Green’s Dictionary of Slang

to cheat in cards or dice (occas. bowls), usu. in conspiracy with a confederate; thus booty fellow, one of a cheating team (also found in non-criminal senses). The result of such play is either to gang up on a third party, and share the resulting profits or ‘booty’, or deliberately to play to lose; also in fig. use; similarly used of horseracing (see cit. 1796) where a jockey deliberately loses; also used fig.

1555		Walker Manifest Detection (1850) 43: One man lost [...] an hundred pound land at shooting, by occasion that some that shot with him on his side, were booty fellows against him.
c.1561		Awdeley Fraternitye of Vacabondes in Viles & Furnivall (1907) 9: They thus ticklyng the young man in the eare, willeth him to make as much money as he can, and they wil make as much as they can, and consent as though they wil play booty against him.
1591		Greene Second Part of Conny Catching 8: The bowlers cast euer booty and doth win or loose as the bet of the gripe leadeth them.
1608		Dekker Belman of London F3: In this Law they which play booty are the Banckers.
1615		T. Overbury New and Choise Characters n.p.: [A Chamber-Mayde] If she catch a clap, she diuides it so equally betweene the Maister and the Seruingman, [...] only the knaue Sumner makes her bowle booty, & ouer-reach the Maister.
1676		Etherege Man of Mode III i: What think you of playing it on booty? [...] Pretend to be in love with one another.
c.1698		B.E. Dict. Canting Crew n.p.: he Bowls Booty, when great Odds are laid, and he goes Halves, his Cast is designed by Bad.
1725		New Canting Dict. n.p.: He bowls Booty, when great Odds being laid, and he goes halves, his Cast is design’d to be Bad.
1737, 1759, 1760, 1776		Bailey Universal Etym. Eng. Dict. [as cit. 1725].
1742		Fielding Joseph Andrews (1954) I 30: The best gamesters, before they laid their money, always inquired which horse little Joey was to ride; and the bets were rather proportioned by the rider than by the horse himself; especially after he had scornfully refused a considerable bribe to play booty on such an occasion.
1776		G. Colman Spleen I i: Jubilee started and stumbled; but, by-the-bye, I believe his rider played booty – Duenna won the stakes, and the knowing ones were all taken in.
1785, 1788, 1796		Grose Classical Dict. of the Vulgar Tongue n.p.: Booty, to play booty, cheating play, where the player purposely avoids winning.
1796		Sporting Mag. Aug. VIII 247/1: Every now and then [...] he gave a slight touch of the jockey, and played booty.
1797		Sporting Mag. Nov. XI 75/1: It was so evident that Darts fought booty, that none of the sportsmen would afterwards back him for a single halfpenny.
1799		Sporting Mag. Apr. XIV 40/1: I laid all the cash I had left, upon Mr. Cookson’s Diamond, who lost [...] I have a great notion the jockey rode booty.
1811		Morn. Post (London) 21 Sept. 3/3: Those who meant to bet upon Eclipse [...] openly condemned [its rider] for not playing booty .
1817		W. Scott Rob Roy (1883) 114: Were he caught playing booty, he would be disarmed, and probably dismounted.
1822		R. Nares Gloss. (1888) I 96: †booty. To play or bowl, or cry booty, appears to have meant to give people an advantage at first in order to draw them on to their loss.
1823		‘Jon Bee’ Dict. of the Turf, the Ring, the Chase, etc. 15: Booty, at play — when one’s partner [...] looses the game purposely, he is said to ‘play booty.’.
1824		Fife Herald 18 Mar. 4/1: He is like a man who attempts to finesse with a small card, when he has a sure winner in his hand [...] This tricky fantastic mode of prooceeding looks monstrously like playing booty with the enemy, and wishing to deceive his friends, the people.
1826		Pierce Egan’s Life in London 28 May 555/2: [of a recalcitrant perfoming dog] Carlo [...] seemed, according to the technical phrase, inclined to ‘play booty.’ After several other successive tricks, he would not jump; but, at last [...] made the desired leap, and repeated it at least a dozen times, as much to his own as to our satisfaction.
1834		(con. 1737–9) W.H. Ainsworth Rookwood (1857) 259: [of boxing] Each cove vos teazed with double duty, / To please his backers, yet play booty.
1838		Dickens Oliver Twist (1966) 107: Five of ’em strung up in a row, and none left to play booty, or turn white-livered!
1847		Fife Herald 10 June 2/4: [in fig. use] The political roguery of bothb factions has long been notorious [...] The patriots, as well as their press, are playing booty.
1850		Dublin Eve. Mail 2 Dec. 4/6: [in fig. sense] We have a strong opinion that Cardinal Wiseman and Lord John Russell are playing booty.
1858		Brighton Gaz. 3 June 7/4: [of cricket] When they speak of a man playing ‘booty’ at cricket nobody believes it.
1865		Dundee Courier 28 Nov. 2/1: If the news from Mexico be correct, the Federal officers at Brownsville [...] have compromised the Government by playing booty with a Republican officer.
1870		Leeds Times 7 May 6/5: He joined a gang of six that frequented rooms in Bow-street and told him their tricks. It was the old lay — sham watches and ‘playing booty’.
1880		Henley & Stevenson Deacon Brodie III tab.V iv: What made you cross the fight and play booty with your own man?
1888		Southern Reporter (Selkirk, Scotland) 28 June 2/6: The best gamesters, before they laid their money, always inquired which horse little Joey was to ride [...] especially after he had scornfully refused a considerable bribe to play booty. I presume ‘playing booty’ was the same things as ‘pulling’.