He was promoted to Captain in 1812, and the following year raised a company, for either the ongoing conflicts with indigenous people or the War of 1812 (accounts differ.)
He participated in the expedition of General Howard in 1813 and the Battle of Credit Island in 1814 in a military capacity.
[6] A 14-foot bronze memorial was erected in the courthouse yard in Fulton, Missouri, and dedicated in July 1905.
[7] In 1912, Willam Bocks Rigg (1874–1964) published a book of poetry that included stanzas leading to the death of Callaway.
210 of the American legion on July 13, 1941, erected and dedicated markers for the graves of three soldiers slain with Captain James Callaway by Indians on Loutre creek, Montgomery county, March 7, 1815.