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Why do we “take a flier”?

Q: You were discussing the expression “take a flier” the other day on the Leonard Lopate Show. I think that it derives from the famous Flexible Flyer sleds and that “taking a flier” means taking a wild ride, taking a chance—just as we used to do when we were kids by sledding without helmets.

A: I like the sledding image, but I didn’t find any mention of the Flexible Flyer in my research on the expression. The Random House Historical Dictionary of American Slang gives several meanings for “take a flier (or flyer).” I’ve added a few parenthetical notes from the Oxford English Dictionary.

1. to place a bet or make a wager (the OED dates this to the 19th century);
2. to invest or speculate (ditto);
3. to make an attempt at something;
4. to make a suicidal leap;
5. to run off (OED: as far back as the 15th century, an escapee or fugitive was called a “flier”).