a two-time loser Definition

loser
noun

1. Someone or something that is defeated.

Example: The horse always looked a loser
Thesaurus: failure, flop, sufferer, underdog.
2. colloq
Someone who is habitually unsuccessful.

Idiom: a bad loser (a poor loser, a good loser)

Someone who loses in bad, poor or good spirit.

Idiom: a two-time loser (a three-time loser, a big-time etc loser)

Someone who has been to prison two, three, many etc times.