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Regarding the phrase:

Breaking windows with guineas

What is its meaning, and origin?

The 'guineas' part of it might mean more to the British audience on this site than the others.

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FWIW, a guinea is a pound plus a shilling, for lots of excellent reasons... –  ukayer Feb 10 '12 at 5:24

2 Answers 2

During the Seven Years' War (1756-1763), Britain's ruinously expensive naval sorties against France were actually inflicting very little damage. In the specific case of the Sept 1757 Raid on Rochefort, British MP Henry Fox said it was like breaking their windows with guineas (i.e. - using and thus losing our most valuable coins as missiles, simply to break their glass windows).

It's really just a little-known quaint archaism. You're more likely to hear Cut off your nose to spite your face today.

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I wouldn’t say that “cutting off your nose to spite your face” has quite the same meaning. “Throwing money down the drain” probably comes closer. –  Brian Nixon Dec 18 '11 at 16:59

To add to what FumbleFingers says: the phrase was coined by politician Henry Fox during the seven years' war to ridicule William Pitt and the British government that was spending quite a lot of money for very little results against the French.
I have found an academic paper on the subject... it's in French.

I had never heard or read the phrase before. As to whether "cut off your nose to spite your face" really means the same I wonder. Couldn't we say "kill a fly with a sledgehammer"?

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Fly with a sledgehammer means a disproportionate response, this is more that the response costs more than the damage. Closer is probably some US general's quote about Afghanistan - sending a million dollar missile to blow up a tent –  mgb Dec 18 '11 at 17:52
    
I'm a bit surprised both you and @Brian Nixon in his comment to my answer don't think "cut off your nose..." has the same meaing. To my mind, the whole point of both expressions is that the aggressor is actually being damaged/losing money. "Swatting a fly with a sledgehammer" might be way over the top - but unless the fly is actually on your body at the time, you probably won't suffer unduly from the disproportionate action. –  FumbleFingers Dec 18 '11 at 18:01
    
@FumbleFingers: They both express similar ideas, but I feel there's a subtle difference. "Breaking windows with guineas" would (though I've never heard it "in the wild") suggest to me an attack so inefficient that it's costing you more than its effects are costing the target; the solution is either to stop or to find a cheaper way to do it. "Cutting off your nose" is more about a situation where the action itself, no matter how well and cheaply carried out, will end up hurting yourself, much like (more specifically) "sawing off the branch you're sitting on". –  Ilmari Karonen Dec 18 '11 at 20:35
    
Many thanks to all, I think I get all the nuances now (concluding with Ilmari's balancing act) and will go back to the debate where it is being used –  pekka luoma Dec 18 '11 at 23:13
    
like (more specifically) "sawing off the branch you're sitting on". – Ilmari Karonen 3 hours ago... Did not see this part of it, which is far too general; I was thinking that this " the whole point of both expressions is that the aggressor is actually being damaged/losing money" from FumbleFingers was right on the ball? –  pekka luoma Dec 18 '11 at 23:50

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