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I'm a casual, semi-serious chess player and have been an active player for over 10 years. In my time playing, one of the most unusual openings I have had the pleasure of playing against is known as Alekhine's Defense:

[FEN ""]

1.e4 Nf6 2.e5 Nd5 3.d4

In the above line I gave the usual move 3.d4. This seems like a very good position for white, and an underdeveloped position for black. I am, however, more interested in the less common variation 3. c4:

[FEN ""]

1.e4 Nf6 2.e5 Nd5 3.c4 Nb6

which is my usual line of play. From my perspective, the aggressive 3.c4 seems like a better move, buying a pawn development move with a tempo (the pawn at c4 is defended by the white bishop after the response 4...Nb6.) In fact, there are over 300 tournament games along this line of play, indicating better chances for white in the final position above.

I have read in chess literature that if an attacking player is not careful with Alekhine's Defense, he may easily overextend his pawn structure, one of the subtleties of this particular openings. I'd like to know if the last variation I described above is already considered an overextended pawn structure, if so why, and if not, what must white be wary of in order to avoid overextending.

Furthermore, what does black hope to accomplish by placing his knight in peril so many times? Does the fact that white must overextend himself slightly in order to chase the knight multiple times outweigh the opportunity cost of moving the same knight 4 times in the first 4 moves?

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Note that a lot of the time that White plays 3.d4 he will end up playing c4 anyway, and pretty much every time he plays 3.c4 he will follow up with d4 (usually on the next move). So the main difference is that 3.d4 is more flexible and doesn't commit you to c4 yet. –  dfan Mar 12 '13 at 16:56
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4 Answers

In short, white may well be overextending.

From black's point of view¹, white is offering many targets for black to attack :

  • d4 as c3 is not possible anymore, and if e5 is traded for d6.

  • e5 if d6 gets traded for d4

  • c4 if white's king bishop moves anywhere useful

  • Behind the pawns is a lovely place to land knights (d3 via b4 is not uncommon, e3 via f5 seldom happens…)

Once white's pawns are fixed, one can wonder about what advancing them actually achieved : white loses as much time pushing pawns as black moving the knight.

¹ which I adopt as an all-time Alekhine defense player myself.

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Does the fact that white must overextend himself slightly in order to chase the knight multiple times outweigh the opportunity cost of moving the same knight piece 4 times in the first 4 moves?

Consider that white has made four pawn moves, including moving one of them twice. Further, black has a piece off the back row and white does not. Is that really any better?

Furthermore, what does black hope to accomplish by placing his knight in peril so many times?

As you said, the idea is to encourage white to over-extend. That's the whole point of Alekhine's Defense. Note that that black's knight is doing fine. There's no real peril to the peril!

there are over 300 tournament games along this line of play, indicating better chances for white in the final position:

Well, that's when grandmasters play. You're probably not a GM and won't be playing GMs. Amateurs waste tempi all the time and make imperfect moves most of the time. The question for me is, "which player has to excel in order to win the game?" And what I mean is, it's possible to have game positions where white can win if he plays like a monster, but black can win if he's average.

For this case, white has more space and has moved no pieces. Black has full flexibility and has a piece out, and not on too bad a spot. It's game on!

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Your position is potentially overextended. Because you have moved the c pawn all the way to c4, it can no longer be put on c3 to create a pawn chain with d4 and e5. This, your d pawn is "weak" because of the move.

Experience has shown that Black incurs a greater disadvantage (multiple moves with the same knight), than White. If this is the "only" weakness White creates, you're fine.

The problem comes with potential followup moves. For instance, if you are tempted to play the pawn to c5 to chase the knight, you might end up creating a "hole" on d5 for Black.

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Go see how Houdini crushed Rybka with Alekhine's defense. I think it's a solid proof for the weaknesses provoked by black.

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Hi Goodriddance, do you have a link to the game or the actual moves? Welcome to the site! –  Andrew Apr 4 '13 at 17:00
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To expand on Andrew's comment, Stack Exchange websites are intended to be useful repositories of questions and answers. You could make your answer much more useful by editing in a link to the games you mention, some additional commentary on the strategy, or even providing the PGN for such a game. –  Jonathan Garber Apr 4 '13 at 20:26
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