Charlie Le Flore (also Laflore) was captain of Indian police, deputy US marshal and special agent for the Missour, Kansas and Texas Railroad—all at the same time. The Choctaw Indian had a close encounter with the Daltons in July 1892.
He and seven lawmen were on board a train that stopped at Adair, OK, where the Daltons awaited. A gunfight broke out. Le Flore and two other officers were slightly wounded in the battle. The outlaws got away, but only with a small amount of money.