As China comes into greater conflict with the West, and the United States in particular, now is a good time to consider the long arc of this relationship. In the West, Chinese history is commonly framed as having begun with the first Opium War, giving the impression that European powers always had the upper hand. But from the first direct contact between East and West-the arrival of the Portuguese in south China in the early 16th century-the Chinese were dominant.

In 1517, they appeared near the famed trading haven of Guangzhou, strange and unruly barbarians in wooden sailing ships. The language they spoke was an unintelligible mystery, their eight vessels puny by the standards of Zheng He’s treasure junks, and their ultimate origins a bit hazy. But like all other seaborne ruffians, they wanted to trade for the rich silks and the other wonders of China. The Chinese came to call them folangji, a generic term used at the time to refer to Europeans. More specifically, they were the Portuguese, and they were the first Europeans to sail all the way to China.

The adventurous mariners from the kingdom of Portugal had burst into the Indian Ocean in 1498, when Vasco da Gama rounded the cape of Africa and found his way to the southwestern coast of India. It was an Earth-rattling moment. Until then, Western Europe had been on the fringes of a global economy driven primarily by exchanges among China, India, and the Islamic world. Portugal was on the fringe of that fringe. All that would change. The arrival of the Portuguese in Asia heralded the coming ascendancy of the “West”-Europe, and later, America.

The Portuguese incursion was an equally crucial turning point in the Chinese history of the world. In fact, it would alter the course of China’s history more drastically than anything that came before, with the possible exception of the original Qin unification in 221 b.c. It was one of those rare moments in time when two historical narratives that had been meandering along quite separately suddenly came crashing into each other. They quickly became entangled, and would never again be unwound.

The Chinese couldn’t have known any of this in 1517. To them, the Portuguese seemed just like any other trade-hungry barbarians who had ventured to China by boat, horse, and camel over many centuries-whether Sogdian, Indian, Persian, or Japanese.

The Portuguese brought from Europe very different notions of trade and diplomacy than the Chinese had encountered before. More than that, though, the Portuguese were carrying on their wooden caravels an entirely unfamiliar culture from those the Chinese had previously met. Unlike the usual barbarians, who tended to adopt, at least in part, Chinese cultural practices, or participate in the rules and norms of the Chinese world order, the Portuguese and the Europeans who followed them to Asia thought their own civilization was superior. A clash was coming between peoples who each believed their civilization to be better than all others. The Chinese were simply unaccustomed to and unprepared for this sort of challenge from outsiders.

Foreign barbarians could defeat China militarily, and even overrun the empire, but, in Chinese eyes, the Mongols, Xiongnu, and other foreign pests never upset the Chinese self-perception of exceptionalism. Many of the supposed conquerors seemed more like the conquered. The Europeans, fully confident in the value of their own civilization, would present a wholly new threat to the Chinese world order.

There were already signs of what was to come from the earliest days of the Portuguese presence in Asia. When da Gama and his successors sailed into the Indian Ocean, they entered a world of well-established, multicultural trading networks and practices that had existed for eons. In the past, new entrants had simply joined the fray-including the Chinese. Zheng He, for example, wished to impress the world with Chinese power but didn’t seek to dominate the region and its trade. Wherever the Portuguese made landfall in Asia, the Chinese had already been. In southern India, da Gama was told tales of light-skinned, bearded men who had visited the coast generations earlier-references to Zheng He’s fleets, which had sunk their anchors off the coast almost a century prior.

The Portuguese, though, were bred amid the mercantilist brutality of Europe, where separation among trade, war, and power was barely perceptible. They intended not to simply participate in the trade between East and West, but to control it. And they used new, aggressive tactics and superior weaponry to impose their will. When they reached the flourishing entrepôt at Malacca in Southeast Asia, the Portuguese sought to conquer, which they did in 1511. The maritime states of South and East Asia had never seen anything quite like the Portuguese before. Bottled up by the paranoid Ming, the Chinese were not quite aware of who they were dealing with and what they were up to, either.

In the early 16th century, the Portuguese were about as much of a threat to the great Ming empire as gnats to an elephant. And at first, the Portuguese did little to challenge the Chinese system of trade. They sought relations with China very much like the standard seaborne barbarians who had been floating to Guangzhou for centuries. The 1517 mission carried Tomé Pires, a former pharmacist appointed by the Portuguese king as the country’s first official envoy to the Ming court. The Portuguese intended to become a vassal state of the Ming Son of Heaven and participate in tribute and trade like other barbarians, to gain access to lucrative Chinese goods. Their goal, in other words, was to join the Chinese world, not subvert it.

