The Punisher famously doesn’t hurt law enforcement, but he broke that rule to take out one of Spider-Man’s closest allies and hurt the Kingpin.
Despite famously having rules against harming legitimate law enforcement, the Punisher once broke his rule about killing cops to take out an iconic Spider-Man ally. In the Ultimate universe, Frank Castle is a former cop who seeks vengeance against all criminals when his family are killed. Seeing no difference between costumed criminals and crooked cops, the Punisher interrupted a fight between Moon Knight, Spider-Man and Daredevil to kill NYPD Captain Jean DeWolff, Spider-Man’s police confidant who – unbeknownst to him – was in bed with the Kingpin in more ways than one.
In the mainstream Marvel universe, Captain Jean DeWolff was an NYPD lieutenant who maintained a strong relationship with Spider-Man despite the animosity shown to him as a vigilante by other uniformed police officers. Tragically, Jean was killed by Detective Stan Carter, a fellow cop and former lover, as part of his lethal campaign as the Sin-Eater. In the Ultimate universe – a parallel Marvel dimension that offered modern, reimagined stories unburdened by decades of continuity – Captain DeWolff helps the young Spider-Man by offering him advice and consultation, but her true loyalty is to Spider-Man’s longtime enemy the Kingpin.
In the Ultimate Spider-Man Annual #2 by Brian Michael Bendis and Mark Brooks, Captain DeWolff assists the Kingpin’s endeavors by pointing Spider-Man in the direction of Frank Oliver, aka the Kangaroo, a new crime lord aggressively trying to move in on Fisk’s territory. When Daredevil’s fight with the Kangaroo is interrupted by Spider-Man and the Punisher, Peter simply webs up the vengeful vigilante. While the costumed superheroes are distracted, the Punisher is able to free one of his hands and shoot Captain DeWolff, who dies in Spider-Man’s arms.
The corruption of Jean DeWolff is one of the many examples of the Ultimate universe reinventing classic Marvel characters in a completely new light. While maintaining the familiar relationship with Spider-Man, she becomes another way for the Kingpin to exploit and manipulate the young hero. Although one could argue this is another example of Peter’s recklessness and poor judgement, Jean DeWolff’s betrayal is even more devastating because Spider-Man had no idea. When he is angrily pummeling the Punisher for what he did, he is stopped by Daredevil, who confirms that Jean was not only working for Fisk but was also romantically involved with him.
The mainstream Punisher has made it clear that he does not fight the police, allowing himself to be taken in when hurting law enforcement is the only way to escape. It was therefore particularly shocking when this was not the case for the Ultimate Punisher, who happily ends the career of a corrupt officer in order to strike a blow against the Kingpin. While the mainstream Jean DeWolff’s death weighed heavily on Spider-Man, her death in the Ultimate universe was even more traumatic, as Peter misjudged the situation in several ways, from trusting Jean to believing the Punisher was out of action.