(To). To cheat, to gull one of his money by almost self-evident hoaxes. Pigeons are very easily gulled, caught by snares, or scared by malkins. One easily gulled is called a pigeon. The French pigeon means a dupe.
“Je me deffleroy tantost que tu serois un de ceux qui ne se laissent si facilement pigeonner a tellesgens” —Les Dialogues de Jacques Tahureau, (1585).
Flying the pigeons. Stealing coals from a cart or sack between the coal-dealer's yard and the house of the customer.
Flying the blue pigeon. Stealing the lead from off the roofs of churches or buildings of any kind. To pigeon a person is to cheat him clandestinely. A gullible person is called a pigeon, and in the sporting world sharps and flats are called “rooks and pigeons.” The brigands of Spain used to be called palomos (pigeons); and in French argot a dupe is called pechon, or peschon de ruby; where pechon or peschon is the Italian piccione (a pigeon), and de ruby is a pun on dérobé, bamboozled.
To pluck a pigeon. To cheat a gullible person of his money. To fleece a green-horn. (See Greenhorn.)
“ `Here comes a nice pigeon to pluck,' said one of the thieves.” —C. Reade.
Source: Dictionary of Phrase and Fable, E. Cobham Brewer, 1894