The sentience of “I can’t win from losing” is a statement of when things go repeatedly wrong in an individuals life (losing), and even when things continuously goes wrong they can never catch a break.
Friend #1: Wow, So you lost your job and your wife?
Friend #2: Yea, I was fired and Susan left me…
Friend #3: Dang you can’t win from losing.
Friend #2: Yea, I was fired and Susan left me…
Friend #3: Dang you can’t win from losing.
by Zebracakesaresatire May 13, 2023

by Mk.Immaculate January 17, 2021

by alex_g87 March 17, 2011

A character in a story, TV show, movie, etc. that only grows stronger as circumstances get harder so there is never any real chance of losing
by Mushroomtattoo May 29, 2018

If you buy five of the scratch-off tickets that say, "Win up to five times", it very likely will refer to how many times the STATE will win, since you were idiotic enough to spend the money on those five tickets and probably not win anything yourself.
by QuacksO September 12, 2019

A state of being achieved only after snorting inhuman amounts of cocaine (also known as "banging seven gram rocks"), starring in a gut-churningly horrible television show for several years, and then completely losing your mind because it "fires in a way that is not from this particular terrestrial realm".
Side effects include erratic behaviour and having tiger's blood.
Side effects include erratic behaviour and having tiger's blood.
Interviewer: Some are saying that you're bi-polar.
Bi-Winner: Wow, what does that mean?
(awkward pause)
Interviewer: I guess that you're on two ends of the spectrum.
Bi-Winner: Wow, and then what? What's the cure? Medicine? Make me like them? Not gonna happen. I'm bi-winning; I win here, I win there, now what?
Bi-Winner: Wow, what does that mean?
(awkward pause)
Interviewer: I guess that you're on two ends of the spectrum.
Bi-Winner: Wow, and then what? What's the cure? Medicine? Make me like them? Not gonna happen. I'm bi-winning; I win here, I win there, now what?
by MartinSheen March 22, 2011

Paraphrasing from the slogan “must-win-battles” it can be applied to a drinking competition or to a good night out with blokes.
Acronyms: MWB
Acronyms: MWB
T: Hi bro, how was that mission to the Oktober Fest?
M: I tell you what, it has been like a must-win-bottle, I have never been so drunk!
M: I tell you what, it has been like a must-win-bottle, I have never been so drunk!
by milfonian July 24, 2012
