Chess players regardless of race, color, national origin, religion, sex, sexual orientation, gender identity or transgender status, age, disability, marital status, political affiliation or status as a parent can identify with the phrase when it comes to making a gross blunder or letting a won game slip away into a loss.
Who hasn't built up an overwhelming position with a huge material advantage or a robust attack, but the opponent stubbornly refuses to roll over and die? Or, our opponent makes a surprising sacrifice that may or may not be sound. Or, we just start drifting and at some point realize our advantage has all but evaporated.
Frank Marshall, who has been featured in a couple of recent posts, once wrote that "Winning a won game is the hardest thing in chess." It's not always easy to finish off an opponent and make them resign. Why is that?
First of all, when you have huge advantage there is often a tendency to think the game will be over shortly and that our opponent will soon resign. As a result we can end up overlooking a resource at his disposal, either obvious or hidden. And, when he plays it, it comes as a shock that leaves us shaken.
IM Jeremy Silman wisely observed that there are times it's a good idea that instead of trying to utilize one's advantage straightway, it may be wise to take time to curtail the opponent's counterplay before proceeding with one's own plans.
He notes that amateurs often get a permanent advantage like extra material or some static advantage
and then spoil their position by trying to force the issue. He recommends that first your position should be solidified and any chances for counterplay snuffed out before proceeding because a static advantage isn't going to go away.
Another reason for not winning a won game is our failure to realize exactly what our advantage consists of, or if we do know, not understanding how to take advantage of it. Then, too, sometimes a position can be tricky because it may appear that there are more than one or two roads to victory...and one of them might be wrong.
Yet another problem is fearing ghosts. One time I won a N early in the opening against a 2500+ IM and had an easy win. But then I started seeing threats that were not threats at all...they only existed in my mind. The result was that I lost the piece back and after that we were back on equal footing and I don't have to tell you the result. 
We are not out of reasons for failing to win won games yet! Average players have a poor knowledge of endings if they have any knowledge of them at all. All the experts tell us that there are several theoretical endgames that we simply must know, but few of us- listen.
Then there are miscalculations where we simply miss something and don't realize it until it's too late. Finally, there is always the gross blunder where we just hang a piece or overlook a one move mate.
In My Great Predecessors, Kasparov titled a chapter about Mikhail Tal as Bluff as a Weapon of Victory. Tal probably sacrificed more pieces and took more risks than anybody, but as Averbakh noted, Tal's opponents always had a win, but for some reason only in the analysis after the game. But, that wasn't always the case.
When Tal met Tigran Petrosian in round 8 of the Candidates tournament in Willemstad, Curacao in 1962, Tal played the most terrible game of the whole tournament.
In this game Tal didn't lose a won game because he never had one, but his play is a reminder that even the best players in the world are human and gross blunders can happen to anybody.
At the start of the game he left the well trodden paths of opening theory, but in a way that did not inspire confidence. Tal wrote that at move 8 he spent an hour trying to decide on two reasonable moves, both of which would give whim an advantage. Finally, he wrote down a move, then changed his mind and wrote down the other. By the way, two rounds later he played that move against Benko and won. A year later Spassky played the first move against Petrosian and also won.
Tal wasn't done writing down moves though. Because he couldn't make up his mind which of the two moves was better he suddenly made a third move which he described as ridiculous (actually, it wasn't that bad).
After a serious mistake at move 16 he stood worse. At move 19 he made a gross blunder, but Petrosian missed the best continuation and while his advantage was significant, it was not absolutely crushing. It didn't matter because Tal was having such a bad day that on move 20 he made another blunder and had to resign after Petrosian's reply.
Mikhail Tal - Tigran Petrosian
Result: 0-1
Site: Candidates Tournament, Curacao
Date: 1962
French Defense
[...] 1.e4 e6 2.d4 d5 3.♘c3 ♘f6 4.♗g5 dxe4 This move has long been the most common reply at the top level. It has largely replaced the old 4. ..Be7 5.♘xe4 ♘bd7 Also good is 5...Be7 6.♘xf6+ ♘xf6 7.♘f3 c5 Or, first 7...h6 8.♕d3 Tal played this on the spur of the moment. He called it ridiculous, but it incurs no great disadvantage.
20...♖xc4 White resigned.
8.♘e5 a6 9.c3 ♕d5 10.♗e3 cxd4 11.♕xd4 1/2-1/2 Robatsch,K-Geller,E/Havana 1963/MCD
8.♗xf6 gxf6 9.♗b5+ (9.♕d2 ♗d7 10.O-O-O is equal. Matanovic,A-Smederevac,P/Beverwijk 1965) 9...♗d7 10.♗xd7+ ♕xd7 11.♕e2 cxd4 12.O-O-O Short,N (2635)-Korchnoi,V (2625)/Rotterdam 1990 is equal and the game was eventually drawn.
8...♗e7 9.♗xf6 ♗xf6 10.♕b5+ Apparently this is the point of his 8th move. Often when the b-Pawn can be won in this manner it's at a cost. Here, however, white's marauding Q does not seem to come at a prohibitive cost.
10.dxc5 temporarily wins a P, but allows black a free game. 10...♕c7 11.c3 ♗d7 12.♕e3 ♖c8 13.b4 O-O 14.♗e2 b6 and black enjoys a slight advantage.
10...♗d7
10...♕d7 blocks his B and allows white to gain a small advantage after 11.♕xc5 b6 12.♕b5 and black has to allow the exchange of Qs leaving white with more space and the two Bs.
11.♕xb7 (11.♕xc5 ♖c8 12.♕xa7 ♖xc2 favors black.) 11...♖b8 12.♕xa7 ♖xb2 13.♗d3 cxd4 14.O-O One would think that white's passed a-Pawn would insure him of a long term advantage, but in reality the chances are about even thanks to black's better development and P-formation. Because the game can take many different paths here, I ran a Shootout, all of which ended in draws. 14...♗c6 15.♕a3 ♕b6 16.♗c4 This move hands over the advantage to black.
16.♕d6 keeps the position even. The best line of play is now 16...♗d5 17.♕xb6 ♖xb6 18.a4 ♔d7 19.a5 ♖b4 20.♖fe1 ♔d6 21.♘d2 ♔c7 Black ca stop the advance of the a-Pawn and the position is therefore quite equal.
16...♖b4 17.♕d3 O-O 18.a3 ♖a4 19.♖fd1 Stopping two squares short. 19.Rfb1 was much better.
19.♖fb1 ♕a7 20.♗b5 ♗xb5 21.♖xb5 g6 A safety precaution. 22.♘d2 ♖c8 Black has the advantage, but at least white is still in the game.
19...♕a7
19...e5 was also very strong. For example 20.♕b3 ♕a5 21.♘d2 e4 and all white can to is try to play moves that avoid immediate loss!
20.♖a2 This gross blunder loses at once.
20.♗b5 woud at least have allowed white to hold out longer. 20...♗xb5 21.♕xb5 ♖c8 22.♖a2 ♖xa3 23.♖xa3 ♕xa3 24.♘e5 ♕c3 Keeping the minor pieces on is to black's advantage.
24...♗xe5 25.♕xe5 ♖c4 26.♕b8+ ♕f8 27.♕f4 and the Q+R ending is much more difficult for black to play.
25.♘g4 ♗e7 Black is better, but white is still fighting. 20...♖xc4 21.♕xc4 ♗d5 22.♕xd5 exd5 is hopelessly lost for white. In Shootouts black scored 5 wins.
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