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I understand that it means "to extract money from someone". But what does pip refer to here? What's the image behind this phrase?

Bonus question: Is there a relation to the word "pipsqueak"?

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As suggested by the Word Detective pips refers to fruits seeds:

Until the pips squeak:

  • To “squeeze (someone) until the pips squeak,” meaning to exert heavy pressure on someone in order to extract money, information or simply obedience, is definitely a reference to the “pips” in a fruit.

  • The sense is that if a fruit is squeezed very strongly the pips would shoot out, perhaps at least figuratively, making a “squeaking” sound as they fly across the room.

  • The term first appeared in print in reference to the heavy reparations demanded from Germany after World War I (“Dealing with the question of indemnities, Sir Eric said: The Germans, if this Government is returned, are going to pay every penny; they are going to be squeezed as a lemon is squeezed — until the pips squeak.” 1918).

Pipsqueak appears to have no relation to the above saying:

  • Curiously, the epithet “pipsqueak,” meaning a weak and/or insignificant person, seems to have no real connection to “make the pips squeak.” Although it appeared about the same time (1910), “pipsqueak” employs “pip” in the sense of “something very small” and “squeak” in the sense of “small, weak sound” to convey the sense of a young child or powerless adult who can only squeak in protest.

(The Word Detective)

Its origin, though often attributed to Churchill, is actually from Sir Eric Campbell-Geddes, who served as First Lord of the Admiralty (civilian head of the Navy) in 1917-19.

  • We will get everything out of her that you can squeeze out of a lemon and a bit more.... I will squeeze her until you can hear the pips squeak. My only doubt is not whether we can squeeze hard enough, but whether there is enough juice.

(Said of German war reparations following World War I by Sir Eric Geddes (1875-1937), British Conservative politician, in December 1918 at the Guildhall, Cambridge, England.)

  • It was re-used by Denis Healey, Chancellor of the Exchequer, on presenting budget to Parliament in May 1978; [It will] squeeze the rich until the pips squeak.

(The Phrase Finder)

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  • Good work, Mr. Josh. Funny that, re the pipsqueak.
    – Lambie
    Apr 30, 2017 at 20:28
  • The Denis Healey quote is well remebered from the time when he was Chancellor of the Exchequer in Prime Minister Harold Wilson's governement when the rich were taxed at a rate of 19/6-in the Pound. This was back in the 1960's. Lord Hailsham, former Lord Chancellor of the House of Lords & titular head of the Judiciary, once referred to the splendid Denis Healey as: "A piratical old bruiser, with appalling manners and a first-class mind". May 1, 2017 at 10:03

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