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In the story, Bunnish, one of the members of the chess team, (I think it was a high school chess team) becomes rich and seclusive, and invites the other members of the team to his mansion to replay a game that he (Bunnish) lost in high school.

In the end of the story, it is revealed that Bunnish has invented a time machine, which allows the traveler to go back in time and create a new timeline, causing the traveler to "die" in the original timeline the moment that he activates the machine.

Bunnish has been using the time machine in a sort of infinite loop to repeatedly go back in time to the middle of the game that he lost. (Of course, he always loses.)

The story was in an anthology of science fiction short stories about chess.

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  • You have a good start here but can you take a look at this guide to see if there is anything else you can edit in? For example, when do you remember reading it?
    – TheLethalCarrot ♦
    Mar 27, 2018 at 9:20
  • @TheLethalCarrot not quite needed given there's character names and a pretty good description, in fact with the character name alone this story likely is (and was) uniquely identificable.
    – Edlothiad
    Mar 27, 2018 at 9:23
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    I really need to see the movie "Chess Club Time Machine".
    – T.E.D.
    Mar 27, 2018 at 13:30

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Unsound Variations by George R R Martin All the details seem to match (sorry, not got time to write a longer answer) It appears in the anthology 'Pawn to Infinity' Review here:

Four friends from a decade past chess team, the B team at that, at the University of Northwestern reunite under absolutely no pretense at all. They haven't kept in touch over the years nor were they particularly close back in the day. An invitation is extended and they all inexplicably decide to attend. ( And we are all aware of the horror of these kinds of reunions…) The host, Bunnish, is the only one of the four to be met with any kind of success in life and has become exorbitantly wealthy dealing in electronics. Delmario, has had brilliant ideas, but always beaten to the punch by Bunnish and now has only alcohol to keep him company. E.C. Stuart has had every sound business decision he has ever made work against him and now revels in a life of mediocrity. And Peter has suffered a life of failure in every creative endeavor he has ever pursued.

[...]

Using a time travel machine of his own device (roll your eyes here) Bunnish has successfully ruined the lives of his three teammate and the person at UC who beat him. Apparently, he never once has considered going back to alter the game so that he might win.
Review of the book

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  • And the last of the invited 'friends' realizes at the end that while the past is over and done with, Bunnish can't screw him over in his future endeavors.
    – Jeff Zeitlin
    Mar 27, 2018 at 11:22
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    I seem to recall that he was a passive observer for the earlier part of each of his restarted lives, so he could not change the chess game (the author considered that factor). I think the active portion of the restarted life may have begun when the time machine was used, i.e., using or not using the time machine was a universe bifurcating event; this makes some of his accomplishments seem less plausible. If the active portion began when the first choice was made, the story makes more sense but is a poorer fit with quantum theory.
    – Paul A. Clayton
    Mar 27, 2018 at 12:30
  • The achivements would be more plausible if the machine had 3 states: completely inactive, primed, fully activated, and activating the third state sent him back, but he remained a passive observer until the point where he 'primed' the machine. Making the early part of each reset a torture as he sees events he can't alter unfold every time.
    – Chronocidal
    Mar 27, 2018 at 15:09

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