The first train robbery was in Randolph County Missouri at the city of Allen in August 1861. Capt. Poindexter a Confederate Officer, took the money from a train of the N.E. Missouri R.R. The money had been taken by Union authorities from the bank in Fayette Missouri. The money was returned to the bank by Capt. Poindexter.
Poindexter possessed other skills, a persuasiveness of word and manner whose value his superiors recognized. Soon after Wilson's Creek, the Captain was detached on recruiting duty, returning to his home country in and around Randolph County. There his first action of note was on the sultry afternoon of August 28, 1861. Leading a small detachment of Confederate troops, he held up the North Missouri Railroad at Allen. They reportedly came away with three trunks of money, totaling $100,000 in coin, which belonged to the Missouri State Bank in Fayette. A subsequent newspaper article revealed that the money shipment was engineered by a Unionist "committee," in an attempt to spirit the coin out of Missouri, and away from the potential hands of Secessionists. An odd twist to an odd story is that Poindexter's Rebel rabble is subsequently reported as having returned the money to the Fayette bank. Peculiarities aside, this may be the first train robbery in American history.