers passing the history of the community from one generation to the next. What one sees in reading the Malay Annals is a semi-mythological history rather than a literal account. The Annals were intended to be a record of the descent of the rulers, along with court customs and ceremonies, at a time when Malay control of the region was facing challenge by European colonial incursion. Probably motivated by an effort to aggrandize their past leaders, even to the point of suggesting a divine heritage, storytellers gave, in some cases, superhuman accounts of events and people. While it would be easy to dismiss such accounts, various aspects of the tales are corroborated by credible sources so these stories merit at least some consideration.

Srivijayan Empire, 100-1000 c.e.

The context for the settlement of Singapore has its roots in the advantageous position and role eked out by the Srivijayan Empire, which was prominent in the region for most of the first millennium. Power and influence in the region at that time were based less on control of land, as one typically sees as a mark of power, but rather control of and access to people. A ruler with greater human resources was able to grow food, create various products, and engage in other activities that provided wealth and status. Because of this focus on human resources, conflicts between groups and approaches to protecting resources were different than one would find in a land-focused society. Land was plentiful, but people were not; so rather than fighting to defend land, leaders were much more likely to simply move their people if they came under pressure or attack from a rival group. It was much easier to create a new settlement and to clear more land for farming than to find new groups of people to become workers. Thus, cities and other population centers were much less fixed than in other parts of the world, such as ancient Greece, Egypt, Mesopotamia, or China. There are few fixed monuments or defensive structures for archeologists to study because the population of Southeast Asia was too transient.

The primary activity for accumulating wealth and power was control of trade, which the geography in Southeast Asia made very easy. Trade between China and India transited through the various archipelagos that comprise Southeast Asia, with one of the most strategic bottlenecks for controlling trade being the Strait of Melaka, the southern entry to which lies about 18 miles west of Singapore. The Srivijayan Empire, which lasted from 100 to 1000 C.E., established control over much of this area and its critical trade routes. The Empire’s capital was at Palembang on the island of Sumatra in Indonesia and this served as the Empire’s primary base for centuries, although there is also some evidence from Chinese traders that another administrative center existed farther to the north. Between these two centers, the Srivijayan leaders controlled shipping, significantly aided by their control of local peoples, particularly the Orang Laut (Malay for sea people), expert seamen who provided a military-like force for the leaders.

Ships had to traverse these waters for trade, but the region was known as a dangerous place because of vicious pirate attacks, including attacks by the Orang Laut. The Orang Laut would sometimes trade, but often would surround ships in hundreds of small boats and attack for days. If the winds were favorable, the ships could sometimes escape but often not. The problem was so severe that some traders resorted to avoiding the Strait of Melaka and instead offloading goods from ships, transporting the goods overland across a narrow part of the Malay Peninsula, and then reloading them on another ship to continue on to India or China. This, however, was slow and inefficient compared to simply sailing a single ship around the Malay Peninsula through the Strait of Melaka. The Srivijayan leaders coopted some of the Orang Laut groups, turning them into followers and their boats into something of a naval fleet. This controlled the piracy problem to a sufficient degree so that sailing through the Strait of Melaka became the preferred route for the maritime trade.

With the support of the Orang Laut, Srivijayan leaders forced ships sailing between China and India to stop at the Srivijayan ports where captains were forced to pay duties, thereby increasing the wealth of the Empire. Archeological evidence suggests Orang Laut activity on Karimun Island, located west of Singapore in the middle of the southern mouth of the Strait. This activity is noteworthy, as it would be difficult to enter or exit the Strait without being noticed from a cliff-top position on the island. A later Chinese writer noted that if a ship did not stop at the required port, it might be set on by an armed group, presumably the Orang Laut, and the crew would be killed. Thus, the motivation to visit Srivijayan ports and pay their duties was high.

There is some evidence of diplomatic significance of Singapore, known as Temasek, in the seventh century, primarily as a meeting point of traders, rather than as a port. There is a tale that a Srivijanan ruler, Chulan, had become angered with the emperor of China and was planning an attack. Hearing of this, the Chinese emperor sent a ship of old men and trees to meet the Srivijayan ruler. The Chinese sailors told Chulan that they had been underway since they were young men and the trees had grown from seedlings and they had grown old during the very long voyage. Deciding that China was too distant to attack, Chulan gave up. Supposedly, this meeting took place where ships from India and China would regularly meet, at Temasek.

The Srivijayan Empire was at a point of great prosperity and power when, in 1025, disaster struck. A group from the Chola kingdom in southern India launched a raid and kidnapped the Srivijayan leader. No one heard from him again, and he presumably died in captivity. This event marked the demise of the Empire and a sharp turn for the control of the trade route. For the next century, Tamil trading companies from southern India dominated the Straits region, although the domination was weaker than the control of the Srivijayan Empire. With time, the regional trading center shifted from the old Srivijayan capital of Palambang to another trade center on the island of Sumatra, Jambi, which was the center of another kingdom, Malayu. The rise of this group of traders set some developments in motion that would eventually have significant impacts on Singapore and the region.

In particular, the Malayu had a history of engagement with China, even before the rise of Srivijaya, primarily in the areas of trade and diplomacy, and thus there was a well-established connection with China in the region. About the same time as south Indian influence waned, domestic concerns in China created a context in which the connection with the Malayu would become more important. China in the Song Dynasty came under significant pressure from the Mongols to the degree that the northern Song capital fell in 1126 and was relocated southward, creating a more prominent role in the empire for the southern Chinese. The Mongol pressure continued and Chinese leaders, motivated by the desire for better trade routes and for money to fund their defensive efforts, relaxed existing rules that restricted contact between Chinese citizens and foreigners. This made it much easier for people from southern China to initiate trade voyages resulting in settlements of Chinese people in the area of the Strait of Melaka.

