Task and Purpose has a good article up where they try to decipher what makes Punisher iconography so attractive to those being sent down range. Its popped up increasingly in the past couple of decades and isn’t going away any time soon.
“I find it flattering, but also a little unnerving because I never actually felt the Punisher was one of the good guys,” said Gerry Conway, one of the character’s original creators, of the character’s popularity in the military. “I don’t think the Punisher is a hero; he’s an anti-hero. He’s someone that rises up from our subconscious and acts on our behalf and is a symbol really of cultural breakdown.”
Conway explained that the Punisher is “a dark vision of the effect of social breakdown.”
If the Punisher shows up, then something has gone horribly wrong. But in a world of complex and nebulous threats where nothing is simple, the character offers readers a direct solution to incredibly complicated problems.