In the twenty-third year of the Jingyan era (1298), the strong monsoon winds billowed the massive sails of the Eastern Song merchant ships. Having seized control of the "New Jade Gate Pass" (Palembang), thus controlling the vital trade route between East and West, the merchants of the Eastern Song were no longer content with spices and pearls from the South Seas. They turned their gaze to the more distant and mysterious shores of the Indian Ocean. Fleets laden with silk, porcelain, and the finest spices sailed majestically through the strait, heading towards the legendary Indian subcontinent.

Before setting off, the merchants were calculating their gains meticulously, believing they could easily exchange their goods from the Eastern Song Dynasty for mountains of gold and silver, just as they had done when they conquered the Spice Islands. However, reality dealt them a harsh blow. The princes, nobles, and local officials of the Indian states were insatiably greedy, often resorting to extortion and plunder when faced with the Eastern Song merchants who had traveled from afar. Goods were seized, tariffs were doubled, and if they could not satisfy the bottomless appetite of the local officials, they would lose both their money and their people.

Merchants overseas, having suffered countless injustices, jointly petitioned the court to send troops to seek justice. However, this time the court's response was unusually lukewarm. The previous campaign against Srivijaya was because the court could directly profit from it and it was relatively close; but attacking the Indian states was a long and arduous journey with long supply lines, and apart from helping the merchants vent their anger, the court could hardly see any substantial benefits.

Although most wealthy merchants had powerful officials as their backers, these high-ranking officials were well aware that wealth acquired through power must ultimately serve that power. When the Eastern Song Dynasty first relocated to Luzon, everything was in ruins, and merchants relied on their connections with officials to borrow ships from the court to go to sea, thus accumulating their initial capital. Now, if a long-distance expedition were to be undertaken, the pros and cons had to be weighed—if the military expenditure far exceeded the gains, the officials who supported the expedition would certainly be impeached by their political enemies. At that point, not only would power be usurped, but the merchants' tributes would also vanish.

Moreover, although the Eastern Song Dynasty was lenient towards merchants, allowing their descendants to take the imperial examinations, the merchants themselves still could not enter officialdom, and their political status was ultimately limited. Most court officials reached a consensus: the court would not send troops, but it could not stand idly by and watch its people suffer humiliation. Thus, a peculiar imperial edict was issued—allowing merchants to form their own guard units and to purchase outdated weapons discarded by the army at low prices. At the same time, out of consideration for protecting the local population, the number of Song people in the guard units was limited, but there were no restrictions on recruiting natives.

As soon as the policy was announced, merchants heading to the Indian Ocean quickly banded together and formed the "Western Merchants Association." Members were required to pay 10% of their profits as a membership fee, and the association promised to protect the lives and property of its members with swift and decisive action. Soon, the association assembled a 1,000-strong Song Dynasty guard and recruited another 5,000 strong locals from Sumatra and New Kosari, forming an armed caravan of over 6,000 men, their sights set on the Kingdom of Kakatia, which had previously been the most ruthless in its extortion efforts.

This army was uniquely composed: a thousand Song guards, armed with muskets, served as the supervisory force and core striking power; five thousand natives, clad in simple rattan armor and wielding machetes and spears, acted as cannon fodder and vanguard. At this time, the Eastern Song dynasty's musket technology had undergone more than a decade of development, and the army had been equipped with advanced firearms resembling the prototype of matchlock guns. However, the muskets sold to merchants were the first-generation models—short range, slow rate of fire, and prone to barrel explosions. Even so, against the Kakatiya army, who didn't even know what gunpowder was, this was still a decisive victory.

The Western merchants promised the native soldiers that after the city fell, they would be allowed to plunder freely for three days, and they could keep 30% of all the spoils. With such a generous reward, the natives cheered and their eyes gleamed with greed, wishing they could immediately raze the enemy city to the ground.

The merchant guild's first target was the relatively weakly defended port of Nello, one of the main ports of the Kingdom of Kakatia. Local officials, engrossed in pleasure, were completely unprepared for a surprise attack from the sea. When the Western Merchant Guild's fleet appeared on the horizon, the port guards mistook it for an ordinary merchant ship. Five thousand native soldiers swarmed ashore like wolves and tigers, easily breaching the city gates.

