Now that they had defeated the Mandalorians, taken their vacation, and had breakfast, Revan and Malak decided out of boredom to go to the dark side…
As foolish as that sentence sounds, most of the fiction I have read where characters go to the dark side has as much rhyme or reason. Regardless of who we use as an example, there were logical even good reasons why they did so.

RAKATA: The Rakata had the same problem every Imperial race has ever had. ‘We’re better than anyone else, so what we think is more important’. Slavery conquest, hey, if we want to it’s all right. Every Earth Empire went through that phase. Whether you use the ‘Divine Right of Kings’ ‘Historical Imperative’ or ‘Manifest destiny’, it boils down to ‘we’re right, and you have to accept it’.

Their fall was predestined just like any such empire. Too powerful to attack from without, they were destroyed by their own factionalism. In KOTOR, the Rakatan computer said that factions arose, destroying them from within.

REVAN AND MALAK: The specifics of how this pair fell are vague, but there are enough implications to explain what occurred. First, the Jedi entered a war already 16 years old if you go by what Canderous said, and the Jedi had been part of it for only four years. So let’s take the segments of this war in sequence.

MANDALORIANS VERSUS OUTER RIM: The Mandalorians began their war by occupying a number of the planets of the Outer Rim. This according to Canderous was their way of testing the waters, not unlike the German’s occupying the old ancestral lands that led to WWII. They were seeing how far they could push the Republic. Like the ‘Allies’ of WWII, nothing was done, but this period lasted 16 years instead of the four before Germany invaded Poland.

Now look at it from the view of the young Jedi. They are watching this happen. The Republic and their own council do nothing. Why not? The Council is of course outside of politics, but the Padawans could see the literal blindness of the Senate. I looked at this in my own work, and figured the following:

The senate didn’t care about those nations beyond their borders. After all, they had probably tried to get them to join the Republic. They had ignored the offer, so it was their own damn fault that it was happening. You snooze you lose. Besides, they would have needed to convince their constituency that such a war was necessary.

So they waited, expecting the Mandalorians to attack them, but like the US right before WWII, knowing the Japanese are going to attack, they assumed the attack would be less efficient than it was.

THE WAR BEFORE THE JEDI; This period is why I comment constantly on the incompetence of the Republic Military, and why Canderous expected to win. It wasn’t the average fighting man who was incompetent; it was the officers leading them. The only historical armies that match the Republic at this were the Nationalist Chinese army of WWII or the officers of the Army of South Vietnam. The average man in both armies were fierce fighters who fought valiantly, even as their officers sold their rations and ammunition to the black market to line their own pockets.

HOW THE PADAWANS LOOKED AT IT: We have the idea that the Jedi were trained to consider the Republic the most important part of their lives. But at what point do you ignore the people of that body? The Padawan would have been torn by this dichotomy; which is more important, the 11 million citizens of New York, or the government of that city? If you were a soldier, and your orders were to abandon those millions so the Mayor could escape, what would you do?

THE JEDI IN THE WAR: As I commented in my own work, the Jedi were facing three wars when they marched to war. They were fighting the Senate, the military high command they were supplanting, and only then the Mandalorians. This is what I think finally drove Revan and those who followed her into open rebellion. If the Jedi Council would not support them, the government is corrupt, then there was no reason for them to give obedience to either body.

Jorus C’Boath: The senior Jedi in command of the Outbound Flight expedition, the first we heard of him was of his clone, a dark master who controlled the Emperor’s secret storehouse on Wayland. The original C’Boath was a Jedi who believed that being a Jedi made you automatically wiser than other people. He didn’t show his complete hubris until the Outbound Flight mission was launched however.

When it had, he first took control of the legal system then the mission itself. Instead of waiting as the Jedi had for centuries for children to be presented, he had the Jedi actively looking for youngsters with Jedi gifts forcibly removing them from their families for training.

The mission was attacked by a combination of the Trade Federation, and the Chiss, the Trade Federation’s droid fighters controlled and commanded by Admiral Thrawn. At the height of the attack, his mission under attack, thousands dead. C’Boath went to the dark side, reaching across space to throttle Thrawn.

However swift action by Palpatine’s agent struck the final blow to save Thrawn’s live and kill most of the survivors.