The development of Chinese trade settlements in the region had several lasting effects. First, as previously noted, the earlier norm was to relocate settlements as political fortunes and strategic pressures changed, but the Chinese settlements had loyalties to leaders who were not local, thus shifting that historical dynamic. Moreover, the loyalties of the Chinese merchants to a more distant major power left them less vulnerable to the manipulations of local leaders and, thus, the very restrictive port-usage requirements that led to accumulated wealth and power for the Srivijayan Empire could not be replicated. This led to the proliferation of larger numbers of ports, rather than just a couple of monopolistic ports.

Ancient Singapore, 1299-1398

The rise of Singapore’s early prominence came in the late 1200s. The history of the establishment of Singapore as an important center is problematic in its details, as the mythicized history of the Malay Annals is the basis for accounts of its founding, the succession of leaders, and its decline. The legend claims that there was a prince, Sang Nila Utama, who was perhaps the product of a union between an adventurer king and the princess of an underwater kingdom or a descendant of a union of Alexander the Great with an Indian princess. In a mythical story, the prince and his two brothers were each given territory, and Sang Nila Utama became rajah of Palembang. Palembang became prosperous under Sang Nila Utama’s rule, but he had inherited his father’s adventurous nature and decided to set out on a voyage to seek a location to found a new city.

First he went to Bintan, an island just southeast of Singapore, where the queen, Sakidar Shah, took a liking to him, adopted him, and named him her successor. Sang Nila Utama’s time with the queen is significant, as she is allegedly the source of musical instruments that became tokens of nobility for later Malay rulers. That she was from Bintan Island likewise gave Bintan special significance in the following centuries. However, Sang Nila Utama again became bored with court life and set out again, this time to go hunting. He landed and hunted on one island, then when done, was taken by the view of an island some distance away, called Temasek. He sailed there and was disappointed to find very poor hunting, with only small animals and birds. Suddenly, a huge animal appeared and then disappeared again. His ministers informed him of an ancient lion that had a similar appearance. He decided that location would be a good one to establish his new city; and he named the location Singapura, or lion town, in honor of the lion. Sang Nila Utama set up his kingdom there, and what today is known as Fort Canning Hill became the royal residence. Sang Nila Utama was also known as Sri Tri Buana, a name which indicates he was ruler of three lands, probably Java, Sumatra, and Temasek. The oral record indicates that Sri Tri Buana, along with his ministers, was buried on the hill near the residence.

The Malay Annals do not include dates, but tracing the succession of Sang Nila Utama’s descendents and dates surrounding events during their reigns suggests the establishment of the new settlement took place in 1299. The next four descendents of Sang Nila Utama maintained their base at Singapore until misfortune befell the last of them, and the capital at Singapore was abandoned in the 1390s.

It is clear from the archeological record, however, that Singapore was an important place during that century of noble presence. Uniquely, these early Singaporeans constructed a wall of significant size; scholars have found no evidence of similar structures elsewhere in the region. While there is no clear evidence of the original intent, it is thought that the wall was a defensive barrier. One might expect that Singaporeans would be concerned about attack from the sea and that they might build a fortification to protect from that risk. However, due to its location, scholars speculate that the wall served as a defense from a land-based invasion and that the residents must have had sufficient confidence in their naval prowess to fend off a frontal sea-based assault. Further, the investment in a large, immovable structure in an area where traditionally groups relocated to contend with threats suggests early Singaporeans considered this position to be uncommonly promising as a port.

In addition, British colonists found evidence of structures built on what is now Fort Canning Hill, along with evidence of fruit orchards and terraces. Since ancient times in Southeast Asia, hills and mountains were associated with kingship and divinity. Thus, the hill that was only a little over a mile from the mouth of the Singapore River would be a logical place for the ruler to establish his residence, as suggested in the legends of the Malay Annals. The local lore when the British arrived in the early 1800s also supported the idea of a royal residence, with local people expressing unwillingness to go up on the hill, known to them as the Forbidden Hill, as it was the site of spirits. The Englishman credited with establishing Singapore as a British colony centuries later, Sir Thomas Stamford Raffles, wrote in a letter that if he died in Singapore and were buried on the hill, he would in death “have the honour of mixing with those of ashes of Malayan kings …”1 During excavations for a reservoir in the 1920s, items of gold jewelry were found, including rings, earrings, an arm band, and what was likely a head ornament. Certainly these items would much more likely have been the possessions of a royal person than common people. Excavations by archeologists in recent decades have found the remains of various ceramics, porcelain, and other objects at three different locations around the Singapore River and Fort Canning Hill. The Fort Canning Hill remains were of a higher quality than the others, offering further evidence that it was the residence of elites, as the old legends suggested.

