The Keichō Embassy: A Samurai in the Court of the Spanish King

Chapter One

The Other Embassy

Thirty years after four teenage boys from Kyushu sailed to Rome and kissed the feet of Pope Gregory XIII, a very different Japanese embassy set out for Europe. Where the Tenshō Embassy of 1582 had been a Jesuit production, conceived by the Italian strategist Valignano, sponsored by Christian daimyō, designed to demonstrate the sophistication of Japanese civilisation, the Keichō Embassy of 1613 was something rawer, stranger, and more desperate: a gamble launched by a one-eyed warlord from Japan’s North, negotiated by a Franciscan friar with more ambition than judgement, and carried across three oceans on a ship built from Japanese cedar by Spanish shipwrights.

The Tenshō Embassy had been received with tears and trumpets. The Keichō Embassy would be received with polite suspicion, bureaucratic delay, and the quiet confiscation of its ship. The first embassy had arrived at the zenith of the Christian Century. The second arrived as the Century was collapsing, dispatched in the same year that the Tokugawa shogunate issued its definitive edict banning Christianity from Japan.

The timing was, to put it gently, unfortunate.

Chapter Two

The One-Eyed Dragon

Date Masamune was not a man who did things by halves.

The lord of the Sendai domain in northeastern Japan, a vast territory in the old province of Mutsu that the Spanish, with characteristic grandeur, referred to as the “Kingdom of Ōshū”, was one of the most formidable warlords of his generation. He had been blind in his right eye since childhood, an affliction that initially earned him a reputation for being slow and gloomy. The reputation did not survive his adolescence. By his late teens, Masamune was a battlefield commander of extraordinary ferocity who led from the front, killed enemy leaders personally, and was never beaten or captured. He maintained a standing army of 80,000 men and could raise a 100,000 in extremity.

His domain was enormous: over a thousand villages yielding more than 600,000 koku of rice. His castle at Sendai sat on a high bluff overlooking the Hirose River, chosen for its impregnability. His ambitions were larger than his domain. He had harboured plans to rule all of Japan, but his rise coincided with the consolidation of power under Hideyoshi and then the Tokugawa, and the window for independent conquest had closed. He submitted to Hideyoshi at Odawara in 1590, arriving dressed in white, the colour of death, to signal that he expected execution. Hideyoshi, amused or impressed, let him live.

Under the Tokugawa peace, Masamune’s samurai were idle and his ambitions were bottled. He needed an outlet. In 1611, a massive earthquake and tsunami devastated his coastline, and the economic imperative for new revenue streams became urgent. Somewhere in the intersection of restless ambition, fiscal necessity, and the availability of a Franciscan friar who spoke fluent Japanese and claimed to have the ear of the Spanish king, Masamune conceived a plan that was either visionary or delusional: he would send an embassy across the Pacific to negotiate a direct trade agreement with the Spanish Empire.

Chapter Three

The Friar

Luis Sotelo, a Spanish Franciscan of noble Sevillian birth, had been dispatched to Japan and had developed a deep knowledge of Japanese language and politics. He was intelligent, zealous, and possessed of an ambition that consistently exceeded his authority. He had been imprisoned in Edo for violating the shogunal ban on Christian proselytising, a ban that was hardening by the month, and it was Date Masamune who intervened to secure his release, recognising the friar’s usefulness as an intermediary with the Spanish colonial world.

The partnership between Masamune and Sotelo was pragmatic on both sides. Masamune wanted Spanish navigational expertise, Spanish silver-mining technology, and access to the trans-Pacific trade that the Manila galleons had been running between Acapulco and the Philippines for half a century. Sotelo wanted the Catholic mission in Japan to survive, or, more precisely, he wanted the Franciscan mission to survive, at the expense of the Jesuits, whose monopoly on Japanese evangelisation he resented with a bitterness that coloured every diplomatic communication he produced.

Sotelo framed the embassy in language calculated to appeal to Catholic Europe: Date Masamune was requesting Franciscan missionaries to convert his domain. The daimyō’s letters to the Pope and the King of Spain, drafted, in all likelihood, with heavy Franciscan coaching, described a pious lord eager to bring his people to Christ, held back only by “invincible motives” and “obstacles” from being baptised himself. The obstacles were never specified, because they were political rather than spiritual: Masamune was willing to tolerate Christianity, but he was not a believer. He was a strategist, and the embassy was a strategic manoeuvre dressed in vestments.

