The Last Embassy: Macau’s Final Gamble in Nagasaki, 1640

Chapter One

The Arithmetic of Desperation

Macau in the spring of 1640 was a city running out of options and running out of time. The mathematics were brutal. The Portuguese enclave on the South China coast owed somewhere between 400,000 and 700,000 taels of silver to Japanese creditors, an extraordinary sum, accumulated over decades of a financial instrument called respondência that had kept the Macau-Nagasaki silk trade afloat even as everything else conspired to sink it. The creditors were powerful Japanese merchant families, the Suetsugu and Nakano clans of Hakata and Nagasaki, who had grown rich lending working capital to Portuguese traders and who now wanted their money back. The Manila trade with the Spanish had collapsed. The Chinese market was disintegrating as Manchu armies swept south. The Dutch, those tireless Protestant opportunists, were tightening their grip on the Strait of Malacca, choking Macau’s lifeline to Goa. And as of the previous year, the shogun of Japan had made it a capital offence for any Portuguese vessel to enter Japanese waters.

This was the situation in which the citizens of Macau gathered in the Senate House on 13 March 1640 and voted, unanimously, to send a diplomatic mission to Nagasaki.

The decision was not reckless. It was, by the logic of Macau’s situation, almost rational. The city had precisely two choices: send an embassy and hope the Japanese could be persuaded to reopen trade, or do nothing and watch the economy die. The debts alone would have been enough to concentrate the mind. Under the terms of respondência, a maritime credit system in which silver was borrowed against cargo rather than hull, the Japanese lenders bore the risk of shipwreck and piracy, but they charged accordingly: 25 to 35 per cent interest per voyage, climbing to 50 or even 80 per cent in bad years, with a 10 per cent penalty compounding for each year of delayed repayment. By 1640, the accumulated debt was a millstone around the neck of every merchant house in the city. If the Japanese could be persuaded to resume even limited commerce, the debts could be repaid and the colony might survive. If not, Macau faced bankruptcy in a world that had no bankruptcy courts.

So they voted to go. And they voted to go unarmed.

Chapter Two

The Men Who Volunteered to Die

The embassy that sailed from Macau on 22 June 1640 consisted of 74 men aboard a single galliot, not a grand carrack of the kind that had once hauled hundreds of tonnes of silk and silver between the two ports, but a modest vessel rigged with a straw sail, chosen precisely because it looked humble. The message was supposed to be unmistakable: this was not a trading voyage. This was not an attempt to sneak merchandise past the ban. This was diplomacy, bare-handed.

They carried no cargo. They brought 6,000 taels of silver for expenses, a pittance compared to the fortunes that had once changed hands on the Nagasaki waterfront, and nothing else of commercial value. The four ambassadors chosen to lead the mission were among the most senior and respected citizens Macau could offer: men whose age and standing were meant to signal gravity, sincerity, and the desperate earnestness of the city’s plea.

Luís Pais Pacheco was 68 years old, a widower born in Kochi on the Malabar Coast, who had served as Capitão-mór, of the Japan voyage in 1626 and knew the route and the protocols intimately. Rodrigo Sanchez de Paredes was 55, a native of Tomar married into Macanese society. Gonçalo Monteiro de Carvalho, 51, born in Mesão Frio, had served as a Senate counsellor and overseer of the Japan voyages. Simão Vaz de Paiva, 53, was Lisbon-born and Macau-married. The ship’s master was Manuel Álvares. Every one of these men knew what the 1639 edict said. They knew the penalty was death. Before embarking, all 74 confessed their sins and received communion. The city of Macau held daily services of intercession for their safe return.

These were not young adventurers seeking fortune. They were old men who had weighed the odds and concluded that the slim chance of reopening the trade was worth staking their lives on, or, perhaps more accurately, that the death of their city if they stayed home was worse than the probable death awaiting them in Nagasaki.

Chapter Three

A Century of Silver

To understand why 74 men would sail voluntarily into a harbour where they had been promised execution, you have to understand what had been lost, and how staggeringly much money was at stake.