The records strongly support the notion that Singapore was a political center in the 1300s, but its real power and fame was due to its role as a port. Fourteenth century Singapore seems to fit at least in part the definition of a port of trade in which trade is less a function of the economy and more a function of government policy; thus trading would have been highly structured and institutionalized, with government agents playing key roles in port activities. Reports from Portuguese traders, in particular, suggest that Singapore operated in such a manner. Traders’ reports from various countries also indicate that Singapore was a point of exchange, rather than a source for goods. Local products were limited in type and were widely regarded to be of low quality. Chinese traders reported that there were few agricultural products due to poor soil. Local trade items were tin, hornbill casques (an ivory-like part of the hornbill bird, which was valued for carved ornaments), some wooden items, and cotton. Commonly traded products included a variety of fabrics (cottons and satins), iron rods, iron pots, and porcelains. The increase in activities by Chinese traders seems especially significant for Singapore and its trade. Various traders reported that, by this time, there was a permanent Chinese settlement in Singapore living peaceably with the indigenous population. This could have made the port especially comfortable and desirable for Chinese traders. Still, it is also clear from the reports of traders that pirate activities once again threatened ships. One of the best-known commentators of the time was Chinese merchant Wang Dayuan, who described the risks,

When junks [Chinese boats] sail to the Western Ocean the local barbarians allow them to pass unmolested but when on their return the junks reach Ji-li-men [an island in the mouth of the Melaka Strait], the sailors prepare their armour and padded screens as a protection against arrows for, of a certainty, some two or three hundred pirate prahus [small boats] will put out to attack them for several days. Sometimes [the junks] are fortunate enough to escape with a favouring wind; otherwise the crews are butchered and the merchandise made off with in quick time.

An early nineteenth century Malay author, Abdullah Munshi, indicated that the lore of Singaporean pirates was still strongly present at that time. He gave a grisly description of pirate activities, indicating that once a ship was taken, the pirates would bring it back to Singapore where they would kill the crew and either divide the spoils among themselves or fight each other to the death to gain the spoils. The description continues to describe the shores of what is now Sentosa Island as having “hundreds of human skulls rolling about on the sand; some old, some new, others with hair sticking to them, some with the teeth filed and others without.” While the lore may have been enhanced by passing time, the similarities to Wang’s contemporaneous account corroborates Wang’s account of the brutality and butchery that could befall traders in Singapore’s waters where the locals were, in Wang’s words, “addicted to piracy.”

While there were clear descriptions of the risks of trading in Singapore, it is nevertheless noteworthy the frequency with which traders of the time referred to Temasek in their writings. Wang’s descriptions were of the area called the Dragon’s Tooth Strait, thought by some scholars to refer to rock formations that, prior to their destruction, sat at the western entrance of what is today known as Keppel Harbour. Other scholars speculate that the Dragon’s Tooth Strait was what is now known as the Singapore Main Strait, about 10 miles south of Singapore. Either way, evidence indicates that this area was in the immediate vicinity of Singapore and that fourteenth-century references to the Dragon’s Tooth Strait referred to the port of Singapore. There was also a reference to Temasek in a memorial written in honor of a Vietnamese prince, who was said to be able to translate for Malay emissaries from Temasek. Further, a Javanese poem of the time also refers to Temasek. With such a variety of references to Temasek, ranging geographically from China to Vietnam to Java, it is clear that Singapore was known for its importance as a port well beyond vicinity of modern day Indonesia or Malaysia.

Scholars have found that Singapore’s rise as a trade-post developed concurrently with other major developments in world trade of the time. While China may have been feeling pressured by the power of the Mongol Empire, elsewhere the power of the Mongols was having a broader positive effect. Called the Pax Mongolica or Mongolian Peace, the Mongol influence over both the overland and maritime Silk Roads provided a context in which a new global trading system could develop. Previously, shipping occurred on long-distance routes from the Far East to India or even further west to the Arabian Peninsula, which was relatively costly, risky, and time-consuming. However, the new trading system involved the division of the Maritime Silk Road into three segments: an Indian Ocean sector linking the Gulf of Aden and the Strait of Hormuz-based Arab traders to India, a Bay of Bengal sector linking the Indian ports with the Strait of Melaka and its associated ports (including Singapore), and a South China Sea sector linking Southeast Asia with southern China.

Much of this shift in trade patterns came about through the development of an Islamic-based institutional structure developed by Arab traders who began trading on the Maritime Silk Road as early as the seventh century. This institutional structure provided a system for raising capital, establishing credit, transporting and storing goods, resolving disputes, and providing information about supply and demand and other factors that would promote trade. The formalized structure assisted with the development of trust and confidence that obligations would be met by trading partners. This trust permitted the subdivision of the trade route, creating interdependence among traders. The gradual expansion of Islam that in part accompanied this trade also facilitated the adoption of this Islamic trading system. The Islamic, north-India-based Mughal Empire left its mark on the Indian Subcontinent and Islam spread to Southeast Asia as well, with majority Islamic populations still seen today in Malaysia and Indonesia. Singapore’s growth as a significant port occurred at the time of this shift in global trading norms. Instead of one group of traders attempting to cover the entire Maritime Silk Road, more exchange happened with different trade groups covering different segments of the route. While the Islamic trading system seems to have been of fundamental global importance, it should be noted that the commonalities of Buddhism provided similar benefits of trust and confidence to other traders. The Srivijayan Empire was, in fact, a major Buddhist center and this seems to have assisted with Singapore’s eventual ascent to prominence due to its founder coming from the Srivijayan center of Palembang.

This era of Singapore’s history lasted through five rulers, according to the Malay Annals, or a period of about 100 years. However, while Singapore clearly prospered in its role as a port, this period of growth and rise to prominence was not untroubled. There were several larger, expansionist kingdoms in the region that prompted early Singaporeans to exercise awareness and caution. One of these, posing a threat from the north, was a Thai kingdom. The other, pressing from the south, was the Majapahit Empire based in Java. These concerns may have motivated Singaporeans to construct the previously mentioned fortification wall, indicating Singapore’s promise and prominence. The precise relationship between Singapore and these two regional powers is unclear, but there are suggestions of Singapore having the status of vassal state to both the Majapahit Empire and the Thai kingdom.

