25 Dollars - Elizabeth II Independence

Anguilla's 1968 coinage is one of the more unusual episodes in Caribbean numismatic history. Following the forced federation with St. Kitts and Nevis, Anguillan leaders staged a revolt in May 1967, expelled the St. Kitts police, and unilaterally declared independence — a secession Britain refused to recognize. The resulting coins, struck without Crown authorization, occupy a legal grey zone: issued by a self-declared government that technically did not exist under international law at the time of striking.

Britain eventually sent paratroopers in 1969. The coins predate that intervention by nearly a year.