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For a period of about 400 years Spain issued coins denominated at 8 reales (ray-AHLS). The coins were large, similar in size to old-style US dollars but strangely enough there were few lower-denomination coins available when change was needed. The 8-reale pieces were very soft because they were made of almost pure silver, so to make change people would actually cut the coins into pieces - halves, quarters, and eighths, worth 4, 2, and 1 reale respectively. Thus the 1-reale piece became known as a "piece of eight".

These Spanish coins had a lot of historical effects because they were an almost universal medium of exchange. First, Spain sent ships full of them to supply the need for money in her far-flung colonies. That much wealth made the ships a prime target for pirates so pieces of eight became linked permanently with seafaring swashbucklers.

Second, the coins circulated even in the British colonies bordering on Spain's and continued to be used even after the US won its independence. The US silver dollar was designed with a similar size and weight so the two currency systems (dollars and reales) would be compatible. Even though Thomas Jefferson wanted a coinage system completely based on multiples of 10, a compromise was made to accommodate the use of pieces of eight when making change: instead of a 20-cent coin, the US system would have a 25-cent piece equivalent to a 2-reale slice. The American slang for a piece of eight was "bit", which soon led to quarters getting the nickname "2 bits" which is still occasionally used today. The two currencies circulated side-by-side for over 6 decades.

For mathematical reasons it's more efficient to make change with 20¢ pieces instead of 25¢ coins, but by the time reales were finally demonetized in 1857 the quarter denomination was so entrenched that it's never been replaced. Most other countries with 10-based systems (UK, NZ, Australia, EU, etc.) all have 20¢ coins rather than quarters.

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