On the street they actually fight well together. Frank brings a soldier's planning, an arsenal, and nerves of steel; Spider-Man brings speed, webs, and a knack for keeping bystanders safe. When they pool those skills against organized crime, few gangs stand a chance.
But the partnership always runs into the same wall. Spider-Man will not take a life, and the Punisher will. That single rule keeps them from ever being true friends. They respect each other, they save each other, and then they part ways, each convinced the other is making a mistake.
The two met in The Amazing Spider-Man #129 (1974). The Jackal, hiding his identity, convinced the newly arrived Punisher that Spider-Man was a cold-blooded murderer and hired Frank to gun him down. The Punisher stalked the wall-crawler across the city, but the more he watched Spider-Man in action the more the story fell apart. Realizing he had been manipulated, Frank turned his weapons on the Jackal instead. That first encounter set the template for everything after: a soldier who kills and a hero who never will, sizing each other up and never quite agreeing.
Frank Castle has remained a grim solo operator, and in recent years Marvel has moved the character away from his classic skull emblem following the 2022 Jason Aaron series in which he led the ninja cult the Hand. His bond with Spider-Man stays exactly where it has always been: a recurring, uneasy alliance. Frank respects Peter's skill and his heart but rejects his refusal to kill, while Spider-Man keeps trying to pull Frank back from the edge. They help each other when the stakes are high, then go their separate ways.
Frank Castle was a decorated Marine who came home to New York and lost his wife and two children when they witnessed a mob killing in Central Park. When the courts let the gunmen walk, Frank declared his own war on crime and became the Punisher, hunting criminals with military precision and a skull painted across his chest.
He has no superpowers at all. His edge is training, discipline, and an enormous arsenal: he is a master marksman, a hardened hand-to-hand fighter, an expert in tactics and demolitions, and utterly relentless. Among the costumed cast around Spider-Man, that ordinary-but-lethal quality makes him stand apart.