The Malay Annals contain a legend of a Majapahit siege that was perhaps provoked by a Singaporean ruler not providing the proper respect and tributes that would have been due the overlord of a vassal state. At the time, Singapore’s defenses included not only the fortified earthen wall but also a stockade-type structure made of wood. The Singaporeans withstood this initial Majapahit attack, but that did not remain the case.

There are a wider range of sources detailing accounts of a second Majapahit attack on Singapore, although the accounts vary somewhat. The Malay Annals indicate that Sri Sultan Iksander Shah, the fourth son of Sang Nila Utama and the fifth ruler of Singapore, had heard unpleasant rumors about his mistress, so he shamed her publicly. Her father, a treasury officer, was enraged by the public shaming and for revenge betrayed the ruler to the Majapahit by leaving open a gate to the fortified city. This enabled a subsequent Majapahit attack, with allegedly thousands of Majapahit landing on the beaches and storming the city once the gate was opened. While dates are uncertain, there are indications that this occurred in 1378. Some Singaporeans may have fled into the jungle, surviving the Majapahit attack and trying to rebuild afterward. However, these efforts, according to some accounts, came to nothing due to a threat from the Thai kingdom to the north. The Thais allegedly attacked and left the city a dependency until invading again in 1391, killing the ruler they had earlier put in place and completely destroying the city. Another account, written by the son of a Portuguese viceroy who led conquests in the region in the early 1500s, reported that the fifth ruler of Singapore was a usurper from Palembang named Parmeswara, who came to Singapore and shortly thereafter killed his host, the fourth ruler, and became the ruler for eight years. The brother of the assassinated leader was the ruler of Patani, part of an island southeast of the Philippines. He drove out Parmeswara with the support of the local people who never offered their trust or loyalty to the man who assumed power by murdering their leader. Another account by European colonists was very similar and written about the same time, but indicated that Parmeswara was driven out by the king of Siam (Thailand), who was the father-in-law of the murdered king of Singapore. Yet another account by colonial writers suggests that Singapore was under the authority of the Kingdom of Pahang on the Malay Peninsula, whose leader was a relative of the Singapore harbor master. Parmeswara killed the harbor master, provoking an assault on Singapore. Yet another colonial writer offered an account mirroring that of the Malay Annals. A final account indicates that Parmeswara was expelled from Palembang for some reason and then spent the next six years, from 1391 or 1392 to 1397 or 1398, ruling Singapore. While the details of the events cannot be known with certainty, it seems likely that Singapore was a vassal state of either the Majapahit or Thailand or perhaps both at different times. In addition to the more widely reported Majapahit attack on Singapore, the Chinese merchant Wang also reported an unsuccessful attack by Thai armies in the mid- to late 1340s. Further, while the accounts of that fifth ruler’s ascension to the throne and the sources of conflict within his reign vary, there is a reasonable amount of consensus that at the end of his ruling period of six to eight years, Parmeswara was either forced out of Singapore or was compelled to flee.

Kingdom of Melaka, 1398-1511

Parmeswara’s departure marks a significant change in Singapore’s fortunes and its future course. He did not flee and disappear into obscurity, though. Instead, he established a new kingdom slightly north of Singapore along the Melaka River (now western Malaysia) before he died in 1411. This Kingdom of Melaka became an important regional power and trade port, completely eclipsing Singapore and leaving Singapore to fade into relative obscurity, with only occasional mentions in the historical record after its decline.

While the Majapahit Empire seems to have conquered Singapore, its practice was not simply to take control of a territory and govern it as its own. Instead, the Majapahits raided a city, looted the wealth, enslaved the population, and burned any structures still standing. In this context, it is not surprising that Singapore did not exist as a port to rival Melaka once Parmeswara fled, as there was likely little remaining. The little that may have remained ultimately would have been under the authority of the Melakan ruler. A reference to Temasek in the writings of Chinese Admiral Zheng He notes his passage through the Dragon’s Tooth Strait in the early 1420s. Archeologists have also found shards of pottery from various parts of Southeast Asia, specifically Thailand, Myanmar, and Vietnam, that date from the century after Parmeswara’s flight. Such items indicate human activities near the mouth of the Singapore River but not on the royal ground of Fort Canning Hill, providing further evidence that Singapore was not completely abandoned after the elites left and that trade activities were ongoing, if less prominent. Similar evidence from later centuries is also present along the Kallang Estuary, not too far from the Singapore River. Thus, after the departure of Parmeswara, there was a serious decline in the political and economic stature of Singapore, but not a complete abandonment of this once-significant port.

