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Sack is an antiquated wine term referring to white fortified wine imported from mainland Spain or the Canary Islands. There was sack of different origins such as: 1  Canary sack from the Canary Islands,
Slang sense of inferior, pathetic is from 1899; sad sack is 1920s, popularized by World War II armed forces (specifically by cartoon character invented by Sgt. George Baker, 1942, and published in U.S. Armed Forces magazine Yank), probably a euphemistic shortening of common military slang phrase sad sack of shit.