Heads I Win, Tails You Lose


This one fooled me. Heads I win, Tails you lose.

There’s just something so American about that phrase, so contemporary. I can imagine Bogie uttering it, straight-faced, just before turning the tables on some sleazeball.

So I was surprised to find a FirstMention for Heads I win, Tails you lose in the London Times, dating back to October 28, 1822. [but see the addendum, below!]

But what was he?–a professed gambler: one who had been initiated at Paris in all the mysteries of the craft: who played a safe game — when he won, he walked away — when he lost, he brought his action. This was his game–“Head, I win; tails, you lose.”

The context for all this is a bankruptcy hearing in the Court of King’s Bench in Westminster, which I gather was (and is) the high court of the land.

So when you next hear “Heads I win, tails you lose”, think pence and farthings rather than nickels and quarters.


Well, I was half right. Looks like this has American roots after all. Here’s an 1802 FirstMention in the Congressional Record of February 1, 1802 as reported in the September 2, 1802 edition of the National Intelligencer and Washington Advertiser.


Our FirstMention research is carried out in many sources, including historical newspaper archives, online family history records, state archives, and old books.