Along with Kazumasa ISHIKAWA, Naomasa made a significant contribution as a diplomat, of which there were few among the vassals of the Tokugawa clan, and, along with Masanobu HONDA, was regarded by Ieyasu as a man of wisdom needed to take the reins of government.
直政は石川数正と並んで徳川氏の家臣の中でも数少ない外交官として、大いに力を発揮し、また、家康から見て本多正信と並んで天下取りの知恵袋とされていた。