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How do you decide which way to castle?

It seems castling kingside can be dangerous because of white's extra kingside space he often gets in the French Defense. Also most of my pieces are naturally on the queenside making it difficult if they're needed for defense on the kingside. I'm curious about if castling queenside is good or not, since you use your pawns to expand on the queenside its feels like a lack of a pawn cover for your king?

Sometimes I end up not castling at all in the French because of this. I understand that the answer is rather situational but can someone explain the theory on this?

6

If you can block the pawn structure on the queenside then you can consider castling queenside, for example in this line

  [StartPly "12"]
  [White "White"]
  [Black "Black"]
  [FEN ""]

  1. e4 e6 2. d4 d5 3. e5 c5 4. c3 Nc6 5. Nf3 Qb6 6. a3 c4

Also, in the Winawer poisoned pawn, black often castles queenside in the middlegame because kingside castling is not possible and to bring the a8 rook into play, e.g.

  [StartPly "32"]
  [White "White"]
  [Black "Black"]
  [FEN ""]

  1. e4 e6 2. d4 d5 3. Nc3 Bb4 4. e5 c5 5. a3 Bxc3 6. bxc3 Ne7 7. Qg4        Qc7 8. Qxg7 Rg8 9. Qxh7 cxd4 10. Ne2 Nbc6 11. f4 Bd7 12. Qd3 dxc3 13. Nxc3 a6 14. Rb1 Na5 15. h4 Nf5 16. Rh3 O-O-O  

Otherwise you generally castle kingside. Sometimes Kf8 is played to defend a pawn on g7, e.g. after Qg4, but that depends on the specifics.

1
  • The reason for castling kingside instead of not at all is the rook on h8 gets to play in the game after ...f6. Otherwise you can leave the king in the centre but without a way for the rook to play (...h5?) you're playing a rook down.
    – magd
    Apr 11 '16 at 7:26
3

I have trouble telling what's theory and what's my practical notes, but one thing immediately comes to mind.

Castling queenside can be nice in the Winawer, but it may be almost necessary in the MacCutcheon variation:

  [White "White"]
  [Black "Black"]
  [FEN ""]

  1. e4 e6 2. d4 d5 3. Nc3 Nf6 4. Bg5 Bb4 5. e5 h6 6. Bd2 Bxc3 7. bxc3 Ne4 8. Qg4 g6 9. Bd3 Nxd2 10. Kxd2

You can see h4-h5 and Bxg6 are constant threats. Rh3 targets a rook lift, f6 is a hole for the queen or knight, and so forth.

Black can even play ...c4 (as in the Advance variation above) and target the weak a- or c2- pawns. White's pawns point towards the kingside, and an a5 push is hard without an exchange sacrifice. In this case, advancing pawns on the queenside makes it safer, since it locks the white c-pawns and shuts out the light-squared bishop.

If the c-file is up for grabs, the black king may be able to duck to b8 after castling and make it easier to trade off rooks. It's hard to open the a- and b- files, though a possible c5 or d6 outpost may be a nuisance. If the black king were on g8 after kingside castling, it would have ground to make up to get to the c-file or, in general, participate in the endgame. Your point about black's queenside pawns potentially moving and making weaknesses is a good one--you probably don't want to castle that way if you've moved them, the exception being a MacCutcheon-ish b6/Bb7/Nc6 formation, or where you've played ...a5 and White's played a4, and you control b4. Again, you want to make sure a knight can't slip into d6 or possibly c5.

But if pieces are traded off, or White's bishop on h3 is dangerous, ...Kd7 (hiding behind a wall of pawns) may also be quite good.

I think one side note is that, while castling queenside can be good, the central pawn bunker affords Black the option of delaying castling at times if there are other useful moves to make. This may not be theory, but it often happens if white blunders the d4-pawn in the opening. The e5 pawn can provide a kingside attack that is hard to defend in practical play. Black may want to push White's pieces away from d4 and castle to the wing White avoids.

Castling queenside may also be desirable in the Burn variation (...dxe4 instead of ...Bb4) since after Nxe4 Be7 Bxf6 gxf6 Black gets a hold on e5. There, castling kingside lets White castle queenside and have an attack with ready-made targets. Black should use the half-open g-file for some prospects, but staying in the center isn't an option as d5! may hurt.

If White has pointed pieces at the kingside and Black hasn't made a lot of queenside holes, queenside castling may be very strong indeed. It can, however, be vulnerable to a timely Ng5, threatening the f-pawn, if Black has not found the time to play ...f6.

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