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I have been playing chess practically all of my life but during phases, I would play a lot for a couple of months and then spend a whole year without playing.

Right now I am in one of those phases but I am determined to stick with it and really improve so I have been taking on tactics and end game studying but my Achilles heel has always been the opening theory.

I really like to play the Sicilian defense, in particular the Dragon and have a couple of books on it but there are so many different replies and variations after 1. ..., c5 that going this route seems like an impossible undertaking, I've even read somewhere about the "Sicilian Jungle", and I've had a few bad experiences when trying to force a Dragon-like structure without considering white's responses.

So my question is; considering white's most common responses to the first couple of moves, which variations are the ones the would be more beneficial to begin this training and that can help limit white's options?

Thank you.

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    I hope you find a good answer to this, but my instinct says that you won't. The Sicilian is perhaps the single most notoriously deep opening of all, and if there were solid lines for Black that could easily reduce its initial complexity, I'm sure we would have heard of them by now! – Henry Keiter Dec 1 '14 at 17:06
  • I agree with @HenryKeiter. The Sicilian is very vast. – Wes Dec 3 '14 at 15:49
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There actually is one (semi-respectable) sicilian, that really cuts down on white's options: The Nimzo-Sicilian. The Nimzo-Sicilian is characterised by the moves 1.e4 c5 2.Nf3 Nf6!? Now 3.d4 hangs the e4 pawn … you will encounter that a lot in blitz. After 3.Nc3 there is 3…d5 leaving the usual sicilian structures behind. After 3.e5 you play 3…Nd5, where play can transpose to the Alapin. The very sharp mainline is a pawnsac 1.e4 c5 2.Nf3 Nf6 3.e5 Nd5 4.Nc3 e6 5.Nd5 ed 6.d4 Nc6 7.dc Bc5 8.Qd5 Qb6 … After 1.e4 c5 2.Nc3 you have to play 2…e6 first. Here you can chose to go for a number of variations, maybe the Kan is actually a good choice. But you have to realise that 2.Nc3 is already a concession by white: Even the accelerated dragon is now better than after 2.Nf3.

Now this seems like a pile of variations already, so what did you actually gain? - No Bb5-variations (and you could still transpose to the Sveshnikov!). - No Maroczy-bind: Which is a nice way to play against the Kan via 1.e4 c5 2.Nf3 e6 3.c4 ... - The GrandPrix-Attack (1.e4 c5 2.Nc3 …3.f4) is not as strong as against 2.d6 (because you are ready to play d5 in one move). - You can play the same move against the Alapin (2.c3 Nf6). - The Nimzo-Sicilian is very rare, so usually your opponents won't have much of a clue about it.

So why doesn't anybody play it? In the pawnsac-mainline the current theoretical assessment is a worse endgame for black, that probably deters GMs. But to get there white has to survive several tactical shots with a king in the middle of the board and playing this mainline isn't even forced for black!

I have played it for years and it usually leads to an open fight, where both sides are quickly out of book (my opponent, because the variation is so rare, and I, because I'm to lazy to prepare). To me the Nimzo Sicilian is also an transposition paradise: You can cut out a lot of options for your opponent and still often reach the Kan or Sveshnikov. It is also a pain for Bb5 or Maroczy-players, because they suddenly realise that they didn't actually solve their "sicilian problem".

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    I don't understand what the advantage is, for Black, to transpose into an Alapin rather than playing against the open Sicilian, at this point. Also, after 3.Nc3 d5 you must really know a whole lot of theory about the 3...d5 positions. – gented Jan 1 '18 at 19:51
  • Personally (a Najdorf player), if I am playing the Sicilian I am rather looking for something wild than for playing a boring Alapin... – user1583209 Jan 1 '18 at 20:23
  • Same here: if I play the Najdorf (or any other system) is because I want to play it. Otherwise just go 1.e4 e5 and take it from there. – gented Jan 2 '18 at 14:27
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Look I would like to categorize the Sicilian opening and I believe that after reading this you should feel somewhat comfortable.