COUNT DOOKU: The count when you think about it craved order. He had left the Jedi because the Council was unwilling to convince the Jedi Council that they could mitigate the problems caused by the bureaucrats in the Senate. However the only way the Jedi could have done this would have been to take control of that government and settle all of the disputes directly. When you think about this, even if they had wanted to the Jedi could not have done it. It would have reduced them to feudal lords administering vast sectors of the Republic, spread them thinly through the galaxy, and stopped them from even attempting to teach new apprentices. Dooku from the sound of it was the kind of man who wanted it right now, even if it can’t be done. So he left the order, returned home, assumed his ancestral title, and brooded.

How he came to meet Sidious, and how he became the Sith Lord’s apprentice is not known. But the reason is clear if you have read the previous paragraph. Sidious wanted to remove the power from the Senate, and probably for the same reasons that Dooku did. But in a democracy you need to follow their own rules to hamstring them. Like the rule used in The Phantom Menace where the importance of Naboo’s occupation was superceded by senatorial procedure. As much as it hurt the Republic to lose Valorum, it hurt even more that by using that procedural rule, Palpatine was able to thrust himself into power.

However Dooku was still trying to get the Jedi to do what he wanted. If he could have convinced Obi Wan that there was a Sith Lord inside the Senate, it would have caused what is called a ‘mole hunt’, the term used in Intelligence agencies when they believe an enemy agent or ‘mole’ has infiltrated. The war that was to occur could have waited then, because the restructuring of the Senate would have followed as being after being was investigated and interrogated. They might not have even needed the war to create the democratic equivalent of an Empire. Look at Germany not long after Hitler took power, and look at our own US now. Rules created to limit the freedoms of the people until there is no longer freedom, only ‘safety’.

One point of importance is that even as they were fighting, Dooku still tried to convert Jedi if he faced them one to one. If they didn’t, of course they died. In one book Dark Rendevous, Dooku even tried to convert Yoda to the dark side. But his arguments paled beside our next fallen.

Asajj Ventress: A native of the planet Rattatak, she had been orphaned when her parents were killed by a warlord named Osika Kirske. A stranded Jedi Master named Ky Narec rescued her. How Narec ended up on that world was never really explained. Whether his ship was shot down or crashed was never said. Dooku claimed that Mace Windu had sent him then abandoned him. This claim was made primarily to infuriate Verntress.

What is known is that Narec taught Ventress until his death at the hands of the same Osika Kirske. Ventress led a rebellion, killing a dozen more of the warlords after first dispatching Osika Kirske and became a political power on her world.

When Dooku held a competition on Rattatak Ventress impressed him enough that he accepted her as a commander, but not as an apprentice. Because she had been told the Jedi had abandoned her master, she focused her hatred on them, killing them wherever possible, even going so far as to bounties on 85 senior Jedi. The one time she actually spoke to Jedi rather than at Jedi was during the same mission outlined in Dark Jedi. Her arguments to the two young Padawan was far more cogent than those used later by Dooku.

DARTH VADER: Vader’s fall was obvious. He felt love for two people, his mother and his wife. His reaction to the death of his mother pretty much gave us an idea of what would happen later. Anyone willing to slaughter an entire tribe of Tusken Raiders for his mother’s death foretold what would happen if Padme were in danger.

But it also showed us the fallacy of Yoda’s ‘go to the dark side and never go back’ statement. That same love extended to Luke caused Vader to attack his master, and save his son

MARA JADE: Mara is an example of the old saw, ‘as the twig is bent’. She had been trained directly by the Emperor, but her capabilities stunted. He didn’t want another apprentice, he wanted someone trained sufficiently to be his sneak and assassin, but not well enough to challenge Vader.

However when Mara was faced the clone of Luke Skwalker, she broke that chain and freed herself.

KYP DURRON: Kyp had a lot of reasons to hate the Empire. His parents and he had been sent to Kessel where they died. His brother had disappeared into the Imperial Military, and when Kyp was suborned by the spirit of Exar Kun, that was the hook Kun had.

Durron plundered the mind of Qui Xux, discovering everything he could about the super weapons she had created and used the Sun Crusher to attack Admiral Daala, then the planet Carida, the primary training facility for the Empire. This was all to gain revenge for the deaths of his parents and older brother.

But cruel fate took a hand. After Durron had fired a torpedo into Carida’s sun, he discovered that his brother was still alive on Carida. With bare minutes before the sun would nova, he tried to rescue his brother, only to have him die minutes from escape.

There are others I could mention, even Luke Skywalker briefly walked on the dark side thanks to the clone of the Emperor.

So yes, kiddies, there are reasons to go to the Dark Side. Just make sure they are good ones.