The phrase “I should have won that gameâ€.

That's like asking if you could beat Nadal in tennis if you strike the ball correctly every time. No, he'd still outplay and humiliate you. Could you and your pub lads beat Liverpool if you managed to get a penalty? Of course not. They'd still outplay and humiliate all of you.

My thinking is roughly the following: “If two perfect players (or computers) played would they always draw? If not, why not? Does that mean that even if no mistakes are made at all that one side will still lose? If that is just because of only one person (or computer) having input on what is the “best” move, then what if two teams of 4 grandmasters each were made up and played one game, 4 for black and 4 for white with unlimited time and resources to come to a unanimous decision each move? Would they always draw? Is there even such a thing as the “best” move every single time? Obviously not, or else two perfect or very advanced computers would always play the same game. But in each non-draw game there must be a point where one side gains a lead and keeps it leading to victory. Or else all games would draw. So is it correct to say that in each non-draw game a mistake is made? How is that possible when there are computers that can calculate thousands of moves before deciding a move? Or if computers that can calculate every possible move ahead don’t exist yet then they surely will soon in the future. Does that mean the inevitable future of chess will be reduced down to a finite set of moves that will always end in a win or draw, whether played by person or computer?”
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Anyway, I guess getting back to the title of this post, if each non-draw game is the result of a mistake, then can someone really say, “I should have won that game”? I suppose every single player who ever loses should say that. If someone at a rating of 1000 plays a grandmaster, they will lose almost definitely 100% of the time, and it will be due to a mistake.
So, is it possible for a player rated at 1000 to play a game and think each and every move through enough to not make a mistake and therefore beat or at least draw against a GM? This is the main question I have, though I am happy to hear comments about the rest of my existential crisis as well... 🤗
To answer your primary question, with perfect play, chess is probably a draw.
As to the question of the title, I know I use that when I'm certain I was winning at some point and then didn't end up with a win. Sometimes it's used when a player is much higher rated and they don't end up winning as well
I had one of those "I should have won" situations in a recent tourney where I was up 3 pawns and my opponent didn't really have any compensation for that. However, I played a little poorly towards the end and had to accept a draw at the end, mainly due to time, but also due to the fact I didn't see a plan to convert the game in the time I had left.
A 1000 rated player is not familiar enough with enough patterns and themes to out calculate a much stronger player. If that had that ability, they wouldn't be rated so low. And humans don't have the processing power to play the way most engines do, so even if chess is solved by computers, there is still room for creativity and beauty within games.


A contrast to that is the process that Alexander Kotov describes in his book, “How to Think Like A Grandmaster”. He tells us about how he started to improve his game by going over famous games with complicated endings, and at critical points he covered up the players notes and spend hours analyzing to see what he thought was the best move and then uncovered the notes. He eventually saw improvement in his thinking and play.
I feel that computers have taken players away from getting really into the game and makes us just sit there going, “oh that was a bad move? Thanks computer.”
Hopefully you understand what I’m trying to say.

I think computers are useful for pointing out glaring errors; the minor evaluation changes aren't something most players are going to get use out of. When I run analysis, I only like at the evaluation value and then go to those moves)positions for deeper analysis.
You still have to develop the intuition and work on analysis and evaluation; to me, that's a pretty hard skill to develop.
I recently started getting back into chess and previously I really had only played in grade school and very rarely since then. This time around, I am doing a lot more studying and lessons and practice and analysis to really understand how to be better at chess, or try anyway. I keep coming across this deeply troubling feeling when I start to ponder chess and what it means to be “good” at chess. I keep having really tough questions pop into my mind.
My thinking is roughly the following: “If two perfect players (or computers) played would they always draw? If not, why not? Does that mean that even if no mistakes are made at all that one side will still lose? If that is just because of only one person (or computer) having input on what is the “best” move, then what if two teams of 4 grandmasters each were made up and played one game, 4 for black and 4 for white with unlimited time and resources to come to a unanimous decision each move? Would they always draw? Is there even such a thing as the “best” move every single time? Obviously not, or else two perfect or very advanced computers would always play the same game. But in each non-draw game there must be a point where one side gains a lead and keeps it leading to victory. Or else all games would draw. So is it correct to say that in each non-draw game a mistake is made? How is that possible when there are computers that can calculate thousands of moves before deciding a move? Or if computers that can calculate every possible move ahead don’t exist yet then they surely will soon in the future. Does that mean the inevitable future of chess will be reduced down to a finite set of moves that will always end in a win or draw, whether played by person or computer?”
I could probably go on for pages listing similar thoughts, but this basically leads to my deep concern: is chess really a game of beauty and art, a game that, as was the case after its introduction, rivals games of dice and luck, proving that we are the masters of our own fate and luck or destiny are false and free will and skill and talent and diligence are real? Or with enough computation power, will even this symbol of free will and determining the course of ones own life become reduced down to predestined “best moves” with no room for personal expression or beauty? Does technology kill our individuality and free will? If so, our free will is doomed as technology grows.
Anyway, I guess getting back to the title of this post, if each non-draw game is the result of a mistake, then can someone really say, “I should have won that game”? I suppose every single player who ever loses should say that. If someone at a rating of 1000 plays a grandmaster, they will lose almost definitely 100% of the time, and it will be due to a mistake.
So, is it possible for a player rated at 1000 to play a game and think each and every move through enough to not make a mistake and therefore beat or at least draw against a GM? This is the main question I have, though I am happy to hear comments about the rest of my existential crisis as well... 🤗