Why play the Classical Sicilian

After about 2 years of study and lurking on this forum... after much consideration (months of just thinking about the opening), and alot of experimentation... I finally know, with full confidence, which Sicilian I am settled on. So here I am, sharing this analysis. Why? Well... I want to write down my conclusions in a capstone summary. It seems appropriate given the amount of time I've put into this game. Beginners can benefit from reading my analysis, even if they don't agree with the conclusions. It'll be a long post, so if you don't want to read it go ahead and TLDR.

So in choosing a repertoire I wanted to satisfy a few criteria: 
- since it will primary be played in an online setting it should have some surprise factor to it. It should at least be somewhat uncommon. If its rich and provides room for interesting deviations, even better
- black should have "control" of the game - i.e. it's black who primarily chooses which lines to enter
- it should require precision from the opponent early, and be punishing of mistakes 
- it should be solid in the event the opponent knows it, or so obscure we can assume they won't
- playing equal positions as white, or -0.30ish positions as black, is fine... so long as there are other forms of compensation
- we can assume the repertoire is not directed at GM-level opponents

So I'm pretty set on the Classical Sicilian at this point. But firstly, why the sicilian? Well, the sicilian is the only serious 1. e4 defense where black has primary control of the game. Black can choose from 13 or 14 mainline sicilians, and white has a very hard time dealing with all the theory. The sicilian is also complex in a way where it never gets old or played out. It's very rich. If you want to deviate you can do that. If you want to play it in a particular style (tactical, positional, theoretical, obscure), you can do that. Hence, even against anti-sicilians, black has ways of taking control. All this sets it far apart from the other lines in 1. e4, in my estimation.

Choosing a specific sicilian was more difficult. I switched between 8 different lines before knew which I wanted to play. 
The top 4 contenders ended up being Taimanov, Accelerated Dragon, Four Knights, and Classical. 
I like all these lines. They all satisfy the criteria I listed, for the most part. They require sharpness for white to deal with properly. They're legit otherwise. They're not the most common lines, which... plays to Black's biggest advantage in the Sicilian, control and the theory burden put on White. Black has a higher winrate than white in all of these lines.

But first, why not the Najdorf? In short, it's just way too played out. And in many lines the moment you deviate you're objectively right on par with the Rauzer, so if you want to do anything other than play known theory... why even bother with the Najdorf? In practice Najdorf isn't doing very well at below masters level. It's also an enormous opening... It seems very impractical.

Anyway, comparing those 4... the Four Knights I feel is a great line for beginners. It's the line I started with. I like that it focuses on piece development early, this allows black to punish white harder when white doesn't know the theory. It's probably the easiest line to equalize with consistently for this reason. 
A reason I chose not to play the Four Knights is, if white does know the theory, the main lines are relatively forcing and predictable (both the exchange line and the sveshnikov transposition). White can play a pre-packaged response and get a good game without much effort, if he knows what to do. While this is not overly common, it gets more common the higher you climb. So while I think the Four Knights is fantastic for beginners, I don't really see it as a lifetime repertoire.

The Taimanov remedies that problem. It's more positional on account of a6, and there's not such a straightforward, easy response. It doesn't punish white as hard as the Four Knights does when white deviates, but still it's positional in a good way... white is usually left playing intuitively in a way that tilts toward equality for black. Pushing d5 and just getting a game is basically quite easy.

The main reason I decided not to play the Taimanov - which was a tough decision - was how it dealt with the anti-sicilians. Specifically the delayed alapin is stronger against the French sicilian. This limits blacks options for responding to the Alapin in general. I personally despise the Alapin, I find it very boring. It's even worse here. Black can either transpose into variations of the advanced / exchange French (extreme boredom ensues), or black can play the Barnem defense with Qxd5, where I find black is often very cramped with his queen, and again the game is quite boring. It's not just boredom, but it's the fact I'm not really challenging white in these lines either. It's just a game.

In general I feel these French sicilians play like this too. Even when they equalize it's still just kind of a game. They do equalize easy, but I want to put white to the test more and punish him when he goes wrong. 
Still, if I wanted to win as much as humanly possible at the highest level possible I probably would play the Taimanov. But that's not necessarily my goal, fun has to be a priority as well.

