Word.ws English Dictionary

heads I win, tails you lose

heads I win, tails you lose phrase: said to describe a conflict in which someone has a particular advantage from the start.

Phrase

heads I win, tails you lose

  1. Said to describe a conflict in which someone has a particular advantage from the start.
    • I suppose it is just as if he had said to me, "Heads I win, tails you lose." I thought that it was against law; but this man, Lord they call him, quieted me with his reciprocity.1790, Sir David Dalrymple, The Little Freeholder, a Dramatic Entertainment, in Two Acts, page 31
    • I'll flip a coin, heads I win, tails you lose—and the loser must tell a story1922, Jim Tully, Emmett Lawler, page 163

Origin of heads I win, tails you lose

A slight twist on the normal convention when flipping a coin, which is heads I win, tails you win. The flurry of antonymic reversals — heads or tails, you or me, win or lose — sounds euphonious and might seem fair upon first hearing, which makes the phrase suitable for a fast-talking confidence trick except to the extent that it has become hackneyed and synonymous with rigged arrangements.

Questions about heads I win, tails you lose

What does heads I win, tails you lose mean?
Heads I win, tails you lose means said to describe a conflict in which someone has a particular advantage from the start.
What part of speech is heads I win, tails you lose?
Heads I win, tails you lose is a phrase.

Words near heads I win, tails you lose in the dictionary

  1. heads
  2. heads and thraws
  3. heads down
  4. heads down, thumbs up
  5. heads for the hills
  6. heads I win, tails you lose
  7. heads in the clouds
  8. heads in the sand
  9. Heads Nook
  10. heads of agreement
  11. Heads of Ayr

Source and license

Adapted from Wiktionary: heads I win, tails you lose (page history and authors). Text available under the Creative Commons Attribution-ShareAlike 4.0 license. Word.ws reformatted the entry and added links. Wiktionary data of 2026-09-02.

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