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I found the phrase, “he’s always playing chess when others are playing checkers,” in today’s (September 11) article of the New York Times, written by Charles Blow under the headline of “It’s a Mad, Mad, Mad, Mad World.” It reads;

The Syrian debate is too serious to be subjected to the rules of Washington’s game, even as it must be conducted by its gamesmen. It has broken down the normal tribalism of left-right, liberal-conservative constructs, and mixed folks into maddeningly contradictory coalitions.

On one side are some of President Obama’s staunchest supporters, who are always convinced that he’s the smartest man in the room, that he’s always playing chess when others are playing checkers.

Without consulting a dictionary, I can assume that “playing chess” requires strategic thinking and in-depth analysis of the situation as compared with “playing checkers," of which the scenario is more simplistic and easier to play.

The Marc Ensign website makes this distinction:

While checkers is primarily played in the moment, chess requires a complex strategy that is often won by thinking ahead.

Though I haven’t checked any English dictionaries yet, Google Ngram doesn’t show any incidence of “play chess when others are playing checkers.”

What is the currency of “play chess when others are playing checkers.”？Is it a well-used and well-received phrase?

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    Sorry, but to me, your last paragraph just comes off as pretentious ad hominem logic.
    – iterums
    Commented Sep 12, 2013 at 8:00
  • @iterums.I simply wanted to add that I like this turn of phrase. The last line was a joke and I didn't mean it. But it wasn't necessary to my question. I cut it off per your advice.
    – Yoichi Oishi
    Commented Sep 12, 2013 at 8:33
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    There are ways you use the phrase in an office setting without sounding pretentious. (1) You could be a bit self-depricating, like when you are complimenting coworkers on their knowledge of something, particularly if you don't understand it very well: I feel like I'm playing checkers while you're all playing chess. (2) You could include yourself when the subject is a plural pronoun. For example, in a meeting, if you think a team is dancing around the heart of a matter and needs to get more focused, you could try, I feel like we are all playing checkers when we should be playing chess.
    – J.R.
    Commented Sep 12, 2013 at 9:12
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    As an aside, I'd just like to mention that this is an American phrase, as in the UK we call "checkers" "draughts"; and it doesn't have quite the same ring to it without the alliteration!
    – WheretheresaWill
    Commented Sep 12, 2013 at 9:49
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    The phrase could also be used to suggest that someone is over-thinking a problem, although that is not the sense in the article you cite.
    – bib
    Commented Sep 12, 2013 at 11:30

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Yes. I have heard it many times and often in sports. It means that the player that is "playing chess" is on their game and that they are outwitting their opponents. There is definitely some heavy yet subtle connotations in this phrase. The person playing chess is considered smarter than his opponents. It is both a way to praise the person playing chess and to a certain extent put down the person/people playing checkers.

Common Usage: "Peyton Manning (very good American football quarterback and considered one of the smartest men in football) is on fire tonight. He knows exactly where the other team is going to line up. He is playing chess and they are playing checkers."

I would say American football lends itself to this phrase since it has a dimensional chess like quality to it.

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