Sicilian Rossolimo

I have been playing the Rossolimo, 3.Bb5 against 2...Nc6 in the Sicilian. I generally get a decent game with it because it's obviously sound, developing the kingside with O-O to follow. But although I've read it up in opening books, most recently the analysis in Christof Sielecki's Keep it Simple: 1.e4, I have to say I don't really understand what my plan should be. I find the lines hard to memorize for this reason: sometimes White takes the knight, sometimes retreats the bishop; sometimes pushes the e-pawn, sometimes not; sometimes plays d3, sometimes d4; sometimes goes for a Maroczy bind with c4, sometimes supports the centre with c3). It's all very well to be flexible, but there are few tactical motifs to remember and the positional aims just seem very mixed up. Can anyone give me a few rules of thumb, please?

As one that does not play the Rossolimo from either side (White - Closed Sicilian, Black - French Defense), I cannot say a whole lot about rules in the Rossolimo, but once you said the word "memorize", I can already say that you are taking the wrong approach.  Openings need to be understood, not memorized.  You need to understand the ideas.  If you understand the ideas, the moves will come naturally.  It should not be done the other way around, which is a common mistake.  They try to memorize the moves and then guess the ideas.  Wrong way to do it!  You need to understand the ideas first and then the moves will come naturally.

For example, after 1.e4 e6 2.d4 d5 3.Nd2 c5 4.exd5 exd5 5.Ngf3 Nc6 6.Bb5 Qe7+ 7.Be2 Qc7 (why?  So that if 8.dxc5, Black can recapture with the Bishop instead of throwing the Queen out in the open early on) 8.O-O Nf6 (Now we see another idea, Black wanted to develop his knight to the active f6 square rather than e7, which he has to do in the 6...Bd6 line) 9.Re1 (A prophylactic move).

Now, there is no need to have memorized the line.  What does Black want to do?  Castle and not be passive.  Well, 9...cxd4 as there are no good discoveries for White.  Now, after 10.Nb3, working to recover the pawn, 10...Bb4!, attacking the Rook and if c3, Black gets a pawn with no good discoveries.  So 11.Bd2 and now 11...Bxd2, still attacking the Rook and getting rid of his hanging Bishop.  White must take back and Black can safely castle.

Understanding all of this, and understanding the fact that 10.Bd3+ or 10.Bb5+ are useless, we figure out a way to avoid the passive 9...Be7 and now on move 12, Black will castle.

If you cannot describe in words what you are doing, and all you can do is reel off a list of moves, you clearly do not understand the opening!

That's not the point.  I'm an experienced player (even if not a high-level one) and am not planning on doing any rote learning- if I was, the moves given by Sielecki and others would do for that. My problem is precisely that I don't understand the ideas behind this particular opening, and am asking for help with that. Lessons in the French are no use to me in that respect.

The point was not a lesson in the French.  It is a lesson on the approach to studying any opening.  I used the French as an example because that is what I know.  The point to be made is not a lesson on the French.  It is a lesson on how to study.  You are asking how to get the ideas in that opening.  I illustrated the mentality approach to take.  You now need to take that approach and apply it to the book you are reading.

It is just like Algebra.  If you are having trouble with say, matrices to solve 3 equations with 3 unknowns, then you go to the teacher to learn the right approach to solving your problems.  You do not hand her the problems and say "here, do these problems".  It is the same thing here, I am giving you the general approach to learning an opening.  I have taken this approach for many openings.  Some stick, like the French, and I continue to play it.  Others do not, like the Grunfeld, and I throw it away and play something else.  You need to take this approach with the Rossolimo and determine if it is a keep or a dump!

You give a generic question, you get a generic answer.  If you are looking for people to spell out every idea in said opening, that is what you hire and pay a coach for.  If you had a very specific question that required a specific answer, you'd likely get the answer from a Rossolimo advocate, but nobody is going to write you a full 50-page novel on the entirety of the Rossolimo.

Therefore, If you are going thru the book on the Rossolimo, and cannot answer the question "Why did White play this?" Or "What are White's general plans?" Or "What threats must I watch out for and where are my weaknesses?" (Keep in mind, a weakness does not have to be a pawn or piece, it could be a very weak square, like e5 in the Stonewall Dutch), then maybe it is not the line for you!

If you cannot answer those Questions, then go for a different line.  Nothing says you have to take the cookie cutter approach of following every line in a single repertoire book.  As long as you account for possible transpositions, you can mix and match.  Maybe you understand his approach against the Caro-Kann and 1...e5, but just don't get what he describes against the Sicilian or French, and maybe you have to look for other resources.  Maybe the Closed or Alapin or Open Sicilian is something you'd understand better, and maybe you get a better grasp with the Advamce rather than the Exchange French.

