Plot for the majority of the versions of Chess: Set during the Cold War, Freddie Trumper, The American, is playing a world championship chess match against Anatoly Sergievsky, The Russian. With Freddie is Florence Vassy, his chess second whose relationship with Freddie goes beyond professional boundaries. Anatoly's chess second is Alexander Molokov, who also happens to be connected to the upper levels of the KGB. Anatoly has a wife, Svetlana, but their relationship has become more and more strained over the years as Anatoly became more successful and more disillusioned with the political environment he is trapped in. Molokov sees the game as a chance for a Soviet victory over the Americans, attempting to coach Anatoly to make moves that have nothing to do with a chess board. Anatoly orders Molokov away and tries to think on his own, attempting to reconcile how he could have achieved the success he has always wanted and yet feel controlled and as if he has won nothing.
The man really in charge of the chess match is the Arbiter who acts as a referee. Although not bribable when it comes to chess, he is persuaded to allow gimmicky chess merchandise to choke the arena.
During the first game, Freddie storms off leaving Florence to try to pick up the pieces and justify his unjustifiable behavior. Florence and Molokov agree to bring their respective champions together for a meeting to find a resolution so the match can continue.
Florence and Anatoly arrive on time for the meeting, but there seems to be no sign of Freddie. After a brief awkward exchange, they find themselves being drawn to each other, discovering that the political enemy may not be an enemy at all. Freddie bursts upon the incriminating romantic scene and loses his temper. To him, the Communists are the enemy. He feels that Florence should completely share this point of view. When Florence was a young child, the Soviets forcefully took control, causing her to emigrate and leave her father behind. She can barely remember her father now, and has no idea if he is alive or dead.
Florence takes Freddie's outburst at the meeting as one too many childish, self-centered tantrums for Florence to deal with. This time she is leaving him for good. Her decision shatters Freddie, and he loses the match. Like Florence, Freddie too has had a painful childhood. His father walked out when he was twelve, and his mother proceeded to take on a series of lovers. Freddie concentrated on chess and ran away as soon as he could, never to contact her again.
It turns out that Anatoly has won a lot more than just the match. He has gained his freedom from Soviet control as he is defecting. He has also won Florence who has now become his lover.
Anatoly has to defend his title a year later against a Soviet challenger. The Soviet government is desperate to get him back, and once again Molokov is deployed. Molokov uses Svetlana to try to pressure Anatoly into throwing the match (allowing the new Soviet challenger to win) and return to Russia. Molokov also contacts Freddie, claiming that he has information about Florence's father he can give her only if Anatoly cooperates.
Freddie is desperate to get Florence back into his life. Florence wants nothing more to do with him.
Florence is not coping well with the existence of Anatoly's wife, and Anatoly is too troubled by his own thoughts to comfort her. He ultimately decides that he has to lose the game and return to the Soviet Union, mainly for Florence and her father. He intentionally makes a wrong move, and loses the match. He returns to the Soviet Union with his wife, although he and Florence are certain that they will never stop loving each other. Despite Anatoly's sacrifice, the only party to receive a real benefit is Molokov on behalf of the Soviet Union. Molokov never had any real information about Florence's father.

One of the things that makes Chess so popular is that the characters are very human, and generally avoid stereotypes. (The American is rather stereotypical with his egomania and Russian-hating, but he is given "Pity The Child" as a partial explanation for his behavior.) It is The Russian and Florence's frustration at the politics behind chess that brings them together. The Russian is surrounded by those capitalizing off his talents, who "call me their friend / I hardly knew them". Florence refuses to take part in The American's childish games. Both The Russian and Florence are amazed when they find that the enemy really is not ("You are so strange, why can't you be what you ought to be? You should be scheming, intriguing, too clever by half"). "Nobody's Side" is packed with wonderful couplets, and "Heaven Help My Heart" is a beautiful song depicting Florence's state of affairs. "Pity The Child" is a great song, even though it doesn't make up for The American's behaviour -- he sings "pity the child but not forever, not if he stays that way". Chess is very dark, portraying a world where you can trust no one and love can not survive. Perhaps it sums things up best in the line: "But we go on pretending stories like ours have happy endings".
Lyrical quotes from Tim Rice's libretto for Chess.
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