(Target Comics v1 002, 1940)
Big Shot, a New York gang boss with a European spy named Drusella as his companion (a slight speculation as some imprecise speech balloon tails make it hard to be entirely sure just who is talking about what, but the details seem to fit), is after the technological advances that the Skipper has made in Boystate, with an eye toward using them to take over the world. His initial plan - drive up to the front gates and wing it from there - doesn't bear fruit, so he is forced to improvise a real plan on the spot. Also please note that the Skipper is on to Big Shot from the very start thanks to mind-reading technology that one of the Boystate Rangers tells Big Shot about. This whole three-part story functions mostly as a demonstration of Boystate's power for the reader.
Since the Skipper's stated mission is to take lost and abandoned boys and turn them into upstanding American men, Big Shot's new plan involves recruiting a suitably wayward youth to infiltrate Boystate and do a little espionage. His chosen agent is the unnervingly-named Pretty Boy, a would-be gangster with a world-weary attitude.
Pretty Boy is delivered from the harsh streets of NYC, where a boy might get beaten up by a grown man and forced into a life of crime, to the nice streets of Boyville, where boys are beaten up by their fellow boys in order to impart solid moral lessons. The nuance is unfortunately lost on him, and Pretty Boy sets out to fulfill his mission in the most direct manner possible.
There's some shenanigans involving a brief accidental foray into space as Pretty Boy steals an aircraft that he has no idea how to fly, but the end result is his delivering to Big Shot a bug-o-plane, a cosmic ray gun and the Skipper's chief aide the Captain, at which point Big Shot tosses both the Captain and Pretty Boy into the skeleton-filled dungeon pit that he has had installed in his NYC penthouse apartment.
At this point, Pretty Boy begins to see the error of his ways, and after some weeks of imprisonment and privation manages to make his escape and head back to Boystate for help.
Once the Skipper and his personal child army are on the case, it's all over for Big Shot. He doesn't even get the satisfaction of executing his prisoner thanks to the repentant Pretty Boy.
And speaking of Pretty Boy, he reforms and sheds his former, weird-to-type-this-many-times-in-short-succession name for the impersonal M-4 as he joins the Boystate Rangers and trades in his former rough and tumble lifestyle for one of blissful militarized conformity.
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