The subsequent years saw an increase in piracy in the area, and it seems the leader of Melaka was able to establish the city as an important port because he offered protection from the pirates and a convenient location in the Strait of Melaka to provision ships. Chinese imperial records indicate that Parmeswara was a prominent leader. A Chinese delegation was sent to Melaka as early as 1401; and in 1405, Parmeswara returned to China with the delegation, was presented at court, and sought and received diplomatic recognition from China. He also offered Melaka as a base for China’s fleets under Admiral Zheng He. This connection with China provided Melaka with certain benefits, including patronage from China and a measure of protection that would be associated with such patronage. Anyone seeking to interfere with Melaka’s trade would know that he was also interfering with the interests of a much larger power, China. Parmeswara’s successor, perhaps strategically, converted to Islam, which included Melaka in the Islamic trading system, making this a desirable port of call to still more traders. This connection to the Islamic traders who dominated the Maritime Silk Road was important to Melaka because it was this trading network that met European demand for Asian products. Wealth followed, as Melakan rulers insisted that ships call at the port. To better control shipping in the Strait, leading both to greater security for the shipping and increased wealth, the Melakan rulers expanded their territorial control from the eastern side of the Strait (the Malay Peninsula) to the western side of the Strait (the island of Sumatra) and increased their naval power by tapping into the traditional alliances like that with the Orang Laut. However, this new power center proved to be relatively short-lived due to external challenges of a fundamentally different nature that would also change the fate of Singapore and the region.

Rather than facing regional challenges, the European colonial powers made their presence felt in Southeast Asia, first the Portuguese, then the Dutch, and finally the English. In 1488, Portuguese seafarer Bartolomeu Diaz was the first European to encounter southern Africa’s Cape of Good Hope. In 1497, fellow Portuguese explorer, Vasco de Gama built on Diaz’s success and sailed around the Cape of Good Hope, demonstrating to Europeans that India and access to the trade riches that lay beyond it could be reached by circumnavigating Africa. This opened the door for a flood of European traders seeking the wealth via the Maritime Silk Road. In 1502, Portuguese Admiral Alfonso de Albuquerque set sail for India. He was appointed viceroy of the Portuguese Indies and went on to capture the Indian city of Goa, making it the capital of Portugal’s eastern interests. From Goa, he traveled further east for more conquest. By 1511, he had set his sights on Melaka because of its significance as a regional trading center. The Portuguese fleet was well-armed; the Melakans were not. The battle for Melaka reportedly lasted for days, but while the Melakans possessed a few fire arms, they mostly relied on bows and arrows, spears, and other primitive weapons, whereas the Portuguese had heavy arms and armor. The Portuguese took control of the Strait and the port city and built a stone fortress to protect their interests. Like the Melakan rulers, they charged duties for passing through the Strait, which they controlled for the next 100 years.

Kingdom of Johor, 1511-1699

The defeated Melakan sultan, Mahmud, decided to reestablish a settlement in a different location and selected a place on the Johor River, which flows in to the Johor Strait, the small body of water separating Singapore from peninsular Malaysia. He then moved his capital to the island of Bintan, just to the southeast of Singapore and the Malay Peninsula in what is today Indonesia, but this settlement was attacked repeatedly by the Portuguese and ultimately destroyed in 1526. However, Bintan was significant because it provided a connection to the historical source of noble authority from Queen Sakidar Shah and the founding of Singapore by Sang Nila Utama. Since the Portuguese made a successful settlement at Bintan impossible, Sultan Mahmud relocated again, to Kampar on the island of Sumatra, where he died two years later. His successor, Ala-ud-din, attempted to establish his administrative capital on the Johor River and built a protective fort a few miles downstream. The following decades saw repeated battles with the Portuguese, which the Johor forces repulsed with some success, although Ala-ud-din eventually made a peace agreement with the Portuguese. Despite the defeat to the Portuguese and the repeated relocations of the capital shortly thereafter, Johor became an important actor in the region.

The primary power shifted from Melaka to Johor, but Singapore still merited mention in the writings of maritime traders of the time. Johor is in the immediate vicinity of Singapore but far enough away to offer different port opportunities. There are reports that, following the defeat of Melaka by the Portuguese, a Melakan admiral established operations in Singapore. Tomé Pires, a Portuguese trader and author of Suma Oriental, a primary source about the maritime trade routes of the time, reported in 1515 that the inhabitants of the Singapore channel area lived in a few unimportant villages. He referred to Singapore as a “kingdom,” but one with very little territory. Pires also noted that Chinese merchants still called at Singapore, a fact supported by archeological findings of sixteenth century Chinese porcelain fragments around the Kallang Estuary, reflecting activity in Singapore in a different location from the earlier trading venue. Another Portuguese writer, Joe de Lisboa, reported in 1526 that a town in Singapore had been destroyed by the Portuguese. Reports from the late 1500s continue to mention Singapore, as well, and both Portuguese and Dutch documents from the early 1600s mention the presence of a harbor master, which is a person of great significance in the Malay royal establishment. The harbor master would not only collect taxes from foreign merchant ships entering the harbor but also control most other aspects of harbor life, such as transporting and warehousing goods and deciding where foreign merchants could live. The fact that Singapore had a harbor master at this time indicates that it was still an active port for international shipping. Thus, as global shipping and trade entered a different phase with the emergence of important European powers in the region, Singapore continued to be tied to the trade networks that comprised the globalization of that age.

