whip saw, v. — Green’s Dictionary of Slang

whip saw v.

also whipsaw

[SE whip-saw, something that is disadvantageous in two ways; see Asbury, Sucker’s Progress (1938) 17: An extraordinary number of the terms, technical and otherwise, which were employed by Faro players in the palmy days of the game have passed into the language [...] and are commonly used by millions who never heard of Faro. Here are some of them: [...] Whipsawed — Losing two different bets on the same turn]

1. (US) to have at a complete disadvantage, to overcome completely; to benefit or win by manipulating a situation so that one’s rivals attack one another.

1884		Hartford (CT) Post Sept. n.p.: Had Braddock been half as prudent as he was brave, he could [...] have whipsawed the French and Indians in that campaign [DA].
1896		J.F. Lillard Poker Stories 119: The blacklegs showed no mercy. They did not let him win even a few dollars to encourage him, but either booked the cards every trip, or else whipsawed him until he was forced to drop.
1903		‘Hugh McHugh’ Out for the Coin 36: Plainly I was being whipsawed by circumstances.
1912		Ade Knocking the Neighbors 128: He double-crossed his Partners and whip-sawed his Customers and bluffed the Courts and bulled his way into the Strongholds of Finance.
1924		G. Henderson Keys to Crookdom 422: Whip-saw. Completely routed. Whip-sawed – beaten at every turn.
1935		A.J. Pollock Und. Speaks n.p.: Whip-saw, to lose both ways in gambling.
1948		Time 12 Jan. 40/1: They were just hoodwinked and whipsawed by Michigan’s slickers [DA].
1950		Goldin et al. DAUL 236/1: Whipsaw. To rob or swindle a difficult victim; to employ extreme resourcefulness in robbing such victim.
1982		G.V. Higgins Patriot Game (1985) 85: Isn’t anybody going to whipsaw old Seats into settin’ up a payoff.

2. to attack, to assault.

1902

Ade Girl Proposition 48: [They] were out to whip-saw the Cigarette, down the Cocktail and give a lasting Ki-Bosh to the Blue Chip and the Kitty.