Monticello Drill Posted by Matt Little on 29th Oct 2025 "When you decide to attack, keep calm and dash in quickly, forestalling the enemy...attack with a feeling of constantly crushing the enemy, from first to last." - Miyamoto Musashi The Monticello Drill is a drill I created as a young police officer. My theory behind this was that it was more difficult for an untrained shooter to track across their body when they drew than away from their body. Especially because most of the untrained shooters we encountered in Chicago shot strong hand only rather than with two hands. The other theory behind the drill was that at five to fifteen yards, in the absence of cover, it was better to press the opponent while advancing rather than retreating while firing. The course of fire was to draw while taking a large aggressive step to the right or left, and then advance to approximately three yards from the target while shooting on the move. This creates psychological pressure on the opponent, seizing the initiative and overwhelming him through violence of action. I practiced this drill extensively for several years, and then shortly after returning from a tour in Iraq I was placed in the exact situation I had theorized when creating the drill. I was in a gunfight in an alley of Monticello Avenue on the West Side of Chicago where the offender drew and fired at me from approximately seven yards. Since there was no cover, I responded exactly as in the drill I had created. The tactic worked as I had theorized, and I was able to win that engagement without being injured. As an applications drill, the Monticello Drill combines lateral movement, drawing, and shooting on the move. It also represents a proven self-defense engagement sequence. I use this drill extensively in my Pistol Skill Applications class and believe strongly in its value.