Green’s Dictionary of Slang

pigeon drop n.

also dropping the pigeon
[pigeon n.1 (2a)]

(US Und.) a confidence trick that involves dropping a wallet where a victim can find it or a scheme in which the con-man tells the victim that they have found a large sum of money and, if the victim will advance some money as a show of good faith, they can have a share in the ‘windfall’.

[US]Somerset Herald (PA) 3 Nov. 1/5: An elderly gentleman [...] was ‘done’ out of £260 [...] by two scamps, who ‘dropped the pigeon’ on him.
[US]J.H. Green Arts and Miseries of Gambling 217: There is another fraud practised on men who cannot be enticed into a game at cards [...] this trick is called dropping the pigeon.
[US](con. 1905–25) E.H. Sutherland Professional Thief (1956) 67: Among the short-con rackets, dropping the poke (also known as the pigeon-drop) is frequently used.
[US]Monteleone Criminal Sl. (rev. edn) 75: dropping the pigeon Bunco game; finding envelope or wallet containing large amount of money, dropped by a confederate, the victim being made to believe it was really found (Worked mostly by negroes).
[US]J. Wambaugh Blue Knight 187: He used to [...] work with a Gypsy dame on pigeon drops.
[US]E. Bunker Mr Blue 299: [He] was doing six months in the local jail for playing a con game called ‘the pigeon drop’.
[US]N.Y. Times Mag. 3 Jan. [Internet] Like the Spanish Prisoner, the Pigeon Drop, and other classic cons [...] it is subject to ‘Fields’ Law’ (You can’t cheat an honest man).

In compounds

pigeon dropper (n.)

(US Und.) a confidence trickster.

[US]Eve. Post (NY) 9 Apr. 2/6: I have just heard of a transaction, conducted by the managers of the Northerner [...] that would do honor to the [...] pigeon droppers of New York.
[US]Randolph Co. Jrnl 15 Apr. 2/5: Silent strikers, thimble-riggers, and political pigeon-droppers trooped forth.
[US]Nashville Union Amer. 17 Nov. 3/1: A Tennesseean Swindled [...] he took passage on one of the fiver boats at Cairo, and was followed by a pigeon-dropper.
Marshall Co. Repub. (Plymouth, IN) 29 Mar. 4/4: Suspected Felon Act [...] defines [...] 1. vagrancy [...] 4. a pigeon dropper.
Jasper Wkly Courier 3 June 1/2: Any person, who shall be found resorting to any trick or device to procure money [...] such as ‘Mexican puzzle’ [...] , ‘thimble and ballls,’ ‘pocket book dropping’ [...] shall be known as pigeon droppers.
[US]Bryan Dly Eagle (TX) 8 Oct. 2/6: [...] only to discover later that the $1000 roll was simply a wad of paper with a $10 bill wrapped around it. This [...] was known as ‘pigeon dropping’, amnd the operators as ‘pigeon droppers’.
[US]D. Burley Orig. Hbk of Harlem Jive 21: A Lane, thou art; Poppa Stoppa / Is only a pigeon dropper!
pigeon dropping (n.)

(US Und., also pigeon drop, pigeon game, dropping the pigeon) playing any form of confidence trick.

[US]N. Carolinian (Fayetteville, NC) 26 Oct. 1/6: It is surprising that [...] when the game of ‘drop pigeon’ has been published in all its modes, that victims to it are to be found.
[US]Dly Dispatch (Richmond, VA) 26 Apr. 1/3: A young man [...] was diddled out of $70 at St Louis on Thursday last, by the pigeon dropping game.
[US]Camden Confederate (SC) 20 Nov. 1/4: Vagabonds and swindlers are ready to fleece any one [...] at dropping the pigeon.
[US]Eve. Star (Wash., DC) 16 June 4/3: A colored man [...] joined them and introduced the ‘pigeon’ game by dropping a small bag with a three-cent piece in it.
[US]Oregon Republican (Dallas, OR) 16 Mar. 4/2: Unwholesome ornithogy — dropping the pigeon!
[US]Indianapolis Leader 11 June 4/4: Report of the arrests made [...] for the year ending June 1, 1881: [...] Passing Counterfeit money...3 [...] Pigeon dropping...2.
[US]Broad Ax (Salt lake City, UT) 23 Oct. 3/2: This [...] was known as ‘pigeon dropping’.
St. Louis Republican (MO) 7 Apr. 30/6: Two or more persons found acting together [...] for the purpose of pigeon dropping may be tried jointly.
[US]Aberdeen Wkly (MS) 27 Feb. 4/2: The two negroes who ‘dropped the pigeon’ on Berry were arrested.
[US]D. Burley Orig. Hbk of Harlem Jive 109: There was no chance of stopping those skulls who played at pigeon-dropping.