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In 1621, now serving as head of the ''Nihonmachi'' and acting as representative of the royal court, Nagamasa sent three letters to Shogun [[Tokugawa Hidetada]] and two of the ''[[roju|rôjû]]'', in advance of Ayutthaya sending an embassy to [[Edo]] to negotiate for formal relations. This marks the first time anyone in the shogunate heard of (or from) Nagamasa, and as a result of [[Ishin Suden|Ishin Sûden]] investigating the identity of this mysterious "Yamada Nagamasa" and then recording it in his ''[[Ikoku nikki]]'', it also marks Yamada's first appearance in official shogunate documents.
In 1621, now serving as head of the ''Nihonmachi'' and acting as representative of the royal court, Nagamasa sent three letters to Shogun [[Tokugawa Hidetada]] and two of the ''[[roju|rôjû]]'', in advance of Ayutthaya sending an embassy to [[Edo]] to negotiate for formal relations. This marks the first time anyone in the shogunate heard of (or from) Nagamasa, and as a result of [[Ishin Suden|Ishin Sûden]] investigating the identity of this mysterious "Yamada Nagamasa" and then recording it in his ''[[Ikoku nikki]]'', it also marks Yamada's first appearance in official shogunate documents.
By [[1624]], Nagamasa was wealthy enough to purchase his own ship, which he sent to Nagasaki in the hopes of obtaining a ''shuinjô'' (red seal license). He was not granted one until a full year later, however, and so his ship remained in Nagasaki harbor, finally returning to Ayutthaya in [[1626]]. Nagamasa was able to secure some space on a Dutch ship to send a load of deerskins to Nagasaki on commission (i.e. in his own name, for his own profit), and also to send his own ship the following year, in [[1627]]. On this latter journey, the ship was captured by the Dutch, but once [[Jan Pieterzoon Coen]], governor of the Dutch East Indies, realized whose ship it was, he granted Nagamasa a license to trade in [[Batavia]] (Jakarta) and sent the ship freely back to Ayutthaya; Nagamasa sent a load of gifts to Batavia in response, and for the next year or two enjoyed a friendly and profitable personal trading relationship with the VOC. His ship traveled to Japan for the third and last time in [[1629]], after which it returned to Ayutthaya once more.<ref>Polenghi, 49.</ref>
When King Songtham fell ill in [[1628]], he named a relative, known as the Kalahom (a military title), along with Yamada, to serve as regents for his underage successor. The Kalahom then began engineering the deaths of his political rivals, eventually ending in the death of the young king in [[1629]]; when a rebellion arose in the southern province of Ligor, the Kalahom suggested that if Yamada led forces to suppress the rebellion, he could then become lord of that province. Yamada succeeded in this endeavor, and established himself and his Japanese compatriots as rulers of Ligor. In the meantime, however, the Kalahom seized the the throne, naming himself King Prasat Thom.
When King Songtham fell ill in [[1628]], he named a relative, known as the Kalahom (a military title), along with Yamada, to serve as regents for his underage successor. The Kalahom then began engineering the deaths of his political rivals, eventually ending in the death of the young king in [[1629]]; when a rebellion arose in the southern province of Ligor, the Kalahom suggested that if Yamada led forces to suppress the rebellion, he could then become lord of that province. Yamada succeeded in this endeavor, and established himself and his Japanese compatriots as rulers of Ligor. In the meantime, however, the Kalahom seized the the throne, naming himself King Prasat Thom.