Things got off to a rocky start. The flotilla, under the command of Fernão Peres de Andrade, was denied access to Guangzhou by a local naval commander. The suspicious Ming were constricting foreign trade; Portugal was not a formal tributary state, and therefore was not recognized by the dynasty’s officials as having the right to trade. After a month of waiting, Andrade threatened to sail on anyway, and the nervous local commander relented. Once at Guangzhou, Andrade unwittingly alarmed the town’s fussy functionaries by firing his cannon in salute, a serious faux pas in Chinese protocol. The Ming authorities were no more amused by Portuguese boasting about deposing Malacca’s king, a longtime loyal Chinese vassal. Fortunately, the honest and diplomatic Andrade smoothed matters over, and soon the two parties were exchanging pleasantries.

The Portuguese were dazzled by what they found in Guangzhou. Its incredible wealth far surpassed anything back home. One contemporary Portuguese account records their wonderment at a lavish ceremony to welcome a governor returning to the city. “The ramparts were covered in silken banners, while on the towers reared flagstaffs from which also hung silken flags, so huge that they could be used as sails,” it reads. “Such is the wealth of that country, such is its vast supply of silk, that they squander gold leaf and silk on these flags where we use cheap colors and coarse linen cloth.”

Andrade had arrived at an auspicious moment, when the emperor, Zhengde, was less hostile to foreigners and international exchanges than most of his Ming predecessors. Chinese officials in Guangzhou agreed to accept Pires and his retinue, to await permission to visit the emperor. When Andrade departed in 1518, he left relations with China on a solid footing. “Andrade had arranged matters in the city of [Guangzhou] and the country of China so smoothly that, after he had left, commerce between Portuguese and Chinese was conducted in peace and safety, and men made great profits,” one Portuguese scribe recorded. Not for long.

Portuguese bellicosity quickly undid Andrade’s good work. His brother, Simão de Andrade, arrived on the China coast from Malacca in 1519, but this Andrade was a significantly different personality-“pompous, arrogant and spendthrift” by one account. He almost instantly alienated his hosts by building a fort on a Chinese island, forbidding other foreigners from trading ahead of him, and then abusing a Ming official who tried to assert control over the situation. By far the worst affront Simão committed was purchasing Chinese children, probably as servants. The Chinese, however, thought the Portuguese roasted the children for dinner, a claim that even made its way into the official history of the Ming dynasty: The Portuguese went “so far as to seize the children for food.” One Portuguese writer lamented that “within a few days their wretched behavior earned them the reputation not of friends and allies but of vile pirates and enemies.”

The reports of this atrocious behavior sent to Beijing doomed the already-troubled Pires mission. The Portuguese ambassador had made his way to the capital, where he awaited an audience with the emperor. The climate was somewhat hostile. Chinese officials sent memorials to the court condemning the Portuguese for their ill treatment of the king of Malacca and advocating that the emperor reject the Pires embassy. Making matters worse, Pires handed the court a letter from the Portuguese sovereign, King Manuel I, that the Chinese found impertinent. It was composed “in the manner he customarily adopted towards pagan princes,” according to a Portuguese description.

The death of the emperor in 1521 signaled the end of the mission. Pires was hustled out of Beijing the next day and sent back to Guangzhou. There he was forced to write to King Manuel of the emperor’s demand that the Portuguese restore the sultan of Malacca to his rightful throne, and Pires was held hostage for compliance. He would never leave China. Sometimes kept in harsh conditions and fettered, he died there in 1524.

The situation got uglier still when a new flotilla of Portuguese came to trade shortly after the emperor’s death. When news of his demise trickled in to Guangzhou, local officials ordered the Portuguese and all other foreign traders to depart. But the ornery Portuguese, already conducting business, refused. The Chinese assembled a sizable fleet and attacked the outnumbered Portuguese, sinking one of their vessels and taking prisoners. On two other occasions, Portuguese trading ships and Chinese war junks came to blows. Then, in 1522, another Portuguese squadron showed up off the Chinese coast with a commission to forge peaceful relations with the Ming. They blithely sailed into a Chinese onslaught that sank two of their three ships. The unfortunate Portuguese captured in these engagements endured a horrible end. “Twenty-three individuals were each hacked to pieces, losing their heads, legs and arms,” one surviving eyewitness recounted. “Their genitals were stuffed in their mouths, and the trunk of each body was wrapped around the belly in two chunks.”

