two-time loser

American  

noun

Slang.

1. a person who has been sentenced to prison twice, especially for a major crime in a state where a third sentence is mandatory life imprisonment.

2. a person who has failed at the same endeavor twice.

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Etymology

Origin of two-time loser

First recorded in 1930–35

Example Sentences

Padma says "sorry your return was this short," and Dale calls himself a two-time loser.

From Salon

Being tarnished as a two-time loser would be too devastating to his psyche to risk it.

From Slate

Keiko Fujimori, a two-time loser in presidential races and the daughter of Alberto Fujimori, the former president serving a 25-year prison sentence for crimes against humanity, stands accused of taking bribes and laundering money.

From Los Angeles Times

Fish and Wildlife Service can do is assure the public that a two-time loser won’t be breaking anymore wildlife laws on the taxpayer’s dime.

From Washington Times

Then there's his advanced age, propensity for verbal stumbles, allegations of inappropriate physical contact and status as a two-time loser in past White House bids.

From BBC