Rueben Fine seemed to be plagued by bad luck. In his personal life he was married and divorced three times and in his chess career he tied for first place with Paul Keres in the prestigious 1938 AVRO tournament in the Netherlands, but Keres placed first on tiebreaks. The tournament was organized with the hope that the winner would be the next challenger to Alekhine. Fine, who got off to a tremendous start, won both of his games against Alekhine, but then lost in round seven to Keres and this wound up as the decisive game because it gave Keres the superior tiebreaks.
After World War Two ended Fine was invited to participate in the tournament to determine the successor to Alekhine who had died, but he declined for reasons that are the subject of speculation even today.
His luck was no better in the U.S. Champioships. Once when asked why Fine never won the U.S. Championship, Samuel Reshevsky replied, "Because I was playing." But, even when Reshevsky wasn't playing Fine's luck was no better. In the 1944 Championship Fine scored 14.5-2.5, but finished a half point behind Arnold Denker who played the tournament of his life to capture the Championship. Fine's only loss was to Denker
Fine's U.S. Championship woes began in the first Championship in 1936 when he only managed to tie for 3rd-4th with George Treysman behind Reshevsky and Albert Simonson. Fine suffered only one defeat...against Simonson, who's only previous claim to fame was a mediocre performance on one of the U.S. Olympiad teams, but in this event had the best result of his career.
The second Championship was held in 1938 and Fine's luck wasn't any better. Fine had made a name for himself in Europe where he lived much of 1937-1938. After tying for third place with Reshevsky at the Nottingham tournament in 1936, he had finished first at Moscow, Ostend, Margate and Stockholm in 1937 and then tied for first prize ahead of all the world's best players at the AVRO super-tournament. Also in 1937 he had been selected by world champion Max Euwe to be his second in Euwe's title defense against Alekhine.
Thus, in the 1938 U.S. Championship Fine, Reshevsky and Kashdan were the favorites. Reshevsky soon assumed the lead, but Fine stayed close all the way to the end even though he lost two games to Reshevsky's none. Fine lost to Anthony Santasiere, but it was likely his loss to school teacher Milton Hanauer that cost him the tournament. In that game Fine came within one move of winning, but made a disasterous blunder. Hanauer, who finished tied for 12th-14th out of 17, had a horrible position and one move by Fine would have forced the win, but Fine overlooked a simple refutation to what appeared to be a Hanauer threat and so selected another move instead. The ending looked to be about equal, but Fine's subsequent play was weak in that it allowed Hanauer too much play. Hanauer went on to win and so Fine lost a very valuable point to an also-ran.
The third Championship was even worse. It was the last to bring Fine, Reshevsky and Isaac Kashdan together and even though all three remained active they never again all competed in the same title event. Reshevsky described the 1940 Championship as a personal duel between him and Fine and their last round game against each other was the big story as it determined first. Fine had lost only one game, to the super-solid Abraham Kupchik, but then piled up 10 wins and four draws. Going into the last round Reshevsky had a half point lead, so all he need was a draw to gain the title.
Fine, playing white, began with a psychologically good choice of opening: he played the 4.Ng5 variation in the Two Knight's Defense and Reshevsky was virtually forced to sacrifice a Pawn. This put Reshevsky in a situation where he had to play a sharp position when he would have preferred a quiet one.
By move 16 Fine was a bit better developed and had excellent prospects in the form of the two Bs and superior P-structure. At the same time, Reshevsky had a N out of play but his other pieces were active. Then on move 17 psychology began working against Fine. By exchanging pieces he could have gotten excellent winning chances, but at the same time it would have created Bs of opposite color and given Reshevsky drawing chances which Fine wanted to avoid. So, instead he made a promising but unnecessary exchange sacrifice. It looked like it was going to be successful because on his 21st move Reshevsky played a move that brought him to the brink of defeat. Indeed, Fine's next move demonstrated that Reshevsky was near defeat and by move 25 he was desperate. Two moves later Fine needed only to play 27.Rf4 and the U.S. Championship was his.
However, Fine saw a move involving three forcing moves followed by the killer and played his B to f4 instead of his R. Reshevsky later said a miracle had happened. All went according to Fine's plan until they reached move 30. That's when Fine realized to his horror that Reshevsky had a refutation to his intended move and there was nothing better than to play an alternative that only lead to a draw. Once again, a single move had cost his the title.
Here is Fine's depressing loss to Hanauer.