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After answering this question, I came up with my own. What if Palpatine/Sidious had allowed Anakin to complete his Jedi training before trying to tempt him to the Dark side? Then I realized that, had Anakin gone through the normal training process and legitimately become a Jedi Master, he would have likely been "indoctrinated" and would have internalized many of the ideals of the Jedi Order, which would have made it much more difficult to sway him (it's much harder to kill a personally held ideal than to tear down a belief you are being taught and haven't yet committed to your own set of morality).

So, this brings me to the crux of my question: How many fully trained Jedi have been tempted away from the Light side of the Force to become Sith? Jedi who have attained the rank of Master would really be the only ones that "count" for this specific question, as even Jedi Knights may not have yet become fully invested in the Jedi Order. In the movies, we see Count Dooku as having been a Jedi Master (and even a respected instructor in the Jedi Temple) who fell to the Dark side after having his faith in the Jedi Order shaken.

I'm not familiar enough with the EU myself, but I would assume that, if he was able to be so "easily" drawn away from something to which he had devoted seventy years of his life (from the linked Wookieepedia article), Darth Tyranus was likely not the first Sith to be "recruited" from the upper echelons of the Jedi Order. Are there other Jedi Masters in canon that are known to have changed their allegiance so drastically?

EDIT: I've seen this question that talks about Jedi leaving the Order, but that doesn't quite get at the heart of what I'm asking here.

I also read this question about coming back from the Dark side, but it doesn't specifically address how many actual Jedi Masters have been plucked out of the hallowed halls of the Jedi Temple and cast into the dark and twisted world of the Sith.

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    Not an answer, but being Jedi or Sith is much like a belief in a religion or political affiliation here in real life. People are constantly shifting in their ideas as they experience life. The more powerful the evidence or experience, the faster they move towards a new belief. This is why monks and nuns tend to live isolated, so as not to stray from their belief through life experiences (and that might not even be enough). A life-altering event tends to sway people quickly, such as "miracles," while most people slowly drift to an ideal by gradually increasing tolerance. – phyrfox Aug 11 '14 at 22:37
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    Normally I would close this as a list question, but I imagine this is a very finite list, even if Jason's answer doesn't already cover everything. Just making this comment to let everyone else know I don't feel this warrants closing, in the hopes people share my opinions. – James Sheridan Aug 12 '14 at 1:56
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Canon - 1 or 2

In the Disney-approved Star Wars canon, the only one we're absolutely sure of is Count Dooku. We'll have to wait and see if the new movies introduce any more.

  • Master Pong Krell, who appears in The Clone Wars animated series, is an interesting near-miss. Krell was a Jedi Master who wanted to become Dooku's apprentice during the Clone Wars, but he was never able to; he was killed by clone troopers while attempting to sabotage a Republic offensive, intending to gain Dooku's favour.

A second that may count, depending on your perspective on Sith-ness, is Quinlan Vos. Vos falls to the Dark Side in the canon novel Dark Disciple, and allies himself with Dooku in a quasi-partner, quasi-apprentice kind of way. It's not entirely clear whether or not to consider him a Sith, but Dooku at least entertains the notion:

[Y]ou could join with me again. We will defeat Sidious together!"

"I won’t be your apprentice!" Vos started to choke Dooku again.

"No, no!" Dooku wheezed. "A team. Equals."

"Sith don't work that way."

"Are you and I ordinary Sith?"

Dark Disciple Chapter 36

Legends - 7 to 14

Wookieepedia has a list of Dark Jedi who also became Sith, so this seems like a good place to start. According to that list, there are seven individuals who are explicitly identified as being Jedi Masters before defecting, but possible as many as 14 fit your criteria:

Confirmed:

  1. Darth Desolous, from The Force Unleashed game
  2. Skere Kaan, who gets mentioned in a few books and comics
  3. Darth Krayt, with a ton of appearances in comics
  4. Ajunta Pall, from the KOTOR games
  5. Darth Ruin, who comes up in some of the prequel novelizations1
  6. Count Dooku
  7. Kalatosh Zavros, from The Old Republic MMO.

There are also loads who are just described as "members of the Jedi Order" (XoXaan, for instance), who may or may not have been Masters.