The Accelerated dragon is a fun line. It was a close 2nd. It's sharp, it has whole board complexity, black has a long term advantage in his pawn structure... it especially requires and rewards opening prep, which is the strongest aspect of my game. Black is scoring quite well. Even better, you can reach the Accelerated Dragon from the Reti somewhat reliably. The only problem with this line was reaching it. You either have to play the hyperaccelerated dragon, or you have to face a Rossolimo / a few other irritating anti-sicilians.

For the hyperaccelerated, I find the c3 line white can play is essentially an alapin on steroids. The alapin is the anti-sicilian I find most boring / grindy. I don't feel much has been gained over the mainline move order by playing the hyperaccelerated. Facing a stronger alapin is not something I desire to do.

But I also don't like the way 2... Nc6 deals with the Alapin, because due to the possibility of white playing a delayed alapin... your options are more limited to the standard options against the alapin - either pushing d5 / taking back with the queen, or playing the age-old Nf6 e5 Nd5 lines. Lines which are again all quite boring. Another option is to respond to the Alapin with e5 immediately, and while this is sharp and more interesting... I think whites response is fairly straightforward and often white benefits from opening the center up more than black does.

In the Rossolimo there's also not alot of room for deviating in interesting ways, it's always a grindy game. I don't feel white is forced to do alot. More importantly, black has lost control of the game. Rossolimo is a legit sicilian in its own right, white chooses to enter it and can do so against any 2... Nc6 player, including all the trendy Sveshnikov / Lowenthall players, and everyone else. So you've lost one of the biggest upsides of the Sicilian, control. Not good.

So then why classical? 
In short, it deals with anti-sicilians extremely well - possibly the best of any line. The only other contender is the Nimzowitsch sicilian. The classical is also very punishing of theoretical mistakes. It's both theoretical and focuses on piece development. 
At below-masters level I run into the anti-sicilians alot more often than I do the main lines. How a sicilian deals with the anti-sicilians is crucial factor in assessing it. In this respect there's really nothing that rivals 2... d6. The Moscow is alot weaker than the Rossolimo. The delayed alapin is terrible against d6, since after Nf6 there's no e5 push, and white cannot push d4 successfully. Dispensing with the delayed alapin also frees black up to play interesting sidelines against the move-2 alapin without worrying about learning 2 sets of complex lines for the alapin. Even better, the anti-chekhover move order is very sharp, punishing, almost never played, and avoids whites move-4 and move-5 anti-sicilians.

Compared with the Najdorf or Dragon the Classical is even better against anti-sicilians, because you can play Nc6 against the Closed Sicilian and transpose. Nc6 or e6 are the preferred moves against the Closed, since they deal with the Fiancettos and Grand Prix well. Playing d6 allows for a strong version of the Grand Prix. An early a6 is fine, but I still would say e6 and Nc6 are more testing.

Furthermore, the classical focuses on piece development and can strongly punish common, automatic white setups such as the English attack setup.

It's no exaggeration to say that the only testing line against the classical is the Richter-Rauzer. Initially this line is what caused me to give up the classical. It is extremely complex and difficult. One could argue that, since this is the only real challenge to the classical, the player can just study this line very deeply and be okay. However... that's no trivial task. While not objectively bad for black, it cuts against black very hard when mistakes are made, and the size complexity of the opening grows exponentially.

I came back and gave the line another look, and realized black has simpler, more modern ways of dealing with it invovlving an early h6, which while they may be marginally sub-optimal (a few centipawns), and so dismissed by GMs such as Sam Shankland... they are scoring extremely well in online games. Like 70% winrates for black in the most testing lines, large sample size. Whites correct moves are quite obscure. Essentially, I am settled on "cheesing" the Rauzer. It's not full-blown American cheese, just an extremely mild Swiss, but in practice it's working very well.

Given all that, I think nothing rivals the classical, especially for someone playing in an online below 2400 elo setting. Very underplayed line.

Honestly the Rauzer is objectively quite a bit better than the Yugoslav for black... people play the dragon at a high rate, however they don't play the Classical. I'm not sure why that is.

