Batman #169: "Partners in Plunder"

Here's a little side trip to the Silver Age, an issue of Batman that has him matching wits with himself.
This is an interesting little story from an era notoriously light in substance. The line of Batman books had been recently invigorated with a new editorial direction (called "The New Look.") For the first time in many years, Batman and Robin were allowed to fight crime instead of aliens and robots.
What's interesting is that, during these years, the Dynamic Duo fought plain-clothed gangsters more often than the deformed/costumed criminals they are best known for. During the first year the Joker, Penguin and the Riddler all made an appearance in either Batman or Detective, but the creative team seemed more interested in inventing new villains.
Batman #169 is the first appearance of the Penguin in the "New Look" era, but he's changed little from his early days. He's still obsessed with umbrellas and how they can be used in crime, and has no overt interest in hurting anyone.
His plan in this issued, titled "Partners in Plunder," is surprisingly clever, though. He begins a wave of chaos in Gotham, flooding streets and stores with wacky umbrellas that cause a lot of confusion — but there doesn't appear to be method to the madness. Batman is sure the Penguin is responsible, but can neither prove it nor figure out the point to it all.
The reason is simple: the is no point. The Penguin's plan is to create a criminal "Rorshach blot" layered in possible clues and symbols that have no meaning. He's convinced — rightfully so — that Batman will infer what he will from the "clues" and find a way to keep the Penguin from reaching the alleged goal. Little does he know that the Penguin planted listening devices in a few of the umbrellas confiscated by Batman. He's been listening in on the Dynamic Duo's speculations and likes what he hears. He also know how Batman plans to stop him, which gives him the edge.
Even though he successfully pulls off the scam Batman has unwittingly planned for him (the theft of a jeweled meteorite) he fails to get away. During a chase using rocket umbrellas, Robin's lighter weight allows him to overtake the Penguin and throw a lasso around him. It's a victory for the Dynamic Duo, but not one they necessarily earned.