Jim Masterson isn’t as well known as his brother Bat, but he actually spent more time in law enforcement than his older sibling; about 17 years.
His best known encounter was against the Doolin Gang at the Battle of Ingalls in 1893. A group of U.S. marshals tried to surprise the outfit one early morning. They were spotted, a gunfight ensued and three officers died.
Masterson brought things to a halt when he threatened to blow up the outlaw headquarters with dynamite, forcing the one remaining bandit to surrender.