heads I win, tails you lose en · X
Etymology
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.
Meanings
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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:So here was an early instance of the "heads I win, tails you lose" dilemma, in which the United States is faced with corrupt regimes, on the one hand, and Islamic militants, on the other—or indeed a collusion between them.
2011, Christopher Hitchens, Arguably: Selected Essays, page 14:I'll flip a coin, heads I win, tails you lose—and the loser must tell a story
1922, Jim Tully, Emmett Lawler, page 163:
Relateds
moral hazard · lose-lose · house advantage · Dutch book · the house always wins