Regional conflict came to the fore again, as relative shifts in power among groups led to strained relations. Officials from Portugal and Johor had established a working relationship but toward the middle of the 1500s, Aceh, a Sumatra-based kingdom, was an ascendant and expansionist power. Given its location at the northern end of the Strait of Melaka, tensions with the Portuguese over control of shipping increased, as did tensions with Johor over rival claims to be the legitimate successors to the Srivijayan Empire. The tensions culminated in a naval battle between the Portuguese and Acehnese in 1577 just off the coast of Changi, Singapore. The Johor-Portuguese cooperation broke down in the 1580s over trade-related disagreements, and Johor besieged Portuguese-controlled Melaka in 1586–1587. In the context of these strained relations, Johor was attacked in the mid- to late sixteenth century and into the seventeenth century by both the Portuguese and the Acehnese, including the burning of Singapore in 1613 by the Portuguese, since Singapore was connected to Johor through its Melakan heritage and Singaporean heritage before Melaka. As an indicator of shifting alliances, Johor and Aceh teamed up in 1616 to attack Portuguese-controlled Melaka, but to no avail. The Johor sultans, being flexible, were often willing to simply move to a different location along the Johor River and continue their trading operations, thus maintaining an advantage over Aceh, allowing Johor to thrive despite greater rivalries.

Around this same time, in the early 1600s, the region experienced yet another significant shift in power as the Dutch became active in challenging the Portuguese monopoly on trade to Europe along the Maritime Silk Road. The primary rivalry between the Portuguese and the Dutch sometimes played out in direct conflicts, such as in 1603 when they fought a battle in the Singapore Strait or as in 1611 when the Portuguese complained that the Dutch were building a fort in the Singapore Strait area. However, given the importance of indigenous regional power centers, such as Johor and Aceh, the Portuguese-Dutch rivalry spilled over and touched these regional powers, alliances, and rivalries. The Dutch entered the area in the context of the Dutch East India Company, which was a joint-stock company, a professionally-managed corporation with shareholders who were part owners and could buy and sell their stocks. The company was incorporated in 1602 and was unique in the powers it had been granted by the Dutch government. It could negotiate on behalf of the state, and enter into contracts, treaties, and alliances; it could take over territories, build forts in the territories it controlled, appoint governors for those territories, raise an army, and even mint its own coins. It is likened to a state within a state, since it was the Dutch government granting such extensive authority. Between selling shares of the company and the ability to issue short- and long-term bonds to raise capital, the Dutch East India Company (DEIC) had substantial wealth. This wealth, coupled with aggressiveness, led it to amass enormous economic and political power. From 1602 to 1696, the dividends it paid its shareholders ranged from a low of 12 percent to a high of 63 percent.5 Its charter was renewed by the government every 20 years in exchange for financial compensation. The DEIC propelled the Netherlands to a position as a leading global trading power in the seventeenth century.

Initially, the Dutch were a useful ally for Johor. In 1603, they launched a joint assault on a Portuguese merchant ship off the coast of Singapore. The Portuguese continued to launch assaults on Johor’s ever-moving capital and also blockaded the Johor River. Johor’s trade was harmed badly, and they turned to the Dutch for assistance. The Dutch fought a naval battle with the Portuguese that ended the blockade and formed the foundation for a closer alliance between Johor and the DEIC.

However, while the Dutch may not have been concerned about challenging the trading power of Johor, they were very concerned about the power of the Portuguese. In a letter to the directors of the United Amsterdam Company, a branch of the DEIC, company representative Jacob van Heemskerck described interactions with the king of Johor and the assault on the Portuguese merchant ship. He also discussed how important and profitable the trade with China was to the Portuguese. He urged the company to send good ships so that they could attempt to break the Portuguese monopoly and enter into this lucrative Chinese trade themselves. The letter strategically analyzed different options for setting up a trade center, and Johor was near the top of the list behind Melaka. Heemskerck considered Melaka to be more desirable because of its defenses. The Portuguese elite were already living in stone houses and there was a stone wall protecting the town. These fortifications would allow the Dutch to better protect the wealth of the DEIC from hazards like fire or enemy assault. If they could not gain control of Melaka, then Johor was the next best choice, weaker in fortification but equal in strategic location. Heemskerck further argued that if the Company could gain control of textile trade at Johor, then Melaka could be effectively besieged. Moreover, the Portuguese would not dare sail to China with the DEIC’s ships at the mouth of the Johor River, and the DEIC would be able to take control of trade with China and Japan. These lofty ambitions to assert Dutch strength and to transform the existing trading patterns highlights the prominence that the Singapore region had in the global trade network of the time—the region was a linchpin of power in global trade.

Subsequent developments for the Dutch cast fortune on Johor, although it may not initially have been apparent. In 1612, the Dutch captured control of Jakarta, then known as Batavia, on the north end of the island of Java, with access to the Strait of Sunda that runs between the islands of Sumatra and Java. While farther from Indian trade routes than the Strait of Melaka, the Strait of Sunda offered a slightly shorter route to the Cape of Good Hope and around the southern part of Africa, thus being a preferable route for trade directly from Indonesia, in particular the trade of spices from the Moluccas (formerly the Spice Islands) to Europe or the Spice Route. The DEIC established its headquarters there, and it became the center for what would become the Dutch trading empire in Southeast Asia. This lessened the importance of the Strait of Melaka for Dutch trading and kept their attention focused well to the southwest of the Johor-Singapore-Melaka area.

While the territory around the Strait of Melaka was no longer of critical import, weakening the Portuguese hold on trade in East and Southeast Asia remained a top priority for the Dutch. The less trade that was controlled by Portugal, the greater the wealth that could be amassed by the DEIC. In 1640–1641, Johor joined the Dutch in besieging Melaka, and this time they succeeded. The Portuguese were driven from Southeast Asia. At about the same time, Acehnese power was also in decline following the death of their leader. The Portuguese and Acehnese were out of the way; and while the Dutch still controlled Melaka, they primarily focused on their regional headquarters at Jakarta (formerly Batavia), 500 miles to the south. This left an opening for Johor to exert its power in the area around Singapore.

