2/2/2025 – When should you take the plunge on a risky move? GM Jon Speelman explores this question by diving deep into a single position from his recent 4NCL game against IM Richard Palliser. Analysing a critical moment in the Caro-Kann, Speelman weighs the dangers of a bold knight leap and the fine margins between courage and calamity. His conclusion? Sometimes, the gamble is worth it — especially if the worst outcome is losing in style.
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Trust yourself
[Note that Jon Speelman also looks at the content of the article in video format, here embedded at the end of the article.]
This month I'm looking at just a single game and indeed really just a single position in detail in order to consider when it is reasonable to play a move if you have some suspicion that it might lose.
It's from the 4NCL last weekend, where on the Sunday I was Black against Richard Palliser, a strong IM who is the editor of CHESS Magazine, writes for Popular/Everyman Chess and was the next really strong chess player to follow me at Worcester College Oxford.
The game is an exf6 Caro-Kann in which, having edited some analysis recently, Richard decided to play an immediate Be3, a move championed by Wesley So amongst others, which aims to play c2-c4 in one move, rather than going c2-c3 and c3-c4 later.
The full game appears, of course, in the pgn, and I have no great pretensions about the accuracy of our play up to this diagram, where I had to decide whether I could play 13...Ne6.
I wanted to play ...Ne6 because I was put off by 13...Bd7 due to 14.Bg5 Qg6 15.Bf4 Bxf4 16.Qxf4 when the move I wanted to play, ...Ne6, loses a pawn to 17.Qxf5 since none of the tactics work for Black. But actually engines don't much mind 16...Rac8 rather than 16...Ne6, or indeed 13...h6 instead of 13...Bd7.
In any case, I started looking at 13...Ne6 and in the way of the world, neither Richard nor I noticed 14.Ng3, which is actually quite dangerous. In our defence, we are carbon-based and it was Sunday morning. The game continued as expected: 14.d5 cxd5 15.cxd5 Nc5, and Richard played the very natural 16.Bg5 Qg6 before he had to make a massive decision.
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White has a single move before Black can connect his rooks and get a very decent position, so you have to look at the only move which gains a tempo: 17.Nf4.
When I first looked at Ne6 I thought, "Oh blast" (other expletives are available and more verisimilitudinous), because of 17...Qxg5 18.Rxf8+ Kxf8 19.Ne6+, but then I realised that ...Nxe6 defends the queen and wins.
I carried on looking and found 20.Ne6 Nxe6 21.dxe6 Qxd2 22.e7, which is a lovely idea, but luckily for me, loses outright to 22...Qe1+ 23.Bf1 Qxe7!.
And I explicitly analysed one other line - 20.b4 Nxd3 21.Rxf8+ Kxf8 22.Ne6+ Bxe6 23.Qxg5 Bxd5 24.Qxf5 Re8! 21.h3 (actually the engines prefer h4) 21...Be4 - which I thought should be winning for Black, though in fact after 26.Qd7 Ne5 27.Qd4 Nc6 28.Qc5+ Ne7 29.Qxa7 b5 White is fighting. In any case, Black is trying to win, so there is absolutely no reason not to allow Nf4.
I did also notice that White might have 20.d6 (see next diagram) to threaten 21.Nd5 and this is, in fact, the correct move, but I thought that h6 was probably a decent defence and that, given that I started a whole piece ahead, I ought to have something reasonable. If he did have some beautiful forced win and found it, then I would lose a splendid game, but it seemed a decent gamble that this wouldn't happen. There was reasonable doubt about White's winning chances, so I played the move that I wanted to.
Here Black has three main moves: ...h6, which was my first thought though of course I hadn't yet noticed the Ng6 trick, ...Qf6 and ...Nxd3. In fact, all three seem to lead to defensible positions, which I suppose vindicates my judgement that I wouldn't be losing if he played Nf4.
After a long think, Richard, I'm sure reluctantly, abandoned Nf4 in favour of the sensible move Nd4. I thought I'd get some advantage afterwards, but in fact it was equal, and there was one move later, when I pressed my luck and he could have got some advantage. Having realised this, I hastened to exchange queens and offered a draw - which he accepted.
The main lesson today is to trust yourself. Even if your opponent has a very dangerous-looking line you can try to analyse it to the best of your ability to decide whether you have a defence and if you believe so and it's really the move you want to play, then perhaps you should do so. The worst that can happen is that you lose a brilliancy.
Select an entry from the list to switch between games
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Jonathan SpeelmanJonathan Speelman, born in 1956, studied mathematics but became a professional chess player in 1977. He was a member of the English Olympic team from 1980–2006 and three times British Champion. He played twice in Candidates Tournaments, reaching the semi-final in 1989. He twice seconded a World Championship challenger: Nigel Short and then Viswanathan Anand against Garry Kasparov in London 1993 and New York 1995.
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