The Portuguese were pushed to the shadows of the China trade. Barred from official exchange, they spent the next 30 years engaged in the illegal, but still vibrant, trade that evaded Ming control. Yet, eventually, they were brought in from the cold. The trade with Portugal proved too lucrative to ignore, and local Ming officials began to see the usefulness of these belligerent newcomers. In 1557, Ming mandarins in southern China allowed the Portuguese to settle in a trading colony on the peninsula of Macau, a short distance from Guangzhou. Within five years, a community of about 900 Portuguese had collected there, building two churches and some modest homes. As trade became more liberal, the colony flourished even more. To the Chinese, Macau became a truly foreign place, with strange architecture, stranger people, and unfamiliar religious processions. Some local Chinese saw the settlement in Macau as a bad omen; others complained that it was no longer part of China. One European noted in the 1580s that it was “the natural tendency of the Chinese to fear and to bear ill will towards foreigners.” They called the Portuguese “foreign devils.”

Odder than Macau itself, though, was that the colony existed at all. The settlement was clearly outside the usual rules of trade and diplomacy that governed the Chinese world. Portugal was not able to forge formal relations with the Ming court like other countries that traded with the empire. Macau survived because it profited local officials and merchants who possessed the authority and nerve to defy the central government. An official Ming history criticized one such independent-minded mandarin for “valuing the precious goods (of the Portuguese), pretending to forbid but secretly allowing the evil to continue to grow.”

From their inception, relations with the West ran by different rules. The Chinese, though, retained the upper hand. The Portuguese had some nifty military technology, most of all their highly effective cannon, which the Chinese duly noticed. But the handful of ships they were capable of deploying on the Chinese coast could not possibly challenge Ming supremacy. (In fact, the expert seafarers of Portugal learned a thing or two about shipbuilding from the Chinese, including the practice of waterproofing wooden hulls with a coating of bitumen.) And just in case these folangji got out of line, a wall and a gate were constructed across the narrow point of the Macau peninsula in 1573, and the Portuguese were forbidden to cross it. Significantly, little farmland was enclosed on the Macau side of the wall, which left the Portuguese dependent on the Chinese for food. The Ming could simply lock the gate and starve these barbarians into submission. Macau existed only at China’s pleasure.

Other gnats from the far-off “Western Ocean” were swatted just as effortlessly. The Spanish, led by Miguel López de Legazpi, sailed across the Pacific from Spain’s empire in the New World and took control of Manila in what became the Philippines. Almost immediately-in 1573-the first shipment of Chinese goods was dispatched from Manila to Acapulco in New Spain (now Mexico). The Spanish, like the Portuguese, tried to forge formal trading relations with the Ming but got nowhere. Nevertheless, Manila became a major hub of the China trade, and bulging Chinese junks brought prized porcelain and other products that then got shipped on to Mexico via Spanish galleons. Next came the Dutch. The first Dutch vessel appeared off the coast of Macau in 1601.

The Portuguese chased off the competition, but they were back soon enough-too soon, if you asked the Ming authorities.These hongmao, or “red hairs,” as the Chinese called them, earned a reputation even worse than the folangji. In 1622, the Dutch occupied islands off the Fujian coast, started constructing a fort, and dispatched an ultimatum to the Ming authorities: If they didn’t allow Chinese traders to conduct business with them, the Dutch would attack Chinese shipping and coastal towns. When they didn’t receive a satisfactory response, the Dutch plundered hamlets and burned Chinese junks around the city of Xiamen. That was too much for the Chinese, who assembled a naval squadron in early 1624 and attacked the Dutch position, eventually forcing them to evacuate.

Unable to gain a foothold on the Chinese coast, the Dutch instead settled on the island of Taiwan, where they erected a stout fortress called Casteel Zeelandia. Chinese junks sailed to this Dutch outpost to trade. It wasn’t the kind of trading relations the Dutch preferred, but it was all they had. These new barbarians, despite their persistence, were pushed to the margins of the Chinese world.