The guild leader personally led his men into the government office, beheading the official who had most ruthlessly extorted him, using the head as a sacrifice. He then ordered the recovery of all the seized goods. Immediately afterward, the native army began looting like locusts, the city filled with cries of despair and flames soaring into the sky.

Three days later, the Western Merchants Association found a local who was fluent in both languages ​​in the ruins to act as an envoy. The envoy went to the capital, Varangar, to meet King Prataparudela II and lied that the Eastern Song Empire had sent troops to punish corrupt local officials.

King Pratapaludela II was furious upon hearing of the attack on the port. Regardless of the local officials, they were still his subjects, and how dare a group of merchants so defy royal authority! In his rage, he ordered the execution of the envoys and assembled an army to annihilate the arrogant caravan.

Having waited in vain for the envoy's return, the Western Merchants' Guild knew the negotiations had broken down. They acted decisively, boarding ships under cover of night and evacuating from the port of Nerol. This battle not only recouped the cost of building their army but also netted them a large profit, emboldening them further. Without hesitation, they turned and attacked Maslibadan, Kakatia's second largest port.

Using night raids and the threat of firearms, the Western Merchant Guild successfully captured Maslibadan. During this time, they discovered that the local Dalits (untouchables) were living in dire straits, suffering oppression from the higher castes and having no sense of belonging to the kingdom. The guild immediately extended an olive branch, using food and money as bait to quickly recruit 10,000 Dalits into their ranks.

Soon, King Plataparudela II assembled ten thousand elite soldiers and marched menacingly towards Maslibadan. The Western Merchants' Guild adopted a peculiar formation: ten thousand Dalits at the forefront. Although numerous, these men were poorly trained and equipped, and faced with the charge of the regular army, they quickly crumbled and scattered in all directions. The guild leader angrily cursed, "Truly a bunch of lowly commoners, utterly useless!"

However, the Dalits' defeat successfully slowed the enemy's advance. Taking advantage of this opportunity, the merchant guild dispatched 5,000 native soldiers to fight. These native soldiers, who had acquired a great deal of wealth through plunder in recent days, were highly motivated in battle. In addition, their weapons were superior to those of the Indian soldiers, and for a time they fought the Kakatiya regular army to a standstill, with neither side gaining a clear advantage.

Just as the two sides were locked in a stalemate, the Western Merchants' Guild revealed its trump card—a thousand Song Dynasty guards armed with muskets, who flanked the enemy lines and unleashed a volley of fire. "Bang! Bang! Bang!" The deafening explosions, accompanied by billowing smoke, instantly felled the Indian soldiers in the front ranks. The Kakatiya army, who had never seen firearms before, believed the caravan had used "witchcraft," and their morale plummeted.

Taking advantage of the enemy's confusion, the merchant guild's native army launched a charge. Caught in a pincer movement, the Kakatia army suffered a crushing defeat and fled. In this battle, the native army suffered more than half its casualties and was essentially rendered ineffective, but it also dealt a severe blow to King Plataparudela II.

After the crushing defeat, King Plataparudela II finally realized that this armed caravan was no ordinary bandit, but a formidable force with powerful firepower, and that a direct confrontation would only increase casualties. Therefore, he had no choice but to humble himself and send envoys to sue for peace. The Western Merchants' Guild, seeing an opportunity, also agreed to a deal: the Western Merchants' Guild would use a portion of its looted spoils to "lease" the port of Nellore from the kingdom.

When King Plataparudela II did the math, he discovered that the "rent" was actually much higher than the taxes previously paid by the port of Nerol. He couldn't help but berate the corrupt local officials: "These bastards, they've been skimming off my money layer by layer!"

With the port of Nerol, controlled by the Western Merchants Association, as their base, Eastern Song merchants thrived, continuously exporting large quantities of spices, silk, porcelain, and jewelry to various parts of Kakatiya. However, since India lacked the bulk commodities urgently needed by the Eastern Song, except for cotton and dyes, the merchants returned laden with the large amounts of gold, silver, and raw materials they had acquired through trade, setting sail eastward once again, thus beginning a new cycle of trade.

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