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15 votes
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What should be the value change if pawns are doubled?

Start with whatever and tune it. That's how chess engine programming works - you start with some number, and then tune it. For example you start with -5, then create another version with -10. You get ...
Allure's user avatar
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15 votes
Accepted

Was this “caterpillar” strategy a good way to advance my pawns?

tl;dr: "Yes." Discussion: Technically, this position is governed by the basic concept of the "Outside Passed Pawn" and the winning method is to use that pawn to restrict the opposing king's ability ...
Arlen's user avatar
  • 5,264
14 votes

In Bb5 systems against the Sicilian, why does White exchange their b5 bishop without playing a6?

Some things that are probably part of the answer, but probably not complete and concrete enough: 1...a6 won't come. There is no threat to a pawn on e5, the knight isn't pinned, the only point of 3....
RemcoGerlich's user avatar
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14 votes
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Why is e5 the strongest move here for white?

You've given some good, very long-term reasons not to play e5. But in this position, dynamic considerations outweigh these long-term reasons. Look again at the position: you have developed (if you ...
Allure's user avatar
  • 27.9k
11 votes

Was this “caterpillar” strategy a good way to advance my pawns?

Overall, that is totally fine, and it worked great. That said, without a detailed calculation of any promotion and stalemate possibilities on the k-side, the easiest win will be running to b2 and just ...
PhishMaster's user avatar
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9 votes
Accepted

Capture towards the center vs. undoubling

In this particular position both ...ab6 and ...cb6 are reasonable. Generally speaking I would prefer to take toward the center because the doubled pawns are not weak at all when they have neighbours ...
Evargalo's user avatar
  • 16.4k
9 votes

Was this “caterpillar” strategy a good way to advance my pawns?

White is in zugzwang so the basic idea of forcing white back using the pawns for extra tempos is perfectly correct. You still need to figure out how to queen without stalemating but you have the ...
Savage47's user avatar
  • 4,269
7 votes

What should be the value change if pawns are doubled?

There's no real rule for how much do doubled pawns (or any other kind of weakness on the pawn structure) worse your position. There's not even a rule for piece value, specially if you'll add bonuses ...
David's user avatar
  • 16.3k
7 votes

In Bb5 systems against the Sicilian, why does White exchange their b5 bishop without playing a6?

A few things: 1) White's actually not wasting any tempi. He has to move his bishop out anyway (in order to castle). Then, once on b5, taking on c6 doesn't waste a tempo since Black has to spend a ...
Inertial Ignorance's user avatar
6 votes
Accepted

Are connected doubled (4 pawns on 2 files) a weak structure?

It is a solid structure indeed, avoiding one of the most important weaknesses of doubled pawns, which is that they're generally hard to protect. Also, they're less easy to block than just a c- and d-...
Glorfindel's user avatar
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6 votes

Was this “caterpillar” strategy a good way to advance my pawns?

It was OK, but unnecessary. You could have left your "back" pawn on the starting square to make your opponent lose more time while going to capture it. Then you are free to go into the queenside to ...
David's user avatar
  • 16.3k
5 votes

What should be the value change if pawns are doubled?

Doubled pawns aren't necessarily bad. They typically mean an open file and often can improve control of the center. There's really no way to answer unless I know how you value the mobility of the ...
Savage47's user avatar
  • 4,269
5 votes

Are connected doubled (4 pawns on 2 files) a weak structure?

The structure itself isn't weak, since as you mentioned all of the pawns are solid and protecting each other. The problem is that you can't do much offensively with these pawns. Take the following ...
Inertial Ignorance's user avatar
4 votes

In Bb5 systems against the Sicilian, why does White exchange their b5 bishop without playing a6?

The main reason is that White does not want to face Nd4in many lines. They want to make sure they will "hurt" Black's pawn structure with Bxc6. Compare this line with others where the Black knight is ...
David's user avatar
  • 16.3k
4 votes

In Bb5 systems against the Sicilian, why does White exchange their b5 bishop without playing a6?

