two-time loser

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.

Word History and Origins

Origin of two-time loser¹

First recorded in 1930–35

Example Sentences

If he loses in 2024, he could run again in 2028; at that point, though, he would be a two-time loser.

From New York Times

A veteran print journalist, he was a two-time loser in cable news, having been fired from both CNN and MSNBC, leading to skepticism that he was the best choice to replace O’Reilly after he was ousted over sexual harassment allegations in 2017.

From Los Angeles Times

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

“Josh Mandel: Another failed career politician squish,” a new ad from a super PAC supporting Mr. Vance blared on Ohio television sets on Friday, calling Mr. Mandel, who is mounting his third Senate run, a “two-time loser” and “a moderate for the moderates.”

From New York Times