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Anakin started off as a Jedi and then migrate over to the Dark Side. Why can't he be a master of both and become the greatest practitioner of the Force?

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The Jedi and the Sith both use the same Force. Using the force requires the same skills and sensitivity, regardless of whether you adhere to the dark or light sides. In terms of raw force affinity, a light-sider doesn't have any capabilities that a dark-sider doesn't, and vice-versa.

So, if there's no difference in ability, why are light side and dark side they separate? Well, because the dark and light sides are different philosophies and sets of values. A light-side force user will act differently to a dark-side one, not because the light-sider and dark-sider have inherently different force capabilities, but because they have different values and so pursue different ends by different means. Because the two philosophies are opposed in multiple respects, it is impossible for a single individual to adhere to both the light-side and dark-side philosophies simultaneously. (I guess technically someone could come up with a "grey side" hybrid philosophy with features of both, but that would be a new thing rather than light-side or dark-side. Reformed Orthodox Jedi-ism, perhaps.)

That said, some force techniques have been described as "light-side" or "dark-side" techniques. This indicates that these techniques either require belief in and self-identification with aspects of one of the two philosophies ("Force lighting torture is justifiable self-defence!"). As a consequence, using a dark-side technique requires a force user to adhere to and believe in the dark side's ideals and ethics, at least in part; The same is true for light-side techniques and believing in light-side philosophy.

tl;dr: Mastering both the dark side and light side is meaningless because A) They're not separate or complimentary skillsets in the first place, and B) You can't want to use both at the same time.

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    There is indeed a grey side. IIRC, there's a case in the EU of a Jedi that learnt Sith techniques but didn't use them for evil. Or something of that kind. Anyway, I don't think there's any case of a grey Jedi in the Disney Canon. Dec 16, 2015 at 7:48
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    Love the "Reformed Orthodox Jedi-ism" +1
    – Burgi
    Dec 16, 2015 at 10:15
  • Sorry, this answer is canonically wrong. They differ in how they access the Force, not just in abstract intentions. Dec 16, 2015 at 15:02
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    @DVK How so? They both use midichlorians, just one intends to use the Force to meet their ends while the other asks nicely.
    – user40790
    Dec 16, 2015 at 16:54
  • @Axelrod - the details are much different. Novelizations and other books cover this in detail. Dec 16, 2015 at 17:13

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