In 1640, in a final attempt to keep trade and communication links open with Japan, a desperate Macau sent a delegation of traders and negotiators to that country. Their previous attempts had all been rebuffed since the general massacre of the converts in the Shimabara rising in 1637 - but with the loss of their other colonies, the Portuguese port of Macau was in dire straits.
The expedition ended disastrously, with many of its members being executed and the survivors left to bring back this following unequivocal message (via Macao: Mysterious Decay and Romance, edited by Donald Pittis and Susan J. Henders):
In our country, at the beginning of the Keicho period, when the Great Lord Minamoto occupied the ruler's seat, civil and military virtues distinguished themselves side by side. The generosity and the strictness of his rule were blended in perfect harmony. Then came the four kinds of Barbarians from the four quarters surrounding our country, asking for the opening of trade and intercourse. The office for supervising foreign shipping was accordingly established at the port of Nagasaki in Hizen. Merchants of all kinds frequented this port, buying and selling, going and coming continuously. The worm-like Barbarians of Macao who had long believed in the doctrine of the Lord of Heaven, wished to propagate their evil religion in our country; and for many years they sent people called 'Bateren' [Padre] on board their own ships, or in hired Chinese ships. They did this with the intention of seducing our ignorant people, thus paving the way for the eventual occupation of our country. On account of this, the Great Lord became angry, seized the Bateren and their converts, beheaded or crucified them in great numbers, and promulgated an edict strictly prohibiting that faith. Any converts found were to be punished with the utmost severity, not only themselves, but their parents, children, and relations as well.So the Japanese in one of their less-friendly acts of foreign relations. It does explain somewhat, though, how the psyche of Portuguese Macau may have been indelibly scarred by this incident; it certainly never attempted any similar such coups of diplomacy again in desperate circumstances, and seemed to maintain a cultural cynicism in dealing with neighboring powers that was never entirely eradicated.
From that time onwards, during the reigns of the three Shoguns, uncluded the late Lord [Hidetata] and the present Lord [Iemitsu], the faith of those miscreants became more hated, and the prohibitions increased in severity. Nevertheless, on the excuse of trading, Macao continued to send more Bateren, sometimes concealing them at the bottom of Chinese merchantships hired for that purpose. Thery also disguised themselves so that they could penetrate into the interior of the provinces of this country, seducing the ignorant people by their evil arts. The Barbarian ships, too, likewise afforded them concealment and protection. Therefore they were ferreted out and caught year after year, some being thrown down the great cliffs, and others being burnt to death [the author is clearly relishing this part - Ed.]
In addition to this, in the winter of the year of the younger brother of fire and the ox [1637- Ed.] , these evil people gathered together at Shimabara in Hizen. They attacked the villages, burned the houses, and killed the people. They repaired and dug themselves in at the old castl, where their stubborn resistance could not be overcome speedily. If we had not destroyed and annihilated them as quickly as possible, their numbers would have greatly increased, and the revolt would have spread like the rebellion of Chang Lu. In the spring of the year of the elder brother of earth and the tiger , the rebels were annihilated, about forty thousand being beheaded; but our own horse and foot soldiers likewise suffered bery heavy casualties in killed and wounded. The instigators of this revolt were deserving of the severest punishment, and therefore a government envoy was dispatched to Nagasaki, warning your people that they should never return to this country, and that if they did, everybody on board the ship(s) would be killed infallibly, etc. etc.
But now, in spite of this strict command, your people came again to this land under the pretence of peace negotiations, but the government officials have no proof that this is their real intention. We therefore had no alternative but to obey the existing order and could not spare their lives. We therefore destroyed the ship; arrested those on board; exposed the heads of the several chiefs except some sailors and the surgeon whose offence was not so grave in comparison with the several chiefs who were beheaded, and whom we ordered to report the facts to your country. They were therefore spared from execution, and it was arranged that they should be sent back in a small ship in order to bring this letter to Macao.
The elders of Macao and its dependencies when they hear of the foregoing facts must needs acknowledge the righteousness of our country and be impressed by the strength of our military virtue.