Wiktionary
n. Someone with bad luck or poor skills who consistently loses.
Usage examples of "three-time loser".
Bud picked a great first shot: a domestic squawk, the complainant a longtime punching bag, the arrestee a three-time loser.
Heart Attack was Voyteck Kirnipaski, three-time loser, also a known Katzenbach associate, his falls for extortion and grand larceny--specifically stock swindles.
Since he was a three-time loser serving a life sentence, if he took this job and it worked, the President of the United States would get him a pardon.
The next time he got caught he was a three-time loser and so they sent him up for life in the toughest prison in the state.
Guess what the guidelines are for a three-time loser going down on possession with intent?
You are sentenced to the Reformatory for conditioning against a repetition of this crime with the warning that next time you appear before me you will be a three-time loser and subject to complete character reformation.
They wouldn't let a three-time loser--a pushover for a fourth fall--stand in their way.
The hero of my story was your classic Poor Schmuck, a guy named Roger who had done jail time twice for counterfeiting money - one more bust would make him a three-time loser.
Makes me a three-time loser and that's twenty to forty at a minimum.
They finally busted him to make him a three-time loser and send him up for fifteen to thirty.