Questionable:

  • Darth Traya, from KOTOR2, was a Jedi Master who was exiled for her teachings, which were deemed to have caused the fall of other students and led to a lot of Jedi being killed (and setting off the events of KOTOR1). She didn't fall until some time later, and even then she wasn't a typical Sith; she rejected the label herself, despite controlling the remains of Revan's Sith empire, and she was more interested in destroying the Force itself, rather than the schemes of galactic domination and/or wiping out the Jedi typical of other Darths. However, she did use the "Darth" moniker herself, so she's kind of ambiguous.
  • Barel Ovair and his family, who are mentioned in the prequel web-series for The Old Republic MMO. Ovair is special because his family was sent by the Sith Empire to infiltrate and spy on the Jedi Order, so he was already a Sith when he became a Master. Wookieepedia has entries for Ovair, his father and his grandfather, who were all in the same boat. Only Barel is explicitly said to have been a Master, although it seems likely that his predecessors reached the rank as well.
  • Sora Bulq. Sora is special because he was never officially a Sith; Count Dooku wasn't allowed to have an apprentice because of the Rule of Two, but he got around that by creating the "Dark Acolytes", of which Sora was one. Whether or not you count him depends on if you consider these Acolytes to be part of the Sith, even if they're not officially Sith.
  • Quinlan Vos, another of Dooku's Dark Acolytes. Quinlan was ostensibly a Jedi infiltrator in Dooku's ranks, but it's left ambiguous whether he was just staying undercover, or if he fell and was later redeemed. He certainly did some very nasty things, but he was also uncharacteristically (for a Sith) helpful to many Jedi he crossed paths with during that period
  • Luke Skywalker himself. Luke fell to the Dark Side during the Dark Empire comic book series, which involve Emperor Palpatine being reborn in a clone body2. Luke, who by this point is calling himself a Jedi Master, plans to pretend to defect so that he can get close enough to kill the new Emperor, but he instead falls to the Dark Side for real and becomes Palpatine's apprentice3. Whether you think this counts depends on whether or not you accept Luke's self-styling as a Master. Thanks to bitmask for reminding me of this case.

1 Although Ruin is first mentioned in the Phantom Menace novelization, which is canon, he isn't identified as a former Jedi Master in that work, hence why he lives in the "Legends" category.

2 Because coming up with original villains is so hard you guys

3 This sounds familiar

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    I doubt that list is complete, myself. I'd be seriously surprised if Darth Caedus, for example, wasn't a Master by the time he became a Sith. Good start though, but you should probably edit it to include others. – James Sheridan Aug 12 '14 at 1:58
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    Caedus actually was not (I looked it up, he left the Jedi for a while before he could be promoted, and then he fell), but you're right that there were some grey areas not covered in that list. I've now added them – Jason Baker Aug 12 '14 at 2:53
  • Wasn't Quinlan a double agent / spy, though? – Shisa Aug 12 '14 at 6:24
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    Originally yes, but it's ambiguous whether or not he fell for real while on his mission. He certainly did some damned distasteful things under Dooku's orders, to the point where almost all of the Jedi thought he'd fallen, but he also told Aayla Secura that he hadn't, and helped both her and Obi-Wan when he could easily have killed them. I've updated my answer with clarifying details – Jason Baker Aug 12 '14 at 7:02
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    @jliv902 I considered it, but I decided to limit my list to Jedi who actually joined and self-identified as one of the Sith. I consider Atris to be a Dark Jedi, because she was never affiliated with a Sith Empire, and did not consider herself to be Sith. Asking what Jedi just fell to the Dark Side is, in my mind, beyond the scope of this question – Jason Baker Sep 4 '14 at 22:17
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The Lost Twenty provides an approximate upper bound of 20 up to the time of the Clone Wars (Count Dooku was the 20th). These are the Jedi Masters officially acknowledged by the Jedi Order as having resigned their commission and left the Order over ideological differences (such as joining the Sith). Not all 20 necessarily left to join the Sith so it's only an upper bound, and it's not clear if this comprises the entire history of the Order so it's not an absolute upper bound.

  • This only covers Jedi who announced that they were leaving. Presumably a Sith wouldn't necessarily do that. – Brendan Long Feb 18 '15 at 8:56

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