From Wikipedia: The sign is first attested in British, American, Canadian, Mexican and other Spanish American business correspondence in the 1770s, referring to the Spanish American peso, also known as "Spanish dollar" or "piece of eight" in British North America, which provided the model for the currency that the United States later adopted in 1785 and the larger coins of the new Spanish American republics, such as the Mexican peso and the Peruvian eight-real and Bolivian eight-sol coins.
The best documented explanation reveals that the sign evolved out of the Spanish and Spanish American scribal abbreviation "ps" for pesos. A study of late eighteenth- and early nineteenth-century manuscripts shows that the s gradually came to be written over the p developing a close equivalent to the "$" mark
One explanation is that the Spaniards, who first colonized America, used a dollar called a "piece of eight," as it was worth 8 reales. The original symbol for this coin is said to have been /8/, the lines on each side of the figure serving to distinguish it from an ordinary arithmetical 8. Later on the two lines were drawn through the figure $. And later still this was altered into $. Another explanation traces the symbol back to the Pillars of Hercules, the arms of Cadiz, in Spain, adopted by Charles the Fifth of Spain, and stamped on "pillar pieces", which were exported to America. The two pillars of the design were joined by a scroll turned round them.
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