The Macau-Nagasaki trade route was, for the better part of a century, one of the single most profitable commercial operations on Earth. Its foundation was an elegant arbitrage born of mutual prohibition: the Ming dynasty had banned direct trade with Japan, primarily to starve the wakō pirates raiding China’s coastline of their economic oxygen. Japan’s newly developed silver mines, above all, the prodigious Iwami Ginzan, were producing the metal in quantities that staggered contemporary observers. China, meanwhile, was transitioning to a silver-based economy and needed the stuff desperately. Japanese elites, for their part, craved high-quality Chinese silk with a passion that bordered on the irrational.

The Portuguese, established in Macau by 1557 and in Nagasaki by 1571, positioned themselves as the indispensable middlemen. They bought Chinese silk in Canton, loaded it aboard their carracks, sailed it to Nagasaki, and exchanged it for Japanese silver, which they then carried back to China to buy more silk. The profit margins were extraordinary. The Nau do Trato, the “Great Ship” that made the annual round voyage, was a floating treasury. Portuguese chroniclers reported that a single voyage could extract over 600,000 cruzados in silver, and that was probably a conservative figure.

Modern estimates of the silver flows are staggering. Between 1580 and 1600, the Portuguese shipped roughly twenty metric tonnes of Japanese silver into China every year. Between 1600 and 1615, the figure surged to somewhere between 150 and 200 metric tonnes annually. Over the full span of the trade, approximately 10,000 metric tonnes of Japanese silver reached China through Portuguese hands. Even in the final years, when the political situation had deteriorated to the point of open hostility, the volumes remained immense: in 1637, a fleet of six Portuguese galliots departed Nagasaki carrying 2,600 chests of silver valued at nearly seven million Dutch florins. The following year, another 2,350 chests.

These were numbers worth risking death for.

Chapter Four

The Squeeze

The trade’s profitability had always depended on the Portuguese occupying a monopoly position as intermediaries, and by the 1630s that monopoly was being crushed from every direction.

The Tokugawa shogunate had been tightening control over foreign commerce for years, driven by a conviction, not entirely unjustified, that Catholic missionaries and Portuguese merchants were two faces of the same coin. The Jesuits had never bothered to hide their financial dependence on the Macau-Nagasaki trade. They received an official allotment of silk under the pancada system, the fixed-price bulk purchasing cartel the shogunate had imposed to prevent the Portuguese from extracting excessive profits, and used the proceeds to fund their missionary operations. For the bakufu, the equation was straightforward: Portuguese ships meant Portuguese priests, Portuguese priests meant Christian converts, and Christian converts meant a potential fifth column loyal to a foreign spiritual authority.

The five sakoku edicts issued between 1633 and 1639 had progressively strangled Japanese engagement with the outside world. Japanese citizens were forbidden to travel abroad on pain of death. Foreign trade was restricted to Nagasaki. The Portuguese were confined to Dejima, a tiny artificial island in the harbour built specifically to quarantine and surveil them. And then, in 1639, the final edict expelled them altogether.

By 1640, the trap had closed. Macau had lost its monopoly, lost its access, and owed a fortune it could not repay. The embassy was a Hail Mary thrown by men who had no other play.

Chapter Five

Into the Harbour

The galliot arrived in Nagasaki harbour on 6 July 1640, two weeks after departing Macau. Whatever the ambassadors had expected, and they must have expected trouble, the reality was immediate and total.

A Japanese interpreter, a tsūji, met them at the harbour mouth. Guard boats surrounded the vessel before it had finished anchoring. The Japanese confiscated the ship’s rudder, sails, guns, and ammunition. The seventy-four men were forbidden to disembark freely and were confined under armed guard at Dejima, the same artificial island where Portuguese merchants had been penned before the final expulsion. Retainers of the local Ōmura lord provided the muscle. There was no ambiguity about the situation: the ambassadors were prisoners from the moment they arrived.

The local magistrate, the Nagasaki bugyō, Baba Saburōzaemon, interrogated the four ambassadors and had their petition forwarded to Edo, where the shogun Iemitsu and his senior council, the Rōjū, would decide their fate. The petition itself was straightforward: Macau wished to repay its debts and respectfully requested that trade be reopened. The ambassadors offered goodwill, contrition, and silver. They had, they believed, something the Japanese wanted, a settlement of the outstanding respondência obligations, and they hoped this would be enough to crack the door open, even slightly.

It was not enough. It was not close to enough. The petition was rejected out of hand.

