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The Enterprise is about to arrive at a world, Sigma Iotia II, which was visited over 100 years earlier by the Horizon. The Horizon was lost with all hands, and the planetary system is so far from the main Federation systems that the ship's report on the visit just arrived. The interesting aspect is that the Horizon visited the planet before the Prime Directive was enacted, and so they were free to meddle with the culture at will. The planet had just begun industrializing at the time of the visit. Kirk, Spock, and McCoy discuss their interest at seeing what resulted.
The leader of the planet they contact is "Boss" Bela Oxmyx. Kirk, Spock, and McCoy beam down and discover what looks just like a street scene from the Earth in the 1920s, with period cars and clothing. An important difference, though, is that everyone is armed: the men with tommy guns, and the women with handguns. Oxmyx's men arrive and promptly pull guns on the Starfleet men, using some colorful slang from the 1920s. As they are escorted to Oxmyx, some men in a car stage a drive-by shooting, killing one of Oxmyx's men.
When they arrive at Oxmyx's headquarters, they find him surrounded with plush accommodations and a pretty woman waiting on his every need. It seems that the entire planet is run by mob families, and Oxmyx's family is the largest one. The Starfleet men discover "the book": a book on the history of Chicago mobs that was left behind by the Horizon. Apparently the natives gradually modeled their whole culture after the mob culture described in the book.
Oxmyx knows that the Starfleet men are from the same "outfit" as the Horizon, and he's also clever enough to realize that in 100 years, the Federation's technology has probably advanced quite a bit. He wants some advanced weapons and training so he can knock off the other families and take over. When Kirk refuses, Oxmyx sends them off under guard to rethink their decision. Then he contacts Oxmyx through their communicators and manages to tell Scotty that he's got hostages. Scotty in particular has a hard time with the local slang.
Naturally Kirk and the others are not going to take their captivity lying down. In a classic scene, Kirk taunts the guards until they let him teach them the card game "fizzbin", which he makes up on the fly. The guards are concentrating so hard on the rules that they don't even notice that he contradicts his own rules several times. When they are thoroughly confused, the three Starfleet men quickly and easily neutralize them and escape.
Spock and McCoy head to the local radio station to contact the Enterprise. Their mission: to see if the ship's computers have any suggested course of action for how to correct the current direction and organization of the native society. It's a laughable idea that a computer could somehow analyze such a complex and nebulous situation, but we know the Enterprise's computer has amazing abilities. Even so, the computer finds no solution.
Kirk intends to head back to Oxmyx's headquarters, but gets picked up by Krako's men on the way; Krako is Oxmyx's main rival. Krako wants to make a similar arms deal with Kirk, although he's willing to cut Kirk in for a piece of the action to sweeten the deal. Yet again Kirk refuses and yet again he's put "on ice".
Oxmyx calls Spock and tells them of Kirk's capture, but offers to help Spock free Kirk. With no choice, Spock and McCoy beam back down, only to be captured by Oxmyx again. However, Kirk has escaped from Krako's men and takes over Oxmyx's headquarters with a stolen tommy gun.
Spock informs Kirk of the computer's failure to provide a course of action, which frees Kirk to wing it. He steals clothes from Oxmyx's men for him and Spock - and they sure do look smashing in the pin-stripe suits and period hats. They head back to Krako's headquarters in a car, which contains another classic scene of Kirk trying to drive a car and Spock trying to survive riding in it.
They contrive to enter Krako's headquarters with the help of a young boy who will create a diversion for them to get close. This is a very dubious idea at best - we have seen how violent the mobsters are. How can responsible Starfleet officers risk the life of a child in this way? Nevertheless, they get into Krako's headquarters and have Scotty beam him to the Enterprise to wait.
They return to Oxmyx's headquarter so that Kirk can put his plan into operation: the Federation is taking over and becoming the "big boss", so Kirk is just going to get everyone organized. Oxmyx calls various bosses on the phone, and Scotty beams them to Oxmyx's headquarters. Soon all the major players are there. Kirk says the Federation wants them to get organized and make a profit, since the Federation's cut will be 40%.
Doubts arise among the bosses, however, since they have only seen a few Starfleet men - how do they know the Federation is so powerful? Meanwhile, Krako's men arrive outside and begin shooting it out with Oxmyx's defenses. Kirk has the Enterprise use ship's phasers to stun everyone in a 1-block radius around them. This silences all doubts.
Kirk puts Oxmyx in charge, with Krako has his second-in-command. He warns them all not to make trouble, because the Federation will be back every year for their cut. They return to the Enterprise.
Spock expresses some discomfort with Kirk's actions on the planet, but Kirk says the Federation's cut will be used to guide the planet back into a more normal line of development. McCoy realizes he left his communicator back on the planet, and Kirk and Spock razz him about how the natives will soon be at the Federation's level of technology as a result!
This episode was obviously designed for laughs, and it's mostly successful. The characters' confusion with the local slang was amusing, and just when it started getting old, Kirk starts using it, which makes it funny again.
Spock's reactions to the various situations was also amusing. With the game of fizzbin, he obviously doesn't realize what Kirk's doing at first and tries to correct what he perceives as misinformation. Once he catches on, he's careful not to spoil things, but he doesn't lie, either. Later, he obviously knows Kirk is trying to beat the locals at their own game by adopting the local clothes and speech, but he just doesn't quite get it, which is funny.
Beyond the fish-out-of-water humor, this episode is essentially fluff. In some ways, this is too bad, because the premise is interesting. We've heard a lot about the Prime Directive, so it could be fascinating to see the result on a planet of not following the Prime Directive. In fact, I can almost imagine someone from the planet reading the mob history book and deciding it would be useful to bolster his ambitions; but I can't believe that so many people on the planet would just "imitate" the book. Human society today (and in the 1920s when the mobs were prevalent) considers mob rule to be morally wrong, so why don't the natives think that? Were they so awed by the Horizon that they think that anything it left behind must be good?
For that matter, why would the Horizon have that fancy-bound copy of a mob history book on board anyway, let alone leave it behind when they left? This plot device renders the episode essentially meaningless.
There are some logical inconsistencies in the episode, as well. Oxmyx is the biggest boss in the world, and yet hits on him and by him consist of a handful of men with machine guns. He's got the largest territory, and yet he splits control of the city with Krako, which doesn't make sense. The main characters also do a lot of running back and forth and not getting anywhere, which seems unnecessary.
In the end, Kirk hasn't done much to change the situation on the planet. Presumably his intention is for the Federation to send people to pull the strings now that the Federation is in charge. In the meantime, I don't see why the power structure on the planet wouldn't just revert to what it was before, with the bosses fighting amongst themselves.
Overall, this episode is good for a laugh, but isn't very meaningful.