...who would have won? In 1941, Paul Keres wrote an article for Chess Review in which he discussed the question.
Apparently Keres could still address the question because he wrote the article before the Germans invaded Russia which happened on June 22, 1941 and the US didn't enter the war until early December.
At that time the leading players were Botvinnik, Capablanca, Euwe, Fine, Flohr, Reshevsky and Keres himself, so the question as to who should challenge Alekhine was a difficult one.
The general opinion was that Alekhine, although he was world champion, was no longer among the best players in the world. During the years of his incredible successes which stretched for several years before his match with Capablanca in 1927 to several years afterward, Alekhine had convincingly demonstrated his superiority over all his rivals.
But, as Keres observed, Alekhine could not remain at such heights forever and he had started to descend as was evidenced by his 6th place finish at Nottingham 1936 and his tie for 4th at AVRO in 1938. Then there was his loss of his title to Euwe in 1935 even though he won it back in brilliant fashion in 1937. Thus, talk was circulating about the end of Alekhine.
Nevertheless, it was Keres' contention that such talk was wrong because Alekhine's failure to win at Nottingham and AVRO did not imply that he played weaker than his rivals nor did his triumph over Euwe mean that he played stronger than any other candidate.
Keres pointed out that tournament success depends not only on chess ability, but on numerous other factors whose influence is very great at times and, as a result, it would be wrong to judge the strength of a player by isolated tournament results. It's also necessary to take into account the personal experience of previous meetings with the same players and only by taking all factors in conjunction can a more or less accurate picture be obtained.
Had Alekhine's playing strength declined compared with the period of his greatest successes? And, at the same time had the strength of his rivals risen?
Reshevsky once stated that he did not believe Capablanca's strength had fallen off later in his career, but he was less dominating because the strength of his rivals had increased. Keres believed that while there had been some decline in Alekhine's strength, possibly due to age, fatigue or other reasons, he was not weaker than anyone of his potential challengers. His original ideas, fighting temperament, colossal resourcefulness and ingenious tactical ability had not diminished.
At the 1939 Buenos Aires Chess Olympiad, Keres had an opportunity to analyze with Alekhine and wrote, "I can freely declare that none of his seven rivals possesses his resourcefulness, his most subtle grasp of positions and his experience."
Given that, what did it take to defeat Alekhine? A fundamental theoretical knowledge, accurate play, and above all, greater endurance and stronger nerves. Keres concluded that in a match against any of Alekhine's likely challengers the outcome could not be determined in advance.
So, what about the chances of Alekhine's challengers. Euwe was out, not because of lack of ability, but because Holland was in the war zone.
AVRO not withstanding, according to Keres, Fine was inferior to Alekhine in resourcefulness and in grasping the hidden nuances of a position; nevertheless, he surpassed him in endurance, strong nerves and possibly in opening knowledge. In any case, a match with Alekhine, while it might be interesting, was hardly possible given that Fine was second behind Reshevsky on the US chess scene.
Of the others, another match with Capablanca seemed out of the question because they were so distrustful of each other. Flohr had an outstanding mastery of positional play and he was at his best in the opening and ending, but his defect was that he had become over cautious and preferred defense to attack.
Keres modestly admitted that while he had a good tactical ability he did not possess sufficient positional knowledge and his endgame play still required deeper study. Also, like Alekhine, he disliked the strategy of waiting and in tedious defensive positions he felt bored and often played them badly. In a match against Alekhine he could not predict the outcome, but stated, "it would not be cat and mouse play."
Personally, Keres believed Alekhine's most serious rival was Botvinnik because he had an excellent knowledge of theory, utilized with extraordinary precision the slightest positional advantage and excelled in defense. Keres believed that if Alekhine could not gain the advantage early on in a match his nerves might give out.
Alekhine himself once addressed the same questions as Keres. He expressed the opinion that in view of Reshevsky's successes there could be no doubt that he had sufficient abilities to seek the world title.
Alekhine wrote that before 1940 he was certain that Botvinnik and Flohr wanted a shot at the title, but for various reasons matches against them could not be brought about. He felt Keres seemed willing to let a few years pass before making any challenge. Presumably based on his own opinion of his chances previously mentioned, Keres believed he needed more time in order to mature. And Fine had pretty much decided to concentrate on his career in psychiatry.
For his part, Alekhine stated that he would relish a match against either Botvinnik or Reshevsky, adding that there would surely arise battles that would excite interest.
But, this post is about Reshevsky, who Keres claimed was hardly inferior to Alekhine as to wealth of original ideas, he played extremely well in time pressure and he conducted the ending with amazing skill.
Reshevsky had some vulnerable points though.
One area of vulnerability dating back to his days as a child prodigy was his sense of superiority over his opponents which he had apparently retained in his subconscious to the present day. As a result, he always endeavored to confront his opponent with the solution of some problem and to direct the course of the game as he deemed fit. However, the position does not always warrant such play, especially when one's own position has become worse. This factor constituted a great danger to Reshevsky. The opening was his weakest point and it was not possible for him to correct that weakness and bring it up to Alekhine's level in such a short time.
With the US entering the war and Alekhine's death on March 24, 1946, there was never any possibility of such a match taking place and by the time the war was over Botvinnik had become invincible.
Here is a game they played in Kemeri 1937 in which Alekhine unleashes an amazing combination. In the tournament Reshevsky shared first place with Vladimir Petrov and Salo Flohr while Alekhine shared 4th and 5th with Paul Keres.
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