Chapter Six

The Executioners Arrive

In Edo, the shogun’s council deliberated with the kind of efficiency that suggests the conclusion had been reached before the discussion began. Iemitsu had staked his authority on the sakoku edicts. The 1639 decree was not a suggestion. It was not a negotiating position. It was an absolute prohibition enforced by the threat of death, and any failure to carry out that threat would undermine the entire edifice of Tokugawa control over foreign affairs. The Portuguese had been told, in terms that admitted no ambiguity, that any ship arriving from Portugal or its territories would be burned and its crew executed. A ship had arrived from Portugal’s territories. The logic was unanswerable.

The council dispatched two special commissioners to Nagasaki: the chief inspector Kagatsume Tadasumi and the inspector Nonoyama Kanetsuna. They made the journey from Edo to Nagasaki in ten days, a remarkably rapid transit that underscored the urgency with which the shogunate approached the matter. They arrived late on the night of 1 August 1640.

They brought with them a retinue of executioners. The number of executioners was exactly equal to the number of Europeans in the embassy.

This was not an oversight. This was theatre. The Tokugawa state understood, perhaps better than any government, the political utility of spectacle, and the precise calibration of the executioners’ number, one blade for each man, was a statement of premeditation, finality, and administrative thoroughness. Nothing about what was to follow would be haphazard. Nothing would be improvised. The machinery of the state would function with the same meticulous order it applied to tax assessments and road maintenance.

Chapter Seven

Gala Dress

On the morning of 2 August, the Portuguese ambassadors were summoned to the magistrate’s audience chamber. They had spent nearly a month in confinement at Dejima, waiting for word from Edo, and the summons, the first official communication since their petition had been forwarded, was taken as a hopeful sign. Perhaps the shogun had relented. Perhaps the offer to repay the debts had found favour. Perhaps the door was opening.

The four ambassadors dressed in their finest gala clothing.

The chief commissioner addressed them as “villains” and read the imperial death sentence. The decree stated that they had been condemned for wilfully flouting the 1639 edict, which mandated the burning of the ship and the execution of the crew for any vessel arriving from Portugal or its territories. There would be no negotiation. There would be no reprieve. The sentence was death.

One imagines the ambassadors standing in their best silks, listening to words they almost certainly did not fully understand, the sentence was read in Japanese, while the interpreter translated and the full weight of their miscalculation settled over them like a physical thing. They had gambled that commerce was stronger than ideology. They had gambled that debt was a form of leverage. They had gambled that the shogunate, confronted with 74 unarmed old men bearing nothing but a petition and an apology, would see not a threat but an opportunity. They had been wrong about all of it.

Chapter Eight

Martyrs’ Mount

The executions took place on 3 August 1640, some accounts give 4 August, at Nishizaka hill, outside Nagasaki. The location was heavy with meaning. This was the same hill where 26 Christians had been crucified in 1597, the same hill where 55 had been burned and beheaded in the Great Martyrdom of 1622. The shogunate’s decision to carry out the sentence there was a deliberate act of historical layering: each new execution on the hill reinforced the accumulated message of all the previous ones.

61 of the 74 members of the embassy were beheaded. All four named ambassadors, Pacheco, Paredes, Carvalho, Paiva. The method was simultaneous beheading: swift, efficient, and administered with the impersonal precision for which Japanese executioners were justly renowned. Following the beheadings, the victims’ heads were placed on spikes and displayed as a public warning.

The shogunate was not interested in quiet disposal. It was interested in communication.

Chapter Nine

Thirteen Men in a Leaky Boat

Thirteen men survived the execution. This was not an act of mercy. It was, like everything else about the affair, an act of statecraft.

The shogunate had selected the thirteen with care. They were not chosen at random, nor were they spared because they were unimportant. They were chosen because they were useful. Manuel Fernandes was a sailor with piloting skills. Domingos de Quadros was a surgeon. João Delgado was a scribe. Manuel Cardoso was the leader of the sailors. The remaining nine were jurubaças, Luso-Asian interpreters of mixed heritage. These were men who could navigate a ship, treat the sick, write an official report, and communicate its contents in Portuguese. They were, in other words, the minimum viable crew for carrying a message home.

