In the far future, a group calling themselves the Punishers run into a shantytown, burn it down, kill all the men, and steal all the children. Old Man Logan follow and finds the aftermath. A woman tells him what happened and follows the trail of the Punishers until they return to their stronghold. He's shot on the approach, and he receives help from an unlikely source: Frank Castle himself.
In a follow-up story, we follow the Punisher immediately after the Fall.
Old Man Logan Annual #1 returns to the native time-period of the elderly Wolverine. It blends Mad Max and Unforgiven and succeeds in its ability to be self-aware without being sanctimonious.
It's a narrative about violence breeding violence. Frank Castle is a man who kills violent criminals, and the Punishers took his philosophy and turns it into a cult that kills the old and raises the young in the hopes of being better. This perversion of his already reprehensible practices forces Frank to reflect on what he's become.
Logan serves a good guide for Frank on this personal journey, as he's already on the other side of similar realizations about himself.
The climax is still an ultraviolent siege against the Punishers carried out by Logan and Frank. Arguably, this undercuts the almost metanarrative remorse from Frank Castle that people took up his cause. The comic arguably justifies it by having the Punishers be truly cruel individuals. Your mileage may vary on either of these points; I struggle to support either with confidence.
The follow-up story elaborates on Frank's wavering faith in his chosen profession by having him refuse to arm prisoners he set free. He doesn't want the violence to spread.
Simone de Meo portrays the pain, violence, and expression in the first story with aplomb. The pliability and at-times almost cartoonish faces are a bit of a problem for the tone at times, but this doesn't sink the more dramatic moments. Dono Sanchez-Almara supports it with a well-balanced color palette. Hayden Sherman brings his distinctly gritty and lining-heavy style to the second story, and it serves it well. Sanchez-Almara colors this section well too.
Old Man Logan Annual #1 is an excellent journey through an individual's pain and regret due to the violent life they've led. Logan and Frank make for a great team in this pained mission to stop the ideological descendants of the Punisher. This one comes with a strong recommendation. Give it a read.