History is littered with grand projects and dashed expectations that are no less intriguing than its moments of triumph and heroism. A large portrait in oils of a splendidly attired, mid-ranking samurai posing regally in a Roman palace in the early 1600s bears witness to one such episode.

In 1613, the same year that the British East India Company’s ship, the Clove, arrived in south-western Japan, a galleon carrying an embassy of Japanese left from the northeast in the opposite direction. This was not the first delegation sent from Japan to Europe; in 1582, four teenage boys were sent by three Christian daimyo of Kyushu to pay their respects to the Spanish king and the pope.

However, orchestrated by daimyo Date Masamune (1567-1636) and backed by retired shogun Tokugawa Ieyasu (1592-1616), the 1613 voyage is considered to be Japan’s first official embassy to Europe. The delegation’s mission was to obtain permission from King Philip III of Spain and Pope Paul V to trade with Nueva España (colonial Mexico), and request more Christian missionaries. Masamune, who eliminated his younger brother, conquered his relatives’ lands and is rumored to have gouged out his own eye, possibly also saw an opportunity to acquire Western military technology.

The delegation was headed by Masamune’s retainer Hasekura Tsunenaga (1571-1622) and the Spanish friar Luis Sotelo (1574-1624). The son of an official who had been ordered to commit suicide over allegations of corruption, Tsunenaga was fortunately deemed to be more useful to his domain alive and was spared a similar fate.

Embarking from Sendai, the purpose-built galleon Date Maru followed the trade winds of the 38th parallel north across the Pacific Ocean to Cape Mendocino, the western-most point of Nueva España, present-day California. From there, the ship followed the coast south to the port of Acapulco. The embassy crossed overland to Veracruz before traversing the Atlantic Ocean via Cuba, arriving in Spain in October 1614.

During his eight months in Spain, Tsunenaga was baptized and met with King Philip III and the Spanish Council of the East Indies. However, concerned about the increasingly hostility of the shogunate toward Christianity, the Spanish authorities refused the requests for trade agreements and missionaries. An oil-on-linen portrait of Tsunenaga in prayer, designated a National Treasure, survives from this sojourn, but interested parties will need to travel to Sendai City Museum in Miyagi Prefecture to see it.

Tsunenaga continued on to Rome to bring his petition before the pope. Although an obscure civil servant from what was then regarded as a remote and idolatrous land, he was heralded with trumpets and escorted on horseback to an audience with the pope and his cardinals in November 1615. This exaggerated display of warmth suggests that this visitor from afar affirmed the position of global spiritual and political leader to which the Borghese pope aspired.

Tsunenaga presented His Holiness with two letters from Masamune, promising to foster the propagation of Christianity in his domain. These documents, one in Latin and the other in Japanese, remain in the Vatican archives. Tsunenaga was granted a certificate of Roman citizenship, which is preserved at Sendai City Museum.

The pope’s nephew Scipione Borghese (1577-1633) commissioned an enormous portrait from painter Archita Ricci (1560-1635). The artwork, which forms the centerpiece of a small display at the Tokyo National Museum, depicts Tsunenaga resplendent in white robes and hakama trousers with a pair of swords at his waist. His raised brows and upper lip lifted slightly to reveal his front teeth — an unusual feature in formal portraiture — suggest expectation. His slightly incongruous embroidered stockings and shirt may have been the painter’s invention, but after several months in Europe it is not impossible that Tsunenaga began to alter his attire. Tsunenaga wears a similar robe in the fresco of Sala Regia in Vatican City, where he is shown with Luis Sotelo among other foreign emissaries.

An inventory of symbols elaborates on the identity of the subject. In the upper left, Tsunenaga’s family crest is paired with a crown, suggesting that he was considered an honorary member to the Roman aristocracy. At his feet, a spaniel signifies loyalty. Through a window on the far right, the Holy Spirit depicted as a dove hovers over Saint Francis and allegorical figures. Below this, the Date Maru, renamed San Juan Bautista, bears the crests of the Date and Hasekura families.

Despite this exhibit of friendliness, the pope was reluctant to overrule the Spanish court’s decisions, which had rejected a second application for permission to trade from Tsunenaga. Tsunenaga retraced his route back to Japan via Manila, depositing crew members on the way, who intermarried with the local peoples. He died in 1622, a year after his return. His son, wife and servants were killed during anti-Christian purges in the 1630s-40s. The shogunate limited diplomatic ties with Europe to those with the Dutch, and relationships with Italy and Spain were not established until 1866 and 1868 respectively.

The Archita Ricci portrait is displayed alongside two sets of screens, “Map of the World’ and “Europeans in Japan,” both created around the time of Tsunenaga’s voyage. Aside from giving context, they speak of the ardent fascination the world held for the people of Japan and how they imagined themselves within it.

“Portrait of Hasekura Tsunenaga and Nanban Art: Japan-European Exchange 400 Years Ago” at the Tokyo National Museum runs till March 23; open 9:30 a.m.-5 p.m. ¥600. Closed Mon. www.tnm.jp/modules/r_free_page/index.php?id=1649