Punisher (Vol. 1) #3 Devil By The Horns
This is early on in Frank Castle’s war against the Gnucci crime family, they’ve already sent assassins after him as well as the man who recruited them putting Ma Gnucci on edge.
Punisher’s next target is Dino Gnucci, Ma Gnucci’s brother, Dino is standing trial. Dino is defended by Matt Murdock a.k.a. Daredevil. Punisher and Daredevil square off on a rooftop, Punisher gains the upper hand knocking Daredevil unconscious and tying him to a post. When Daredevil comes to he find himself chained to a post with a gun tapped to his hand, not knowing what’s going to happen next he sees Punisher with a rifle in his hands.
Frank reveals that he’s going to snipe and kill Dino Gnucci very soon unless Daredevil stops him, how you ask? Daredevil has to fire the gun tapped to his hand and kill Frank in order to stop him. In a twisted game designed to keep Daredevil out of his way as well as break him Frank takes aim and waits for Daredevil’s decision.
Punisher raises his rifle waiting for a clear shot or to be shot. Now Daredevil has a “No Kill” policy, only injuring and fighting the criminals, incapacitating them and killing someone would ruin his psyche. And that’s exactly what happened, Daredevil raised teh gun and pulled the trigger only to hear it go “click.” The Punisher reveals that he’s removed the firing pin in the gun, then Murdock breaks down realizing what he’s just done. Punisher kills Dino Gnucci and continues on his mission after releasing Daredevil to wallow in his uncertainty.