But do you get a doubled pawn structure? A lot of people don't like that.

In the f3 line (most testing line), from what I've seen thus far, there are no doubled pawns if playing the swiss cheese version.

So this is the position in question. The traditional variation was 9... b5. That variation explodes in size. A more modern line is 9... Nxd5, Forcing the queen forward... which prevents some queen rotations and bishop remaneuvers along Be3 > Bd4. Anyway... although 9... Nxd4 reduces size complexity somewhat, it's still quite complex and does lead to the doubled pawn situation. But the swiss cheese line I'm referring to is 10... h6 > 11... Bc6 here, which is relatively forcing -

And in this position white has 3 moves which really maintains an edge - 12. a3, 12 Bd3, 12. Be2. But these 3 moves, altogether, are played a total of 3% of the time at 2200+ level. Take a look at the stats -

Bd3 looks very unintuitive since it blocks the rook and strands the queen, no one plays that. Be2 looks unintuitive since you already have f3 bolstering g4. And a3... doesn't appear to do anything.

The most common moves by far are 12. g4, 12. Kb1, 12. h4, 12. Bc4. All these are common Rauzer moves. We don't get doubled pawns in these lines, since we can push d5 due to the support from Bc6, plus some odd tactics. All of them equalize or almost equalize.

12. g4 is -0.11 for black. It's already quite good. There's not going to be time for the kingside expansion since d5 is already here. 
Like 75% of people respond with 13. e5 and black gets an even larger advantage with -0.60 or so, because of this tempo on the queen / ability to trade off the bishop. If white reinforces with f4 it gets even worse for him, here's an example of the trap white has fallen into -

Hence the 69% vs. 22% winrate in this line. And this is basically the critical line, if instead of Be3 white plays Bh4, that line is also almost equal, it's +0.08, because the bishop slows down the pawn advance. I wouldn't even be afraid of the line.

Likewise with 12. Kb1 we can push d5 immediately, whites best is to take and we've pretty much equalized. Those are the two most common lines here... 
If black plays it right and plays a3 - well it's objectively almost the same as any other Rauzer.

Overall though, I think this makes managing the complexity of this line very doable, infact even good for black practically speaking, whereas the other lines with b5, or even the main Nxd5 lines... they're quite a nightmare. The problem I had wasn't the objective eval, it was the size complexity and how sharp mistakes cut against black.

Looking at f4 there look to be ways of avoiding doubled pawns there too. There are lines where you exchange queens and go down a pawn but you have good initiative and the game is like +0.2 or so, just an endgame where you can hold if you play it well. The f4 variation is considered less testing than 9. f3 anyway though, since it doesn't explode in size.

You can just study this line and play it sharply, it's +0.2 -

So I think this will all work out extremely well.

Very Cool, Indeed.

I always wanted to learn the Classical Sicilian, but I never did.

I sort of always found myself preoccupied with other lines.

My only experience with Classical Sicilian is from White side.

When I use to play the Open Sicilian, I did some research on a line.

My Chess Theory + Line was very slim.

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Keep in mind, I wasn’t high rated when I studied this line from White side.

My Opening Preparation was only 7 moves deep which is pretty sad.

It’s kind of embarrassing to even imagine I had Opening Preparations so weak, but yeah I was low rated. I think I was like 1,500.

Obviously, I play the Closed Sicilian.

I have played the Closed Sicilian for many years, now.

I haven’t relearned or redone any of my Opening preparation in the Open Sicilian vs. Classical Line. I wrote my lines and where ever I stopped is where I stopped at the time.

The 6.Bc4 line is solid line vs. Classical.

The preparation I did at the time was light, but it seemed okay.

Have you encountered any 6.Bc4 players or do you face many 6.Bg5 players?

@Compadre_J I'd say it's about an equal distribution of Bc4 and Bg5. Maybe slightly more Bg5. 
Bc4 isn't bad, it's whites 2nd best response probably, but it's just not the Rauzer and black is doing fine. I play the Anti-Soziin which is Qc6 in response. There are a few specific line in the Sozin that can be quite sharp, but it's nothing insurmountable, just a typical sicilian type position and just requires good prep to deal with. Most of the lines black gets a good position.