Chapter Four

The Great Ship

The San Juan Bautista was the physical embodiment of the embassy’s hybrid ambitions.

A triple-masted galleon of five hundred tons, built in the Spanish style from Japanese cedar and pine in Date’s coastal domain, it was four times larger than the previous trans-Pacific vessel constructed in Japan. It measured over thirty-five metres long, nearly eleven wide, and twenty-eight tall, a ship that announced its seriousness by its sheer mass. Its design combined Spanish maritime expertise with Japanese labour: the stranded Spanish general Sebastián Vizcaíno contributed his knowledge of galleon construction, the Tokugawa Admiral Mukai Shōgen sent workers north to assist, and some accounts suggest that Japanese carpenters trained by the Englishman William Adams may have helped as well.

The ship carried roughly a hundred and eighty people when it departed Tsukinoura on October 28, 1613: Hasekura Tsunenaga, Masamune’s retainer and the nominal ambassador; Sotelo, the Franciscan co-envoy and real diplomatic voice; Yokozawa Shōgen, a Date vassal serving as ship’s captain; ten Tokugawa retainers ensuring the shogunate’s oversight; forty Spanish sailors and pilots providing the navigational expertise that made the voyage possible; and a complement of Japanese merchants, samurai, carpenters, and tradesmen.

The San Juan Bautista would not return to Japan. Its fate was a microcosm of the embassy’s failure: confiscated by the Spanish, sold to a colonial governor at a bargain price, repurposed as a warship against the Dutch, and lost to history in the waters of the Philippines. The great galleon that Date Masamune had built to project Japanese power across the Pacific ended its career as a piece of Spanish military surplus.

Chapter Five

Three Oceans

From Tsukinoura, the San Juan Bautista sailed south to the Philippines, arriving in November 1613. From Luzon, it crossed the Pacific to Acapulco, arriving in January 1614, a passage of roughly three months across the largest body of water on earth, guided by Spanish pilots who understood the currents and the winds. In New Spain, the delegation made its way overland to Mexico City, where 78 Japanese members of the mission were baptised during Holy Week, a public spectacle that served as both spiritual milestone and diplomatic credential.

From Veracruz, the embassy sailed with the Spanish fleet across the Atlantic, stopping in Havana before making landfall at Sanlúcar de Barrameda on the Andalusian coast in October 1614. They had been travelling for a year. They were now in Europe, on the doorstep of the Spanish court.

Their triumphal entry into Seville on October 21, 1614, was a grand affair, the exotic Japanese delegation, with their swords and their silk, processing through the streets of the city that controlled the Atlantic trade, lodged at the Royal Alcázar. They moved on through Córdoba, Toledo, and Getafe, arriving in Madrid in December amid heavy snowfall. On January 30, 1615, Hasekura and Sotelo were granted a formal audience with King Philip III.

Hasekura’s baptism was staged in Madrid on February 17, 1615, deliberately delayed from Mexico to maximise its diplomatic impact. The Duke of Lerma, the king’s favourite, stood as godfather. Philip III himself attended. The ceremony was designed to demonstrate, in the most public and prestigious setting available, that Japan’s embassy was a Christian enterprise backed by a lord who was moving his people toward the faith.

Chapter Six

The Spanish Calculation

Philip III’s court received the Japanese with ceremony but denied them substance. The Council of the Indies, the bureaucratic body that governed Spain’s colonial empire, was deeply alarmed by the arrival of the five-hundred-ton Japanese galleon in Acapulco. Spain’s Pacific empire rested on its monopoly of the trans-Pacific sea lanes. A Japanese lord who could build galleons, hire Spanish pilots, and navigate independently between Asia and the Americas was not a trading partner. He was a strategic threat.

The alarm was compounded by intelligence arriving from Japan. The Tokugawa shogunate had issued its definitive anti-Christian edict in January 1614, the very month the embassy reached Acapulco. News of the edict, and of the mass expulsion of missionaries that followed, filtered to Madrid through Spanish colonial channels and through the reports of the embittered Vizcaíno, who had his own grievances against the Japanese. The embassy was asking Spain to invest in a commercial and missionary relationship with a country that was, at that very moment, demolishing its churches and deporting its priests.