  • First you must avoid Sicilian Dragon when you are new to the Sicilian. The Dragon requires a lot of extra courage to play and because White's K-side attack is just too fast black somewhat fumbles in the opening itself if he does not know how to counterattack. Black's g6 pawn can be hooked early by White for tearing the K-side attack.
  • Second Sicilian Kan/Najdorf/Scheveningien/Richter-rauzer/Taimanov are kind of transposable. If you are playing this line then you ought to know all the above variations. There are lot of exceptions to these though but they can be ignored as of now . In majority of the Vast games played in the above line the basic principle if that black will attack in the Q-side and in the center & black needs to stall White's attack in the K-side. If black has that dare then only he should attempt these lines .
  • Third the best Sicilian to start with is Sveshnikov. It removes the complexity and does not need sharp opening theory. It is easy to understand and black can have a good fair game. Most important is that it an entirely different line and Sicilian Pelikan is one more branch of this line. Black can choose this opening and white cannot transpose it into any other Sicilian opening.
  • Fourth you should be aware of some other Sicilians also like Rossolimo/Alapin/Smith Morra/Grandprix Attack. Actually these lines depend upon white what he would play in the second or third move and Black cannot avoid the opening knowledge preparation. So these lines are indispensable.
  • Fifth if you want to know the Najdorf kind of Sicilian then try understanding the Scheveningien. It is the best and it will give you the entire insight of Sicilian games as a whole.
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Alas, the Sicilian is not an opening for the faint of heart. It strives to exploit the complexity and dynamic nature of the position, so it is quite hard to find shallow solutions. At risk of avoiding your question, I would say that it is best, if you want to avoid theory, to pick up a line more alike the open game. Still, I did my best to show a nice plan.

First, lets handle the move 2 anti-Sicilians (2. c3). In general, they are in fact designed to reduce complexity, so a small bit of knowledge can go a long way. Against 2. Nc3, you should continue with the move that you use against 2. Nf3. The closed Sicilian is a relatively complex opening still, but I find that up until 2000 USCF (or 1800 FIDE), Closed Sicilian players do not have a grasp of theory, so you can likely be safe to skim on that section of your study.

Against the Alapin Sicilian, the general recommendation is 2... Nf6. However, I think the line 2... e6 is underrated, so you may be able to use it to avoid theory. After all, particulars have to be studied individually. It is recommendable to find a personal line that is intuitive, but your general idea is to play d5.

For a generic solution against the open Sicilian 2. Nf3, you will want to avoid playing the Najdorf at least as every chess player and there grandmother has a way to play against it. Your try of using a Dragon-esque system was likely difficult as it is a highly theoretical variation and even then, semi-dubious. In addition, it seems troubling to play any line starting with 2... Nc6 due to the Rossolimo and the very sharp nature of the lines here.

My recommendation has to be the Kan variation (2... e6 3. d4 cxd4 4. Nxd4 a6). While it can be a bit difficult to learn, it is one of the less sharp lines and it is seldom studied by lower rated players. I would try playing around in some relatively short games and seeing where you falter. There is plenty of material on the specifics of the Kan variation, but the general idea is to play Nf6, d6, Be7, O-O, Nbd7, and Re8. This sort of "hedgehog" style position gives plenty of opportunity to both sides and should not require too much theoretical knowledge.

Good luck :)

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    It would be helpful for us non-experts to give actual moves (like 2.c3 in this case) because some of us don't know all the variations by name, even if they're spelled right! – bof Dec 3 '14 at 1:15
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Sicilian is a good opening and it is double edged. Unless I read books, I was not able to play with anyone. I guess Richter-Rauzer is missed in the previous comments, which is possibly a part of open Sicilian I presume

[FEN ""]

1.e4 c5 2.Nf3 Nc6 3.d4 cxd4 4.Nxd4 Nf6 5.Nc3 d6 6.Bg5 e6 7.Qd2 a6 8.O-O-O Bd7 9.f4 h6 10.Bh4 Be7 11.Be2 Qc7 12.Bf2 Rc8 13.Nb3 b5 14.Bf3 Na5 15.Nxa5 Qxa5 16.Kb1 b4 17.Ne2 e5 18.Nc1 O-O

It is fun to play it.

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The dragon indeed requires remembering many sharp lines. Try the hedgehog formation . Play early a6 and e6 to limit white possibilities. I personally play this and i don't remember any lines just general ideas key squares maneuvers e.t.c
It works well against virtually anything white might play (maybe excluding 2. c3 )

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