Despite peaceful coexistence with the new European power, regional rivalries would rise again. Jambi, another Malay kingdom based on the island of Sumatra, challenged Johor’s power and status as a trading center and sacked the Johor capital in 1673. Johor regrouped, revenged itself on Jambi, and reasserted its strength as a meaningful port in the international trading system. The Dutch, still preoccupied to the south, paid little attention and observed from afar.

Kingdom of Johor-Riau and the Bugis Years, 1699-1818

Johor’s reemergence following the Jambi attack was short-lived. This time, the problems that arose were internal, and they brought the ancient Palembang-Singapore-Melaka-Johor ruling line to an end. People in territories controlled by Johor were unhappy with the domineering role played by Johor and its ruling sultan, Mahmud. Both local and European reports from the time mentioned various sadistic acts that Mahmud committed against the people of Johor. In 1699, Mahmud was assassinated by his own ruling council, which not only upset the line of succession since the sultan had no direct heir but also rattled traditional loyalties that had provided some stability to the Johor sultanate.

The Orang Laut, who had been loyal to the royal line throughout all of its changes of leader and location, were an important part of the power structure of Johor and had at times across the centuries proved a key force in the defenses of the sultanate. The ties had been based heavily on personal loyalty to the sultan. There was a strong patronage-based relationship in which the Orang Laut, in exchange for loyalty, strength, stability, and esteem, were rewarded with wealth and inclusion. The new line of leaders came from non-royal chief ministers, the first being Abdul Jalil. The Orang Laut transferred some of their loyalties to the new leadership but never to the same degree as they had to the royal line with its semi-divine origins. This compromised the established power structure and undermined long-term stability.

The next major change that came about after the death of the sultan was the rise of a new regional power. The Bugis people arrived as immigrants from Sulawesi (formerly Celebes), an island east of Borneo in today’s Indonesia. The Bugis were mercenaries who worked for various sultans on the Malay Peninsula. However, with time, they gained considerable power and became highly influential in the leadership of various kingdoms, including Johor. The rise of the Bugis was so significant that the 1700s are considered the century of the Bugis in Malay history. For the internally weakened Johor government, the increasing influence of the Bugis further disrupted previous power structures and undermined stability.

Another power shift occurred when, in 1717, Raja Kecik from Siak, a Sumatran area of the Melaka-Johor sultanate’s holdings, arrived and bluffed his way onto the throne. The people, seemingly thinking he could be a countervailing force to the rising power of the Bugis, played along. He was backed by a Sumatran ruler and arrived in the Johor capital, then in the Riau Islands, southeast of Singapore, in 1718 with a large Sumatran military force. The Orang Laut sided with this new leader, too, and for a time he was able to take power. Before long, though, the Bugis asserted their power and removed him from the throne. The Bugis then became the de facto rulers of Johor, adopting the title of “junior king” for their leader of Johor, relative to the name for the Malay leader, “great king.” With this the Johor sultanate took on a hybridized Malay-Bugis identity, leading to complexities that ultimately made the leadership vulnerable to the manipulations of European colonial powers.

After being dethroned, Kecik returned to Siak and established a Malay sultanate and set out to challenge Bugis domination of shipping in the Melaka-Singapore-Riau area with raids on shipping and occasionally full battles. The conflict also broadened to involve the Dutch, who were still formally in control of Melaka, despite their greater degree of activity based around Jakarta and the Strait of Sunda. There was also a significant degree of internal conflict facing Johor, again increasing instability in the sultanate. Sultan Suleiman, a puppet of the Bugis, desired more independence and, in 1755, made an agreement with the Dutch to help him gain greater autonomy and control over territory. The Bugis retaliated by attacking Dutch Melaka, a failed effort; then the Dutch retaliated by attacking the Bugis at the island of Lingga, south of the Riau Islands and Singapore. The Bugis-Dutch conflict went on for several years until the Bugis were defeated and a peace agreement was signed in 1758. This also resulted in an agreement to give Dutch exclusive tin rights, something Suleiman had initially granted the Dutch in return for their assistance. The following year there was a Bugis coup, placing Daeng Kamboja in power. However, instability continued after Sultan Suleiman died in 1760. The Bugis killed the sultan’s successor and took back control of the Johor Sultanate. The Bugis-Siak rivalry rose to the fore again when Raja Ismail of Siak fought a naval battle with Bugis forces from Johor-Riau led by Daeng Kamboja. This well-documented battle took place on the Singapore River in 1767. Archeological evidence, specifically coins of the Dutch East India Company dating 1730–1796, has been found near the mouth of the Singapore and indicates that Singapore continued to be an active port through this time.

The tumultuous relations continued between the three power rivals (Johor, Siak, and the Dutch) for some years, and instability within Bugis Johor was likewise ongoing. The peace agreement between Johor and the Bugis collapsed in 1782 when the Bugis began raiding Dutch possessions in the Strait of Melaka. The Dutch retaliated by destroying the raiding Bugis ships and then driving the Bugis out of Riau, the governing headquarters of Johor. The Dutch demanded the Bugis leadership acknowledge formally via a treaty that Johor-Riau was a Dutch port and the kingdom a Dutch holding. The Dutch also demanded agreement for a Dutch governor and garrison to be stationed at Riau. Thus, for the first time, there was formal European control of the successor sultanate to the Singapore-Melaka-Johor line. The Bugis tried again in 1785, one year after the treaty was signed, to win back Johor, but they failed. Bugis Sultan Mahmud’s next attempt to broaden the conflict was in 1787. He sought regional support by appealing for help to Sultan Illanun of Borneo to oust the Dutch. The Bornean forces succeeded in capturing Riau but held it for themselves until the Dutch quickly regained control, while Sultan Mahmud fled.

