At What Point Does Asuma Sarutobi Find Out About Kurenai?
As he asks Shikamaru who the &quot;King&quot; is we can conclude that he already knew that Kurenai was pregnant. He wanted Shikamaru to know that so if anything happened to Asuma, Shikamaru would protect the &quot;King&quot; aka Mirai Sarutobi. The &quot;King&quot; as Shikamaru came to realize were the people that he held dear.