On 4 August, the thirteen survivors were brought to the harbour and forced to watch as the Japanese burned their ship. The galliot that had carried seventy-four men from Macau, the humble vessel with the straw sail, chosen to signal peaceful intent, was reduced to charcoal and ash while the men who had sailed it stood under guard and watched.

Then they were given the message.

The words attributed to Iemitsu’s decree constituted one of the most uncompromising pronouncements in the history of early modern diplomacy. The survivors were told to inform Macau, and through Macau, the world, that Japan’s doors were closed absolutely and permanently. Even if the King of Portugal himself came, or even God himself, the penalty would be the same.

The thirteen men were given a “licence for safe passage”, a document to protect them from Dutch or Chinese pirates, and placed in a small, barely seaworthy boat equipped with six pairs of oars. They departed Nagasaki on 1 September 1640. Somewhere between 2 and 20 September, they arrived back in Macau, alive and carrying the worst news the city had ever received.

Their testimonies were recorded by the Jesuit priest António Francisco Cardim. Among those who gave testimony was Miguel Carvalho, a 47 year-old sailor of Korean descent who had been born in Macau in 1593, a man whose very existence was a testament to the tangled, polyglot, multinational world the sakoku edicts were designed to destroy.

Chapter Ten

The World After

The execution of the 1640 embassy did not merely end Portuguese-Japanese relations. It punctuated them, a full stop applied with a blade to the neck of 61 men who had come, unarmed and in good faith, to settle a debt.

For Macau, the timing was catastrophic. In December 1640, just three months after the survivors limped back into port, Portugal revolted against the Spanish Habsburg monarchy and restored its own independent king. The ensuing war with Spain severed Macau’s trade with Manila, cutting the city off from New World silver at the precise moment it had lost access to Japanese silver. The following year, 1641, the Dutch captured the fortress of Malacca, severing Macau’s direct maritime link to Goa and the Estado da Índia. In the space of eighteen months, Macau lost its three principal trading partners, Japan, the Philippines, and Goa.

The city survived. Macau’s merchants pivoted to Southeast Asian markets, sandalwood from Timor, Solor, and Flores; pepper and silk from ports in Vietnam and Siam; a carrying trade in Chinese tea, porcelain, and silk destined for the Dutch in Batavia. By the late seventeenth century, Macau had reinvented itself as a leaner, humbler entrepôt, its fortunes tethered to a dozen minor trades rather than the single, glittering artery of the Japan route. The city would persist for another three and a half centuries as a Portuguese colony, its baroque churches and pastel-coloured townhouses a fading monument to the era when it had been, briefly, one of the wealthiest places on Earth. But the age of fabulously wealthy monopolies was permanently over. The 700,000 taels owed to the Suetsugu and Nakano families, the debt that had driven the embassy in the first place, was forfeited.

For Japan, the embassy’s destruction was a signal fire visible across East Asia. The message was not subtle, and it was not intended to be: the Tokugawa shogunate would kill diplomats. It would execute unarmed men who came bearing petitions. It would burn their ships and display their heads on pikes. The sakoku edicts were not posturing. They were policy, enforced with steel.

The Dutch, who had done so much to orchestrate the Portuguese expulsion, inherited the European monopoly on Japanese trade, but on terms so restrictive they would have humiliated a medieval vassal. Confined to Dejima, the same tiny artificial island where the Portuguese had been quarantined, the VOC factors endured annual inspections, restrictions on religious practice, and the ritual humiliation of the sankin kōtai journey to Edo, where they were expected to pay homage to the shogun. It was profitable enough to be worth the indignity, but only just, and the Dutch never forgot that their privileged position depended entirely on the continued goodwill of a government that had demonstrated, in the most graphic possible terms, what happened to foreigners who overstepped.

Chapter Eleven

The Calculus of Cruelty

The execution of the 1640 embassy is sometimes described as an act of barbarity, and by any humane standard it was. 61 unarmed men, including four elderly ambassadors who had come to talk, not to fight, were beheaded on a hillside for the crime of entering a harbour. But to read the event only as cruelty is to miss the point. The entire episode, the meticulous matching of executioners to prisoners, the gala-dressed ambassadors hearing their death sentence, the forced witnessing of the ship’s burning, the careful selection of survivors capable of delivering a coherent report, the cosmic defiance of the shogun’s final message, was a piece of political theatre designed to deliver a message.