The various changes of authority created a much less stable sultanate than had previously existed when Singapore, Melaka, and Johor were able to fend off challenges, sometimes through strategic relocations, but they remained active and relatively prosperous powers in the ever-changing global system of trade. The internal divisions, challenges for authority, and competing claims of legitimate rule that troubled the sultanate under Bugis control set a foundation for the full colonization of the area with the arrival of yet another influential European actor: the English East India Company.

The English East India Company (EEIC) was also a joint-stock company, modeled on the Dutch East India Company. Queen Elizabeth I granted the charter on December 31, 1600, giving the company exclusive trading rights in the Indies as long as it did not challenge the established trading rights of “any Christian prince.” King James I granted the company a perpetual charter a few years later in 1609. Through the eighteenth century, the English were most interested in trade with India and concentrated their efforts most fully there, although certainly not exclusively. EEIC Captain Hamilton provided an account of his meeting in 1703 with Johor Sultan Abdul Jalil while en route to China. He reported,

[The sultan] treated me very kindly, and made me a present of the Island of Singapura, but I told him it could be of no use to a private person tho’ [sic] a proper Place for a Company to settle a Colony on, lying in the Center of Trade, and being accommodated with good Rivers and safe Harbours, so conveniently situated, that all the Winds served Shipping both go out and come into these rivers.

Hamilton also visited the island and gave it close inspection, as he gave descriptions of its soil, timber, and sugar cane. While no one knows for certain why the Johor leader would have offered the English such real estate (perhaps seeking an ally in the tumultuous situation that was developing with the Bugis and Dutch), it is certainly noteworthy that the English had the opportunity to gain the island much earlier than the establishment of their colony of Singapore and turned it down.

The EEIC’s initial forays into Southeast Asia took place after the founding of the company, but its successes were extremely limited. It sought to gain trade in the region and on the Malay Peninsula in particular, but the Dutch were successful in combating the competition and closing down the British trading ports in Southeast Asia. The one exception was Bengkulu (formerly Bencoolen) on the southwest coast of Sumatra, although it was not considered an ideal location. The difficulties of establishing thriving trade in Southeast Asia led the EEIC to concentrate its efforts on India. However, the English were not by any means disinterested in trade with China, and as historical trade patterns have shown, easy access to ports in Southeast Asia greatly facilitated that trade. The importing of Chinese tea, for example, transformed English society, giving rise to the idea of teahouses and time spent talking over cups of tea. This practice became an institution; and to meet the rising demand of this fashionable activity, large amounts of tea had to be imported from China. This led to a serious imbalance of trade for England that needed remedy. In addition to helping introduce opium to China and establishing a monopoly for the Chinese opium trade, the English also took careful note of what products from Southeast Asia the Chinese regularly imported. These included edible birds nest, hornbill casques, pepper, tin, tortoise shell, beeswax, and other products. Despite the past focus on Indian trade, some in the EEIC came to see the greater desirability of controlling ports in Southeast Asia, and in 1786, the English successfully established a port operation to service their India-China trade at Penang on the Malay Peninsula.

Underscoring the international nature of the forces affecting Southeast Asia, it was political conflict in Europe that helped shift power toward the English in Southeast Asia. In Europe, Napoleon had taken control of France and was waging war to expand the French Empire. The Napoleonic Wars, a series of conflicts between France and an alliance of opponents, took place from 1792 to 1815 when Napoleon was defeated at the Battle of Waterloo. In the context of these conflicts, in 1795, Napoleon invaded and occupied the Netherlands and eventually made it a part of the French Empire. The English, concerned about the rising power of France and a part of the allied opposition to counter it, were worried about the possible implications of French control of the Netherlands on their Asian trade. The English government ordered the English East India Company to take over temporarily some of the holdings of the Dutch East India Company, with the holdings to be returned at the end of the conflict; Melaka was taken over in 1795 and Jakarta in 1803. However, once it came time to return control, the Dutch East India Company had ceased to exist and it was the representatives of the Dutch government who returned for their holdings.

Having had control of the region, it was distasteful to some in the English East India Company to lose ground again to the Dutch. They saw it as perilous for their trade with China, particularly if the Dutch reasserted their authority in the Strait of Melaka to the Riau Archipelago area south of Singapore. However, the Governor-General of the EEIC, Francis Rawdon-Hastings, Earl of Moria and Marquess of Hastings (Lord Hastings), was forbidden from acting because the English Crown feared war with the Dutch. With time, however, trade priorities changed the opinions of important people.

Singapore’s early history is a function of its geographic location and advantageous port features that made it a recurrent focal point for world trade. From the beginning of trade, when boats sailed the entire distance from China to the Middle East or India while needing ports of call for provisions, to the eventual segmentation of the Maritime Silk Road, where different traders would specialize in different segments of the road, needing ports to trade goods, to finally the arrival of the European colonial trading empires, Singapore’s location at the mouth of the Strait of Melaka made it desirable real estate. While its fortunes rose and fell and while it may have fallen into relative obscurity as a port, compared to Melaka, Johor, or Bintan Island, some trade activities continued, proving that Singapore was in its ancient history a notable port of call in the globalized trading and shipping networks of the time.