Simple logic would dictate that the Kingpin would be the Punisher’s number one target in Marvel Comics, but his reason for not killing Wilson Fisk is genius. The Punisher first crossed paths with Kingpin in 1989’s “Kingpin Rules” storyline running through issues 14-18 of his solo title. The story was written by Mike Baron and illustrated by Whilce Portacio.

The Punisher was born in tragedy; ex-Marine Frank Castle’s family was gunned down in front of him. The loss shattered Castle, turning him into the murderous Punisher. He embarked on a one-man war on crime, and the deeper he went into it, the more inevitable a showdown with the Kingpin became. As one of the figureheads of organized crime in the Marvel Universe, the Kingpin has been untouchable by heroes ranging from Spider-Man to Daredevil. These heroes play within the bounds of the legal justice system, which Kingpin has weaponized, allowing him to continually get away with his illicit activities. However, the Punisher has little use for the rule of law, freely executing any criminal who crosses him. Interestingly, it would be nearly 15 years into the Punisher’s existence before he first encountered Kingpin.

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In issue 14, the Punisher poses as a substitute teacher to infiltrate a New York City school that has been taken over by a low-level criminal named Winston, who has ties to the Kingpin. After busting up the racket in the school, the Punisher was finally on the Kingpin’s radar, and in issue 15, readers learn that both the Punisher and Kingpin knew it was only a matter of time before they encountered each other. Knowing that the Kingpin will be a foe unlike any other, the Punisher and his quartermaster Microchip enlist the help of the Punisher’s friend Ortiz, another teacher at the school named Mister Brooks, and a student named Reese McDowell. The Kingpin unleashed Hell on the Punisher and his allies, and in issue 16, one of Kingpin’s hired goons kills Reese. After Ortiz is killed in issue 17, the Punisher and Brooks vow revenge.

The Punisher decides not to kill KIngpin

The story culminated in issue 18, with a rooftop showdown between the Punisher, Brooks, Microchip and Kingpin. After all the suffering the Kingpin reigned down upon the Punisher and his allies, he is ready to pull the trigger and rid the world of Wilson Fisk once and for all. However, Brooks and Microchip refuse to kill Kingpin. Their reasoning is that when Kingpin dies, it will create a power vacuum and the scramble to fill it will be bloody, resulting in many civilian deaths. The Punisher begrudgingly spares the Kingpin’s life after seeing their point.

Kingpin is one of the vilest villains in the Marvel Universe, who, thanks to his imposing figure and ruthless instincts, has created a criminal empire unlike any other. He hides behind the law, taking advantage of technicalities; he also bribes and blackmails people. In short, he is everything the Punisher detests. The Punisher had the Kingpin right where he wanted him and had the opportunity to rid the world of him once and for all. However, the Punisher had to accept Microchip and Brooks’ logic that the Kingpin’s death would only lead to more death and destruction. Once again, Kingpin got off the hook, and proved himself untouchable, even by the Punisher. The Punisher came close to killing Kingpin, but chose not to, realizing that Wilson Fisk’s death could lead to a worse situation.

Next: The Punisher Knows Who His Last Kill Will Be (And Why They Deserve It)