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Always thought it was a sarcastic saying... So saying it backwards is warranted..

Would anyone rather their guy win the job, but we lose lots of games? or Someone else wins and we win all our games?

English teachers and grammarians will say that "could care less" is wrong because it should mean the opposite of "couldn't care less." Logically, if you could care less, it means you do care some. But in informal speech people often use "could care less" to mean they don't care at all but good...

Could care less... The best one... whoever wins games