Green’s Dictionary of Slang

two-time loser n.

[loser n. (2)]

1. (US Und., also two-timer) a person who already has two convictions and so risks a higher sentence the third time (cf. three-time loser under three adj.).

[US]Amer. Mag. 77 June 31–5: Five years ago I was editor and manager of a metropolitan daily newspaper. To-day I am a convict serving my second penitentiary sentence – a ‘two-time loser’ in the language of the underworld.
[US]V.W. Saul ‘Vocab. of Bums’ in AS IV:5 345: Two time loser — One who has been twice in the penitentiary.
[US]R. Chandler ‘Blackmailers Don’t Shoot’ in Red Wind (1946) 119: Your Luger got Mike Corliss, a two-time loser.
[US]D. Lamson We Who Are About to Die 126: Qwong was a bad boy. Qwong was a two-time loser.
[US]Mencken Amer. Lang. (4th edn) 580: In virtually all American prisons [...] a recidivist is a two-time loser (or three-time or n-time, as the case may be).
L.J. Valentine Night Stick 240: Peter Colavecchio was holed up with ‘graduates’ of various penal institutions. There was Louis Scotti, Dave Bloom, and Tony Cutro, all of them two-time losers.
[US]Lait & Mortimer USA Confidential 271: His brother is a two-time murder loser.
[US](con. 1948) C. Chessman Cell 2455 293: Would a two-time loser who intimately knew the ins and outs of crime approach a car unmasked and proceed to commit penny ante crimes punishable by death.
[US]‘Red’ Rudensky Gonif 98: Both are two-time losers. They’ll be careful.
[US]S. Ace Stand On It (1979) 94: I’m what they call a two-timer. That is: I get caught out there one more time with a load of stuff and they haul my ass away to jail for good. I done lost two times now. The third one is it.
[UK]J. Morton Lowspeak.
[US]J. Stahl Plainclothes Naked (2002) 2: Ask him why, if the morning went really south, he had decided visit his mom with a two-time loser who’d showed up on America’s Most Wanted.

2. (US) a person who has been divorced twice.

[US](con. 1949) J.G. Dunne True Confessions (1979) 195: For a two-time loser [...] you give out an awful lot of advice about other people’s marriages.