Is it OK to Play a Losing Move in Order to Win?

Over two months ago, I wrote an article here, “9 lessons to learn from Bill Gates’ 9-move loss to Magnus Carlsen”, which generated a lot of discussion among my friends. I was also notified of something I hadn’t known when I wrote the article, which was that Magnus Carlsen only had 30 seconds for the entire game, so this was a severe constraint, and that he had explained that he does not usually play for “cheap tricks”. Unfortunately, the media sources that all my friends had sent me had not mentioned these important details. With 1 minute or 2 minutes, he could have played in a “normal” way, but 30 seconds is much less time.

I had been surprised that so many of my non-chess-playing friends thought (without the extra information about the constraints) that somehow, in general, it was OK to play for cheap tricks that could backfire: playing an objectively losing move in order to win a game against someone, hoping that the opponent would not see how to counter that bad move. I promised them that I would eventually write about why I thought that in general, I don’t consider it appropriate to play for cheap tricks that could backfire.

Ironically, recently I played a game in which I uncharacteristically used exactly a cheap trick in order to win a game. I will confess that I felt ashamed afterwards, and did not celebrate my victory. In fact, after the game ended, I slumped away back home feeling just as psychologically drained as after losing a game. At the same time, I would not have done what I did if I had not felt justified in what I did, even if it was not fully satisfactory. So I’ll use this experience as a way to discuss the issues surrounding playing a losing move in order to win.

Objectivity vs. subjectivity in chess: science vs. sport

The argument for playing “objectively” good moves is clear, I think. If the goal is improve one’s long-term playing understanding and performance, it is simply not good to play moves that you know are bad. You might succeed sometimes, against weak opponents, but against stronger opponents who can see just as well as you can, they will see your trick and punish you for the trick. I see a lot of chess play at lower levels in which trickery is attempted and often succeeds and often fails. Imagine playing tennis, and deliberately hitting a weak serve or return in hope of an unforced error. If your goal is not to just win a single game against a single opponent at a certain point in time, but to improve as an overall tennis player, I would say that it is better to try to do the “right” things.

The argument for playing “subjectively” good moves is also clear, however. In any single situation, you may have extra information that you can exploit. You might know that your tennis opponent has a poor backhand, in which you might place an objectively weak shot to your opponent’s weak side. As a matter of sport, in fact, it would be stupid not to use this information about the situation. And chess too is a sport: you may notice that your opponent lacks stamina and loses focus at the end of a long game, or has trouble playing quickly when time is running low on the clock, and use this information to your advantage. Psychology is a huge and valid element of the sport of chess, and goes well beyond these coarse examples, to the point of such subtleties as knowing whether your opponent likes to use Bishops in a certain way to control certain squares. Today, top professional chess players actually try to figure out their opponents’ psychology by performing data mining and statistical analyses on databases of the entire history of their opponents’ previously played games! In fact, arguably, Carlsen became the new World Champion recently by avoiding Anand’s preferred opening setups and types of positions, even at the expense of his own positions: in many games, he conceded objectively superior positions to Anand, as long as they were not what Anand expected to have.

So I would say that depending on whether you are treating chess as a serious discipline to continue improving at, or whether you have already practically maxed out in technical ability and/or are in a sporting situation where you evaluate the tradeoffs of taking a risk, it is justifiable to make different decisions.

But here at The Chess Improver, I try to focus on elements of chess that are objective in nature, because although psychology is always important, improving at objective fundamentals will always be most important until you reach a certain level.

The case of my game won by a cheap trick

Now it’s time for me to explain my cheap trick that won a game that was otherwise unwinnable.

Out of a superior opening as White, I went astray and blundered a Rook away for a Bishop on move 15. I have no excuse; I simply got my move order confused and got skewered. At this point, I had to start thinking about how to draw the game. I had some chances, having the Bishop pair against a Rook and Knight, and a passed Pawn on c5.