A lot of it is simply to create an imbalance. Nakamura has mentioned this before about a different opening B-for-N trade, and sometimes it is done without even getting doubled pawns in return, like an ...
PhishMaster's user avatar
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3 votes
Accepted

Structure-better structure or bishop pair in the endgame?

More often than not, the Bishop pair will compensate for doubled pawns in an endgame. Your unopposed bishop would have to be pretty bad (and therefore your overall position) if it's influence did not ...
Ywapom's user avatar
  • 6,111
3 votes

Why is e5 the strongest move here for white?

I think the (already good) answer left out a very concrete important point. White has a scary lead in development. Standard plan: rip open a few lines and massacre the king who is a sitting duck in ...
Hauke Reddmann's user avatar
3 votes

When to (and when not to) play Bxc6 (i.e. BxN) as White in Ruy Lopez?

It is just a matter of taste. There are pluses and minuses to the move, but the strategic idea is gaining a better pawn structure. I have played the Exchange 4.Bxc6; the Deferred Exchange 4.Ba4 Nf6 5....
Ywapom's user avatar
  • 6,111
3 votes

What are the reasons why I should not try to take a Knight with my Bishop if it'll result in doubled pawns?

There are a few disadvantages: You trade your light-squared bishop, your best attacking piece. You give Black the bishop pair. The likely followup is an exchange of queens and an early endgame. If ...
Tom Au's user avatar
  • 12.4k
2 votes

Are connected doubled (4 pawns on 2 files) a weak structure?

The structure lacks mobility and is therefore inherently weak. The c2 and d2 pawns can not advance if attacked.
Ywapom's user avatar
  • 6,111
2 votes

Beginners question: The double pawn

Excellent discussion of doubled pawns by Gserper on chess.com Nov 2012. Botvinnik was first World-class player who liked doubled pawns. Kasparov noted Botvinnik loved to grab the center and was not ...
dlemper's user avatar
  • 791
2 votes

Beginners question: The double pawn

There are two important things to note about doubled pawns. 1: They are good at defense. 2: They are bad at moving forward. [fen "8/5p2/6p1/ppp5/5PP1/1P4P1/1P6/8 w - - 0 1"] In this diagram from ...
David Miedema's user avatar
2 votes

What are the reasons why I should not try to take a Knight with my Bishop if it'll result in doubled pawns?

Let's see, what is the original question? The poster thinks that taking a knight with a bishop should be good if it results in the opponent getting doubled pawns. And the poster also specifically asks ...
Dennis's user avatar
  • 121
2 votes

Capture towards the center vs. undoubling

Here all is about whether white a-pawn will be strong passed pawn or weakness on semi open file. Possible undoubling is just a side effect of more important consideration. If you can blow the kingside,...
hoacin's user avatar
  • 3,286
1 vote

What should be the value change if pawns are doubled?

it depends they may be worth more if they open a file for a rook in a somewhat closed position
foo yuk's user avatar
1 vote

Structure-better structure or bishop pair in the endgame?

It depends on the position, but a bishop is generally considered strong of play is on both sides of the boards and it's an open board. I would think that a sample position would help to understand ...
SubhanKhan's user avatar
  • 2,158
1 vote

Was this “caterpillar” strategy a good way to advance my pawns?

From the end position without the queenside pawns White can move to g1, claim the opposition, and have a draw. If you had just advanced the front g pawn until it got to g3 you would have g6 available ...
Ross Millikan's user avatar
1 vote

Was this “caterpillar” strategy a good way to advance my pawns?

It was a very sensible strategy. You never have to worry about stalemate because at the key moment, like round about now, your king can head over to the queenside to take the pawns on b2 and a3 and ...
Brian Towers's user avatar
  • 98.4k
1 vote
Accepted

When to (and when not to) play Bxc6 (i.e. BxN) as White in Ruy Lopez?

4 Bxc6 became popular after Fischer made extensive use of it. He followed up with 5.O-O and although this is no longer fashionable at GM level, a lot of lesser players are uncomfortable. White can ...
Philip Roe's user avatar
  • 8,633

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