Green’s Dictionary of Slang

1. a dilemma, a difficult situation, trouble.

1887		G. Devol Forty Years a Gambler 117: We devoted ourselves to studying how to get out of the ‘jack-pot’ we had got into, without losing our stake.
1905		A. Binstead Mop Fair 107: Do they take this for a jackpot?
1914		Jackson & Hellyer Vocab. Criminal Sl. 48: jackpot [...] a dilemma; a difficult strait; a retribution; trouble; an arrest.
1922		P.A. Rollins Cowboy 79: Poker’s ‘jack-pot’ signified either a general smash-up or else a perplexing situation.
1943		R.L. Bellem ‘Dead Man’s Guilt’ Dan Turner – Hollywood Detective May 🌐 Some jane was in a jackpot; and I’m a sucker for damsels in distress.
1954		(con. 1938) C. Chessman Cell 2455 103: What’ll probably happen is that I’ll do all right for myself and you’ll wind up in a jackpot.
1962		F. Norman Guntz 111: My mate the major was in a right Jack-Pot.
1977		E. Bunker Animal Factory 121: I was worried that you’d get him in some kind of jackpot . . . jeopardize him.
1981		H. Gould Fort Apache, The Bronx 38: I meet a guy who takes a lot of chances, always wantin’ to fight, and gettin’ in jackpots all the time.
1997		Simon & Burns Corner (1998) 186: Ronnie was good at spotting a jackpot.
2011		J.J. DeCeglie Drawing Dead [ebook] Remember that jackpot I knew was waiting round the corner, well here I was living it, and it was just as much a motherfucker as I had expected.
2017		D. Winslow The Force [ebook] If they know about Piccone, do they know about the Fat Teddy rip, too? That puts Russo and Monty in the jackpot with you.
2023		(con. 1962) J. Ellroy Enchanters 176: Monroe knew Shelley Mandel in ’48. 1948 triggered jackpots.

2. an arrest.

1914		see sense 1.
1936		(ref. to 1920s) L. Duncan Over the Wall 32: Well, if you ever get yourself in a jackpot, you’ll have a reproduction of your mug, but you won’t send any copies back to the old home town.
1952		(con. 1948) G. Mandel Flee the Angry Strangers 19: ‘They’ll be looking for you.’ ‘They’ll have to look hard [...] No more jackpots.’.
2008		R. Price Lush Life 236: Possession is nine-tenths of the jackpot .