The fraudulent fair-ground gamble which gave rise to the term 'play fast and loose' has a history in Europe going back probably to the 'Middle Ages'; certainly Shakespeare was familiar with it, writing in Antony and Cleopatra
'Like a right gipsy, hath, at fast and loose,
Beguiled me to the very heart of loss.'
Another name for the game was 'prick the garter' as a man's garter was often used to make the loop, and later a belt or strap, or even a piece of rope, was used and the game was called 'prick the loop'.
In Jamaica the game was known as 'stick-in-the-middle' and was widely played well into the 20th century; it was presumably brought here by English settlers from the 17th century, and reinforced by its popularity among British sailors, who played the con on a barrel top, or barrelhead, calling the gullible to 'put their money on the barrelhead'.
