When Norman Osborn rose to power, he sent Wolverine's son after the Punisher, and Frank Castle didn't walk away from their fight.
In the world of Marvel comics, Frank Castle, aka the Punisher, is arguably the most dangerous non-powered human there is. Driven by an endless well of vengeance, the Punisher has killed his way back and forth across the criminal underworlds of countless countries, always eventually returning to New York, and the latest cadre of mobsters for him to cull.
But even the most dangerous human can't compete forever in a world of wonder, and during Marvel's Dark Reign even, the tide suddenly turned against Frank, and the son of his old ally Wolverine - the mutant known as Daken - took him down in a hyper-violent fight to the death that literally left the Punisher in pieces.
The slaughter happened in Dark Reign: The List - Punisher, part of a series in which Norman Osborn - having taken over Nick Fury's position following the Skrull invasion of Earth - resolved to wipe out heroes he considered particular threats to his power or the world at large. Osborn's case against the Punisher was actually watertight, born of a fear that Frank would kill the wrong person and bring about World War III - exactly what happened in the alternate universe of Marvel Universe vs. The Punisher. Understanding that Nick Fury always gave Castle a little latitude, Osborn resolves to do what he couldn't, committing all the resources of his new organization to wiping out the vigilante.
The Punisher is on top form, escaping an unannounced missile barrage by using stolen Pym Particles to shrink down and escape. But as an organization the size of SHIELD steps up its pursuit, the Punisher uses up his varied collection of weaponry and begins taking injuries. Dissatisfied with his soldiers' progress, Osborn unleashes Daken. Wolverine's estranged son, full of hatred towards his father, had previously agreed to become a fake "Wolverine" in Osborn's Dark Avengers. With Wolverine's claws, healing factor, enhanced senses, and his own unique mutation of pheromone control, Daken takes a huge amount of abuse from the resourceful Frank but ultimately corners him on a rooftop.
Incredibly fast, unkillable, and able to throw off the Punisher's senses, Daken gains the upper hand, slicing off Frank's arm and preparing for the killshot, saying, "Hell, look at your monkey-face-- don't even look surprised. If I didn't know better, I'd say you look relieved." With that, he beheads Frank, slicing his body into many pieces which scatter in the alleyway below. As he dies, the Punisher says he can see his wife Maria waiting for him, though the title that adorns the final page, "A Good Lie," clarifies that he knows he isn't bound for Heaven.
Dark Reign saw the bad guys take over the Marvel Universe, and Daken's execution of the Punisher was a huge statement that the change wasn't merely cosmetic. Worse, this wasn't the usual case of one character being mind-controlled or recently depowered: Punisher and Daken's combat was a fair fight, and while Daken only triumphed because of his powers, he definitively proved himself the deadlier fighter. Rick Remender's terse writing and John Romita Jr.'s brutal art help to make this not just a temporary setback, but the Punisher's ultimate defeat at the hands of someone quicker, meaner, and younger.
Frank was resurrected later - sewn back together into the zombie Franken-Castle and healed through the cursed magic of Marvel's Bloodstone - but even this unusual reversal was a testament to the fact that the death changed how Frank was seen. The Punisher's greatest asset has always been his reputation as a Batman-style warrior who can out-plan any opponent, but his defeat at the hands of Wolverine's son proved once and for all that the character has limits. In a world of marvels, even the Punisher can die.
