During the Pro Chess League season this year (which still has not ended, by the way — the finals have been postponed until September) Robert Hess made a comment that jolted me awake. “When I’m evaluating a position,” he said, “The first thing I look at is who has the pawn breaks?”

What?! The first thing I look at is who is ahead in material. Pawn breaks may come fifth or sixth, or maybe even lower than that, on my personal list. But Robert Hess is a grandmaster. I am not. Ergo, it would behoove me to listen to him.

Hess’s point is that the player who has more playable pawn breaks has more control over the evolution of the position. It’s a tremendous advantage to have. Imagine that you’re in a race and you have the right to change the course, say by opening up a shortcut. You could even be behind, but if you have the shortcut advantage you can catch up.

The definition of a “playable” pawn break can be quite loose, and this is one of the subtleties in the concept. Often pawn breaks may look unplayable — they cost you a pawn — but they change the position in important ways, opening a line for your pieces or closing lines for your opponent’s pieces. Or they may weaken your opponent’s pawn structure and create targets for you to attack.

Recently I lost a game against my computer in which I missed not just one but four pawn breaks that would have given me excellent attacking chances. Ironically, the one time I did play a pawn break was the wrong time, and it didn’t do very much to improve my position.

This is another humiliating game for me because I lost a very superior position. But I’m showing this game not to humiliate myself, but to show you how to improve your game. (For the record, I do think I would have played some of these pawn breaks in a tournament game. But the fact that I could not find them when playing a blitz game means that they are not the first thing I think about, as Robert Hess says they should be.)

Fritz 17 — Dana, 40 moves in 10 minutes

Position after 18. Bd2. Black to move.

FEN: 1r3rk1/pp2n1p1/2pb1nq1/3p1p1p/3Pp2P/2NPPP1R/PPQBN1P1/R4K2 b – – 0 18

As usual Fritz played a super funky opening, which I’ll skip, and we will start on move 18. Who has the advantage in the above position? Let’s think about the position Robert Hess style. Who has the pawn breaks?

Well, White has essentially zero pawn breaks. The move g4 is never playable because it opens lines that Black can use to attack the White king. Over the very long term White has two possible breaks with b2-b4-b5 and a2-a4-a5-a6, but these take a long time to carry out and are not exactly terrifying.

How about Black? Well, he has a pawn break with … c6-c5 that may be good at some point but isn’t good yet. And he has a break with … f5-f4 that is like a hand grenade. You’d better pick the right time to pull the pin, but it can do a heck of a lot of damage. So Black has two pawn breaks, and one of them is kind of meh but the other should be checked carefully on every single move.

What if we play it now? Here’s where beginner chess is a lot different from master chess. The beginner looks at 18. … f4 and says, “You can’t play that, because it’s attacked 3 times and only defended once.” But the master says, “Please! Go ahead and take it!” And after the beginner plays 19. ef (or Nxf4 Bxf4 ef), Black plays 19. … ed, forking White’s king and bishop. Here we see the idea of a sweeper; the move 18. … f4 swept open the a2-h7 diagonal and increased the pressure on White’s d3 pawn.

Then the beginner says, “Okay, you got me there, but you still can’t play 18. … f4 because the e-pawn is attacked 4 times and only defended 3 times. So I’ll play 19. de instead.” The master says, “Make my day!” and plays 19. … fe 20. Bxe3 Nxe4. Not only has Black swept open the a2-h7 diagonal, he has also swept open the f-file. So the knight cannot be taken by the f3 pawn, and meanwhile it threatens 21. … Ng3+, with a discovered attack on White’s queen. If White tries to break the pin with 21. Kg1, now Black has 21. … Ng5! 22. Qxg6 Nxh3+! So 21. Nxe4 looks forced, and after 21. … de 22. Kg1 Black can obliterate White’s kingside with 22. … Rxf3.

Moral: When determining whether a break is “playable,” don’t just count the attackers and defenders. Look at all the ways in which the move changes the position.

Instead, I played the less accurate

18. … de 19. Qxd3 Ne4

It’s interesting how I have the right themes in mind, but they aren’t as effective in this move order. The move Ne4 was much more forceful in the previous line, where it took a pawn and threatened a discoverd attack on White’s queen.

20. Qc2? …

This gives me another shot at our favorite pawn break…

20. … Nxd2?

Which I whiff on again! Once again, 20. … f4! blasts open lines, and all the tactics favor Black. If 21. fe fe+ wins back the piece and opens up lines against White’s king. If 21. ef Ng3+ wins the queen with a discovered check (one reason that 20. Qc2 wasn’t so good).

21. Qxd2 f4?!

Ironically, when I finally played the pawn break it was no longer a clear winner. My thinking was that after 22. Nxf4 Bxf4 23. ef Nf5 my knight is taking aim at a lot of weak points in White’s position: h4, g3, e3, d4. But nothing really clear comes out of it after, say, 24. Re1 Qf6 25. Re5 Nd6 (threatening Nc4) 26. Rxh5 Qxf4 27. Qxf4 Rxf4. It feels as if Black has given away his advantage.

However, Fritz decided not to accept the pawn and instead played

22. e4 de 23. fe …

What do you think we should do here? All together now…

Position after 23. fe. Black to move.

FEN: 1r3rk1/pp2n1p1/2pb2q1/7p/3PPp1P/2N4R/PP1QN1P1/R4K2 b – – 0 23

PAWN BREAK!! Now is a great time for 23. … f3!, forcing open the f- and g-files, which are exactly the files that White does not want to have opened. If 23. … f3 24. Rxf3 (or gf) Qg4 Black will win back the pawn for sure and probably more with the idea of … Ng6, …. Nxh4, etc.

Instead my attention was focused on the wrong part of the board. I saw White’s pawn duo on d4 and e4 and thought that I wanted to reposition my bishop to I could put more pressure on them. So I played

23. … Bc7,

not a horrendous move but still a missed opportunity. Fritz answered

24. Qd3 Rbd8 25. Rc1 Qg4 26. Nd1.

Hmm, what do you think that Black should do here? All together now…

Position after 26. Nd1. Black to move.

FEN: 3r1rk1/ppb1n1p1/2p5/7p/3PPpqP/3Q3R/PP2N1P1/2RN1K2 b – – 0 26

PAWN BREAK!!!! The position is crying out for me to play 26. … f3! How could I miss it?

It’s perfectly set up. White can’t ignore the threats to take on e2 or f2. He has to take the pawn. He can’t take with the queen, obviously. He can’t take with the pawn, obviously. So there’s only one move to look at, 27. Rxf3. And then after 27. … Rxf3+ 28. gf Rf8, Black has tons of targets: f3, h4, the weak dark squares on the kingside.

Instead I played a move that was too slow, and White’s counterattack came like a punch from behind. I never saw it coming.

26. … Ng6?? 27. Qb3+ Kh7 28. Nf2 …

This surprised me because I thought it would just take on b7. As usual, I failed to understand what the computer was doing.

28. … Qc8 29. Rc5! …

And my jaw hit the floor. There’s no way for me to defend the h5 pawn!

29. … Kh6 30. Qf3 …

I’m just dead here. I might as well resign, but I played a couple more moves out of inertia.

30. … Ne5 31. de Bb6 32. Nxf4 Rxf4 33. Qxf4+ resigns

Well, I apologize you for showing so many mistakes. It is just a blitz game, after all. But I hope I have learned a lesson — to make the pawn breaks the first thing I look at, not the last.