sad sack
Synonym discussion
Sense: noun/1
Sad sack, loser, klutz, and failure all describe someone who does not succeed, but they differ in tone and scope. Sad sack is an informal American expression for a person whose awkwardness and lack of skill cause repeated failures — it carries a hint of pity rather than anger. Loser (stronger and more insulting) judges the person's overall worth, not just their competence. Klutz is limited to physical clumsiness and is often used playfully. Failure focuses on outcomes (the person does not achieve goals) and is more neutral and formal. Compare: 'Don't be such a sad sack — you'll get it right eventually' (encouragement mixed with sympathy) versus 'He's a total loser' (dismissive judgment).
Etymology
Sad sack first appeared in American English in the early 1940s. It may have been popularised by a cartoon character named 'The Sad Sack', a clumsy and unlucky army private created by cartoonist George Baker during World War II. Over time the term moved from military slang into general informal use to describe any person who is awkward, unlucky, and ineffective.
First known use
1942
1942, in the meaning defined above