But my opponent played strongly, sacrificing the exchange back immediately in order to reach a position in which he was going to win a Pawn. On move 22, about to lose a Pawn and face a very difficult fight for a draw, I had to start thinking about swindling ideas in order to try to make the draw more within my reach. The trick is always to give the opponent more choices: good ones and bad ones. Often, playing a “good” move that has only one plausible reply, which happens to also be good, is just continuing the game along a path that you don’t want, and it is worth taking on some risk by playing a worse (but not yet losing) move that offers hope.

Step 1: fighting back to a drawn position

By move 27, I had swindled my opponent, through back rank threats, into a position in which I was still down a Pawn but had secured a drawn position. If I threatened to Queen my passed Pawn by pushing it to c6, then my opponent would have had no choice but to perpetual check my King, accepting a draw. So I had to think: now that I have secured the draw, can I still try to swindle a win out of a position in which I was still a Pawn down?

Step 2: attempting to get winning chances

Here’s when the time situation on the clock became quite relevant: my opponent was running very low on time, and was visibly anxious; he had 2 minutes left on his clock, while I had over 30 left on mine!! (It needs to be noted, however, that we were playing with a 5-second delay, which means that there is potentially enough time to play obviously moves in a simplified endgame position.) Meanwhile, my position was active enough that I didn’t have to accept the perpetual check right away: I was clearly no longer losing. Most important, however, was my tournament situation: I had lost my game in the previous round, and therefore I had to win this 5th round game in order to have any chance of catching the leaders by also winning the 6th round game. So I felt justified in beginning to play for a win. My only chance to win was to somehow prevent perpetual check and prepare a later advance of my passed Pawn on c5 to try to Queen it. It was a very long shot, but I had to try.

Step 3: playing the losing move in order to win

In order to take maximal advantage of the time situation, I had to play quickly myself, which I did, and unfortunately playing not so good moves. I actually ended up in a dangerous position by move 33. Here I had to pause and think. My opponent was down to less than a minute. Objectively the best thing for me to do was to acknowledge that I was now the one who had to defend and force a draw by perpetual check. I almost did this. It was the “correct” thing to do.

However, I embarked on a rare gamble. If I played a clearly losing move that lost my Bishop by force, it would cause my opponent to have to make “long” moves, reaching across the board and completely changing the nature of the position, and possibly disorient him. Then I could push my Pawn forward to c6 and try to get it c7 and then even to Queen. It was somewhat absurd to hope that this could happen, and I will confess that if not for the tournament situation, I would not even have considered this option. But given the tournament situation, and given that my opponent’s hand was trembling, it seemed that there really was some chance this swindle would work.

The swindle worked. My opponent ended up spending precious seconds, repeatedly, on a couple of moves, and then made the final blunder, which allowed me to trade Queens, resulting in a miraculous position in which his Knight and King were too far away to prevent my Pawn from Queening. In a lost position, with a few seconds left on the clock, my opponent allowed his flag to fall, and I won the game by time forfeit.

I marked my win on the posted paper sheet, quietly packed up, and went home.

Chess is a sport. I did not play well today, but I won. But sometimes, the reverse happens, and I play well, but lose.

The annotated game

Franklin Chen

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About Franklin Chen

Franklin Chen is a United States Chess Federation National Master. Outside his work as a software developer, he also teaches chess and is a member of the Pittsburgh Chess Club in Pennsylvania, USA. He began playing in chess tournaments at age 10 when his father started playing in them himself but retired after five years, taking two decades off until returning to chess as an adult at age 35 in order to continue improving where he left off. He won his first adult chess tournaments including the 2006 PA State Game/29 and Action Chess Championships, and finally achieved the US National Master title at age 45. He is dedicated to the process of continual improvement, and is fascinated by the practical psychology and philosophy of human competition and personal self-mastery. Franklin has a blog about software development, The Conscientious Programmer and a personal blog where he writes about everything else, including his recent journey as an adult improver in playing music.