Best move order for Classical Sicilian

When you are playing the Classical sicilian (B56-69) you can either go through the old (2...Nc6) or the modern (2...d6) move order. There are several ways for white to deviate from the main lines in either of this move orders. Which do you think is best? Which do you think is white's best chance to deviate?

Bb5 in both cases? That's what I go for

Sorry, I expressed myself badly, Which do you think is Black's best move order when you take into account white's possible deviation?

Oh ok, my bad, can't help you on that I don't play the sicilian.

It depends on which Anti-Sicilians you'd rather deal with.  When I used to play the Sicilian, I played the Taimanov, which also has multiple options on how to arrive there (2...Nc6 or 2...e6).  I played 2...e6 to avoid the Rossolimo.

Quite frankly, just about every Anti-Sicilian except the Rossolimo (Yes, including the Moscow) are all a complete joke.  The reason I quit playing the Sicilian myself is because of the Open Sicilian (3.d4, White's best move!).

In your case, where your choices are 2...Nc6 vs 2...d6, here's what you must consider:

Rossolimo or Moscow?

Transpose to 2...d5 Alapin or Unique Sideline completely different from the Alapin after 3.c3?

Don't allow 4.Qxd4 or Allow 4.Qxd4

Don't allow the Prins (3.d4, 4.Nxd4, and 5.f3) or allow the Prins.

You can't pick and choose in each list.  You must either accept ALL the ones to the LEFT of the "or", or else accept ALL the ones to the RIGHT of the "or".  If you want to deal with the ones on the left, play 2...Nc6.  If you want to deal with all the ones on the right, play 2...d6.

Thank you for the detailed answer.

2...Nc6 seems to be a better move order for me because it cuts out more tries than 2...d6 but it allows the Rossolimo.

Is the rossolimo such a different beast when compared to the moscow?

Yes!  Saying the Rossolimo is different from the Moscow is like saying the Nimzo-Indian is different from the Bogo-Indian.  One involves trading Bishop for Knight for structural damage, the other entails a trade of Bishops with structure intact.

"Quite frankly, just about every Anti-Sicilian except the Rossolimo (Yes, including the Moscow) are all a complete joke."

I do see GM's play anti-Sicilians though.  They occasionally deviate from 3. d4.

Just because a GM plays a line does not make it good.

A) Is it a rapid game?

B) Who are they facing?  Playing someone weaker they will play dead equal openings figuring the 2200 player won't survive a non-theoretical position all the way through rather than dealing with a theoretical battle in the lower player's wheel house, like the dragon.

C) Is White looking for a draw rather than a win (i.e. already ahead in a match)?

You have got to do better than that!  You do not see these lines played at the top GM level in high pressure situations to win except maybe the extreme occasional use for surprise value.  Otherwise, it is typically Open or Rossolimo against the Sicilian.

Reasonable questions.  

Well, if I ever come across a 2600+ GM playing an Anti-Sicilian in the next several years in a Classical OTB rated game I will post it here on this thread.

Last February I learned the silician defence.

My opinion: Rossolimo - more complex game with many reasonable choices for black so the better player has a good chance to grind down the other and Moscow - more likely to quickly [after d5] wind down into a boring draw. [The only line of Rossolimo I'd be concerned about has never been player against me.] Morra - unsound and easy to play against if you know a few ideas [like Qb8 rather than Qc7]. Alapin - black only gets in trouble when he/she tries for more than a slight  plus in opening.  closed - there are at least 2 black formations that are rick solid against it. Grand Prix - here you need to know a few critical moves; you have slight + if you do and get checkmated if you dont. Wing gambit - hahaha. White can also play a number of waiting moves that turn out to be often useful later and can make black try for more than = and over step.    .... I think that's all I've seen.  Bill (ps-I generally play 2. ... Nc6)

I have a question for you and sorry if this is off subject, but what variation of the Taimanov were white players playing to cause you so many problems?

I haven't exactly excelled at the black side of this opening, but that is mostly due to my mishandling of the middle game positions; which are not exactly intuitive for me. However, you're most definitely facing a little better competition than me.

In analysis, I don't see where white can cause any problems against the Najdorf or Taimanov ...

The Sveshnikov seems pretty solid, too, but of course black is equalizing - not statistically, but "theoretically" (for whatever that's worth) - in almost every line of the Sicilian or anti-Sicilian; it's just a matter of how deep you get into the lines prior to equalization. With some defenses, black equalizes more quickly, and others require almost 20 moves of memorization.

Absolutely any opening I've analyzed both with an engine and with an opening explorer style statistical database of human vs human games, simultaneously, black is equalizing according to the engine, and white is getting the better of it in human vs human stats.

This is obviously a critical point most amateurs miss while developing an opening repertoire. A human doesn't have the defensive capabilities of an engine. Scientifically, if 95% of white's moves are playable and 95% of black's moves are losing, the engine will call it equal as long as there is that 1 move available that is equal. In human vs human play, white is going to destroy black.

Just wondering...What line with black makes you say that the Moscow is a joke? @ThrillerFan

Black is equalizing too quickly … Just go look at opening explorer. Even in human vs human play, black is as good or better before even 10 moves into the game.

Sure some body will claim it's "playable" and fine and blah blah blah blah blah

We're not a bunch of GMs that know every subtly of main line opening theory, having a memorization contest, just trying to get each other out of theory, etc..

An amateur is better off learning main line opening theory and why it's scientifically better.

In the context of chess as a whole, maybe the Moscow is indeed a joke or maybe my buddy is being a little harsh. I don't care, but it is "sub-optimal."

According to opening explorer in chessgames.com, white is winning only 29.9% and black 29.4% with draws counting as 40.7% … and that's as soon as the bishop lands on b4 on only the 4th move ...

If black responds with 4 … Nd7, then black is winning 35.1% to 28.7% ...

Yeah, that is a big joke ...

Regardless of how white responds, white can't do any better than get even. Black is winning the majority of the games.

Keep in mind, this isn't scientific, but just how people have faired against other people.

I'll take black's chances, though.

Anti-Sicilians are dumpster scum.

Dude he never said that the Moscow was a joke

He said any anti-Sicilian except Rossolimo and Moscow is a joke

Also @ThrillerFan

I don't think you should be making a claim like that (unless you're like a GM or something). What about the Alapin? Grand Prix Attack? Closed Sicilian? Chekhover? Prins?

After you go work on your reading skills, then we can discuss chess.

Who