Philip III ordered all mention of trade removed from his official reply. He expressly forbade Spanish sailors from helping the Japanese navigate future trans-Pacific voyages. The audience was generous in protocol and empty in outcome. The embassy had been heard and politely refused.

Chapter Seven

Rome: Pageantry Without Substance

From Spain, the embassy crossed to Italy, arriving in Genoa in October 1615 and processing to Rome. Hasekura made a solemn entry through the Porta Angelica on October 29, riding past Castel Sant’Angelo, crossing the Tiber, and proceeding to the Capitoline Hill, the same symbolic geography that the Tenshō ambassadors had traversed three decades earlier, though under vastly different circumstances.

Pope Paul V received Hasekura and Sotelo at the Quirinal Palace on November 3, 1615. The Roman Senate conferred the title of patrician and citizen on Hasekura, the same honour that had been granted to the Tenshō ambassadors. The Pope provided a gift of a thousand gold ducats and valuable religious objects.

On matters of policy, however, the Pope deferred entirely to Spain. Date Masamune’s requests, a new bishop for Japan, recognition as a sovereign Catholic king, the dispatch of Franciscan missionaries, were politely redirected to the Spanish crown, which had already said no. The papacy would not act independently of the Iberian Patronage system that governed Catholic missions in Asia. The embassy’s leverage, such as it was, had already been spent in Madrid.

Hasekura lingered in Rome. The city was hospitable. The substance was not forthcoming. By 1617, the embassy began its long journey home.

Chapter Eight

The Ship They Lost

Back in New Spain, the embassy found the San Juan Bautista quarantined by the Viceroy, who had no intention of allowing a Japanese-built galleon to return independently across the Pacific. The strategic logic was consistent with Spain’s refusal in Madrid: Japanese mastery of trans-Pacific navigation was to be prevented, not facilitated. The Viceroy ordered the ship to sail to the Philippines instead of Japan, and once in Manila, the Spanish Governor-General Alonso Fajardo purchased the vessel at a fraction of its value to use as a warship against the Dutch.

The Japanese envoys were stranded. Their ship was gone. Their mission had been refused. Their country was in the process of expelling the very missionaries they had offered to welcome. Hasekura remained in the Philippines until 1620, when he finally secured passage back to Japan on another vessel.

Chapter Nine

The Return to a Changed Country

Hasekura reached Sendai bearing a portrait of the Pope, a portrait of himself kneeling before a crucifix, and what the sources describe as “strange tales” of his travels. He bore no treaties. He bore no trade agreements. He bore no Spanish pilots or silver-mining experts.

The Japan he returned to was unrecognisable. The 1614 edict had been followed by escalating persecution. Churches were demolished. Missionaries were hunted. The Great Martyrdom of Nagasaki, fifty-five Christians burned and beheaded on Nishizaka hill, had occurred in 1622, two years after Hasekura’s return. The Tokugawa were dismantling the Christian Century with systematic violence.

Date Masamune, reading the political wind with the same ruthlessness that had kept him alive through four decades of Japanese power politics, abandoned his prior tolerance of Christianity immediately. Two days after Hasekura’s return, he issued an edict ordering all Christians in his domain to be exiled or executed. The daimyō who had written pious letters to the Pope about his desire to bring his people to Christ now presided over their persecution. The partnership with Sotelo, the Franciscan whose fluency and ambition had made the embassy possible, was repudiated entirely.

Hasekura died a year or two later. The sources do not record the cause. His family was subsequently disgraced, and his son was executed in 1640 for harbouring Christian sympathies, the final cost of an embassy that had sailed across three oceans to ask for something the world was no longer willing to give.

Epilogue

The Friar’s End

Luis Sotelo, blocked by Spanish authorities from returning to Japan, did what Jesuits and Franciscans had been doing for decades when told no: he went anyway.

In 1622, disguised as a merchant, he smuggled himself into Kyushu. He was quickly captured. He was burned alive at the stake in 1624, one of the last foreign missionaries to die in the persecution, a Franciscan martyr in a country that had no further use for Franciscan diplomacy.