Forgive me, but I’ll be drawing mostly from the prequels here. The Clone Wars were alright, though, and I’ll fight you on that.
Anakin Skywalker was born a slave on the Outer Rim of the galaxy, where he stared at the sky every night and dreamed of an adventure. He dreamed of a life beyond his dismal situation, where he could save himself and his mother from a life of labor for the profit of others. Despite being a slave child, Anakin managed to find the time and space to cobble together a protocol droid from the heaps of machine scraps surrounding his home. He uses his mechanical genius to actually earn a small living for himself on the side, and he becomes both the youngest and only human – it’s a reflexes/number of arms/brains/whatever thing – podracer on Tatooine.
One day, a ship crashes on Tatooine, and Anakin offers his help, but he comes up with bad news; their hyperdrive is shot, and the price for a new one is too high to reach. Luckily, there’s a podrace coming up, and the prize money is enough to get them off the planet. Anakin wants to help these people, but he has a few other motives. He’d very much like to escape with them (and the girl he’s developed a crush on), and helping these powerful people out is likely to earn him some favor.
He succeeds, and though he doesn’t get to save his mom, Anakin earns his adventure with the Jedi. After some other boring prequel stuff and a pretty sweet lightsaber duel, Anakin becomes apprentice to Obi-wan Kenobi. They’re close enough in age and talent that they practically train each other. Over the course of the Clone Wars, they become the youngest generals in the entire army, and their skill in battle is arguably greater than plenty of the Jedi Council.
It’s not all good for Anakin, though. Ignoring the whole Darth Vader thing for a minute, the Jedi Code doesn’t exactly mesh well with Anakin’s goals. Most Jedi were picked up as infants, and he’s had time to develop his idea of himself before the Jedi indoctrination. He ends up marrying that girl he met on Tatooine, which is a big no-no for the Jedi. He also is pretty emotional, and has a sense of independence that has usually been trained out of a Jedi.
Up to this point, there are some hints of gangster that shine through in Anakin’s story. He’s a poor kid who dreams of a better life and legacy, and he’s got the raw talent and the force of personality to make it happen. He sees opportunities where they come to him – his mechanic side-business – and he makes them when he needs to – offering to race for the crashed Jedi. Though it’s difficult to call the ladder Anakin begins climbing crooked, it certainly isn’t straight; for most of their history, the Jedi have operated based on an internal authority and the Jedi Code. Still, Anakin sees through their enlightenment hypocrisy, and breaks the rules as he sees fit. No emotional attachments? Nearly every prominent Jedi has, in some part of the Star Wars universe, a relationship, but over and over again, they scold Anakin for his righteous anger and his determination. Anakin becomes disillusioned and afraid, and starts looking for ways to secure his future outside of the Jedi.
By this point, Anakin has found a mentor in Chancellor Palpatine, who is secretly the Dark Lord of the Sith. He represents everything the supposedly fight against, but Anakin doesn’t know that yet. All he knows it that Palpatine disagrees with the Jedi in all the same places as him, and he eventually offers him another path: a new code.
Another weak point of the prequels is that Anakin’s fall to the dark side becomes rushed, as if they forgot he was Vader until the last bits of the trilogy. This makes it difficult to map his transition to Vader in a gangster light, but his biggest reason for doing so is his desire to protect himself, his wife, and the life outside of the Jedi that he has built for them. It seems unreasonable to say that its enough to turn to the dark side over that, but there is more gangster flavor to be found in the Code of the Sith:
Peace is a lie, there is only passion.
Through passion, I gain strength.
Through strength, I gain power.
Through power, I gain victory.
Through victory, my chains are broken.
The Force shall free me.
This isn’t a perfect match, but this is a good picture of one possible routes up the crooked ladder, especially when viewed against the relatively straight ladder of the Jedi:
There is no emotion, there is peace.
There is no ignorance, there is knowledge.
There is no passion, there is serenity.
There is no chaos, there is harmony.
There is no death, there is the Force.
The Jedi stood for law and order for its own sake, and the Sith fought for personal power and for personal freedom. Their methods were often objectionable, and they frequently abused the weak, but within their own, there was a certain level of protection, as long as you maintained your power. Anakin saw the chaos and death inherent to the Jedi; he was one of their greatest generals in the war. When they threatened his love, he refused to give up his emotion for the false peace of the Jedi, and instead gave into the dark side, with all its costs.
The beginning of his story can be seen as an O’Kanian story: as a slave on Tatooine, he was forced to work for hours on end to merely survive, and at times, it was not entirely certain that their slave wages would enable even that. When the chance comes, Anakin has to cling to it in hopes of making life better for himself and his mother. The Jedi were on their way out; the Republic no longer needed them, and the grey morality inherent to their order was no longer necessary. Again, it’s difficult to call this ladder crooked, but it’s no easier to call it straight, with enough analysis.
The ladder of the Jedi, despite the lip service they pay to the greater good of society, is not entirely straight. It lies in an uncanny valley where it shares some parts of both. It is outside society, and its methods are strangely cruel. It obeys its own code, entirely separate from the law laid down by government. At the same time, parts of that code are far stricter than the law, and the Jedi can be seen as hyperlegal, but only in ways that support their isolated society.
In a Lupshavian sense, it’s a bit easier to read Anakin’s story as a gangster’s. His disillusionment with society starts young, as it’s not difficult to recognize the hypocrisy and evil of slavery. Initially, he sees the Jedi as an escape: heroes of the Republic who stand against evil wherever it can be found. However, as he grows more familiar with the organization, he sees more and more of the contradiction built into the Code. Anakin is able to do this partially because of his relative old age of induction into the Order; it allowed him to develop his own values, which often align with those discussed by Lupsha. Independence, freedom of action, and individualism are all impossibilities for those who strictly follow the Jedi Code. They forbid attachments as well, and would likely see emotional attachment as materialism, another value. It’s also difficult to deny that the Jedi don’t really look very cool, besides the lightsabers. Darth Vader looks awesome, and though the Sith likely would disagree, there’s a degree of materialism in the conquest demanded by their interpretation of the Code of the Sith.
Despite the good in his heart, Anakin frequently chose to make the wrong decision, and was often punished for making the right one. As he grew tired of the hypocrisy of the code he and his friends followed, he found a different code from the Sith. That code allowed Anakin to achieve his goals, thoroughly outside of the law. Had he continued on the comparatively straight ladder of the Jedi, he would have been unable to live his life as he saw fit. Anakin defied the Jedi’s law against attachment, and took the crooked ladder of the Sith.