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

Better a private citizen than a two-time loser.

From Los Angeles Times

President Donald Trump might make another White House run in 2024, but if he does, he will take his place in American history as a two-time loser, House of Representatives Speaker Nancy Pelosi predicted on Thursday.

From Reuters

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

Under the leadership of Ward — a two-time loser of Republican Senate primaries, one against McCain — the party embraced election conspiracy theories: It called for the state legislature to “DE-CERTIFY the false results,” and when the state’s Republican Gov. Doug Ducey, an erstwhile Trump ally, defended the count, Ward tweeted that Ducey should “#sthu” — shut the hell up.

From Washington Post

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