If you want more specific than this, you need to be more specific in your questions.  Like maybe if you don't understand why White played some weird move on move 14, and want to know why that variation is better than some other sideline on move 14.  But a generic question on an entire opening gets a generic answer.

You may have missed the specifics in my question (not surprising, since you don't play the opening). They are these:

1. Bxc6 or retreat the bishop.

2. e5 or leave the pawn where it is.

3. d4 or d3.

4. c3 or c4.

In none of these questions does it help to look at grandmaster games, as grandmasters play all of them. And so do I, reacting to the position according to what seems good at the time. But it would help a lot if I had a rational basis for making those decisions instead of having to think it out from scratch each time. Openings have learnable principles which can help in such decisions (eg, it's a good idea for Black to try to undermine the White centre in the French by moves like c5 and f6, and for White to be prepared to deal with that). They also have known traps and tactical motifs (eg Black needs to be aware of the Greek Gift sac). Despite having read up a fair amount on the Rossolimo, I don't have a strong idea of either, largely because it is such a flexible opening, allowing for many possible plans. That's why I'd appreciate the advice of a Rossolimo practitioner to help me choose between them.

And the answer is not the same all the time.

After 1.e4 c5 2.Nf3 Nc6 3.Bb5, the ideas after 3...g6, 3...e6, 3...d6, 3...Qc7?!, and 3...Na5?! are completely different!

So again, you've got to be more specific.  To expect a straight answer of "always play 4.Bxc6 would be like saying 2.Bc4 is good no matter what Black plays.  Against 1...e5, It is fine because the a2-g8 diagonal is weakened for Black by the move 1...e5.   Against 1...e6 or 1...c6, the move 2.Bc4 is total crap.

Same with the Rossolimo.  What is good in one line is garbage in another line.  So your questions are still too generic.

Some lines e5 is good.  Others it is merely weak and the pawn will drop 10 moves later with no compensation for it.

So which line are you talking?  3...g6?  3...e6?

The one that I can tell you is that c4 is rarely good in the rossolimo, and more frequently played in the Moscow (2...d6 3.Bb5+)

Positional openings are just like that.

In the Rossolimo, both sides have some freedom regarding how to develop their pieces. You are supposed to figure out the 'holes' in your opponent's camp and poke at them. Different setups have different 'holes' and logically require different strategies from the other side.

It's quite different from openings like, say, the Advanced French, where pawns are fixed in the center and play always revolves around a few general themes. The Rossolimo is a collection of many pawn structures, each with distinct positional themes.

I don't think the Rossolimo is suitable for players below ~1800 FIDE (or ~2000 chess.com blitz). But if you do like that opening, you might want to divide your materials by pawn structure and study each structure individually.

Excellent answer - precisely what I have been trying but unable to get across.  And another reason I used the French example as a comparison.

Like you say about the French Advance, the options are limited.  Expand the Queenside with a3-b4 (usually best attempt against Qb6 lines) or castle and attack the kingside (best against slower systems).

There are other openings with limited paths that can be taken.  They do not have to be closed to have limited options.  They could be wide open.  The key is the limited number of fluid pawns.  They may be blocked, or traded away, and so wide open positions also have limited (though not just one) options.  The Petrosian Kings Indian (7.d5 instead of 7.O-O), The Czech Benoni, the Petroff, the Berlin, the Danish Gambit, along with lines like the French Advance already mentioned, fit this category.

But then you have openings that are just the opposite of that where due to the fluidity of the pawns, you have to learn the general concepts at a deeper point in the opening, because due to the fluidity of the pawns for 1 side or both sides, each sub-variation must be treated completely differently!  These would include openings like:

The Nimzo-Indian

The Caro-Kann Fantasy Variation

The Grunfeld

Larsen's Opening (which can actually lead to a Nimzo-Indian in reverse)

Rossolimo Sicilian

Alekhine's Defense

Trompowsky Attack

There are others too, but these stand out.  With yours in that list, and this post along with the previous one, do you see now why I say that your post is not specific enough to give a straight answer and only a general response can be given, and that it would be like writing a 50 page novel to answer your question the way you word it?  It is not like I am trying to be a wise guy or snotty about it.  It is simply a fact that it is too broad of an opening to have general principles at move 3.

If you want to get a better feel for the opening, I think you should just practice with it (in blitz games). And analyse the opening phase of your game afterwards. I don't think it's a bad idea to look at the theory to get a rough idea at how to respond to certain lines, but memorizing should generally be used if you intend to prepare for a specific opponent.

I just wrote a blog article about how you can approach Rossolimo structures: https://www.chess.com/blog/SharpCube/a-simply-guide-to-understand-the-rossolimo
Hope this helps

Thanks, very helpful.