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Yamada then made his way to Siam. It is unclear when this took place, or aboard what type of ship. Historian Cesare Polenghi writes that Nagamasa found a job as a dockworker in [[Sakai]], joined the crew of a [[shuinsen|red seal ship]] bound for Siam in [[1612]], and arrived in Ayutthaya some ten weeks later, after stopping at a number of other ports.<ref>Polenghi, 2.</ref> However, Polenghi also writes that "the year of Nagamasa's departure [from Japan] is not known,"<ref name=pol17>Polenghi, 17.</ref> and that it can only be estimated based on [[Dutch East India Company]] factor [[Jeremias van Vliet]] having indicated that Nagamasa's Siamese-born son Oin (aka Ockon Senaphimuk) was ''about'' eighteen years old in 1630. Polenghi then suggests a number of different possibilities for Nagamasa's arrival in Ayutthaya, including having traveled there on a Japanese ship, on a European ship, or via elsewhere in Southeast Asia.<ref name=pol17/>

Yamada then made his way to Siam. It is unclear when this took place, or aboard what type of ship. Historian Cesare Polenghi writes that Nagamasa found a job as a dockworker in [[Sakai]], joined the crew of a [[shuinsen|red seal ship]] bound for Siam in [[1612]], and arrived in Ayutthaya some ten weeks later, after stopping at a number of other ports.<ref>Polenghi, 2.</ref> However, Polenghi also writes that "the year of Nagamasa's departure [from Japan] is not known,"<ref name=pol17>Polenghi, 17.</ref> and that it can only be estimated based on [[Dutch East India Company]] factor [[Jeremias van Vliet]] having indicated that Nagamasa's Siamese-born son Oin (aka Ockon Senaphimuk) was ''about'' eighteen years old in 1630. Polenghi then suggests a number of different possibilities for Nagamasa's arrival in Ayutthaya, including having traveled there on a Japanese ship, on a European ship, or via elsewhere in Southeast Asia.<ref name=pol17/>

Once in Ayutthaya, [[Kiya Kyuemon|Kiya Kyûemon]], head of the Japantown, took Yamada under his wing. Yamada also began studying Siamese and at least one European language, and soon found a job working as a middleman in the lucrative deerskin trade. At some point while in Siam, or perhaps during his time in Sakai, Yamada Nizaemon took on the name Nagamasa.

Once in Ayutthaya, [[Kiya Kyuzaemon|Kiya Kyûzaemon]], head of the Japantown, took Yamada under his wing. Yamada also began studying Siamese and at least one European language, and soon found a job working as a middleman in the lucrative deerskin trade. At some point while in Siam, or perhaps during his time in Sakai, Yamada Nizaemon took on the name Nagamasa.

At one point, Yamada traveled to the northern borders of Siam, and volunteered to help fight alongside Siamese warriors against a Burmese invasion. Killing the Burmese general, he found himself invited to the royal palace by King [[Songtham]], and granted aristocratic title. When Kyûemon decided to return to Japan, he named Yamada his successor; by this time, Yamada had become a head of the royal guards, and a wealthy merchant in his own right, even owning his own ship.

At one point, Yamada traveled to the northern borders of Siam, and volunteered to help fight alongside Siamese warriors against a Burmese invasion. Killing the Burmese general, he found himself invited to the royal palace by King [[Songtham]], and granted aristocratic title. When Kyûzaemon decided to return to Japan, he named Yamada his successor; by this time, Yamada had become a head of the royal guards, and a wealthy merchant in his own right, even owning his own ship.

In [[1621]], 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]], 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.