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A poorly executed trust fall, i.e. you do not catch the person who is dropping back in to your arms.
Kendall was all set with this team building exercise until Barry was gabbing to Corbin and not paying attention, resulting in Kendall falling back to not get caught by Barry - trust fail.
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NOT TO BE CONFUSED WITH PENILE TRUST FALL!
This is the situation where there is a wooka wooka followed by a horrible cracking sound as the member strikes something it was not intended to.
Norbert: Wooka wooka babah….. (CRAAAACK!) Aaaaaaaaggghhhg!
Jimmy: Dangnoodle Nobert you’ve thrust into my diamond plated solar toaster and toothbrush combo set brah. Didja crackawillie?
Norbert: I must never trust thrust again my babah. I must get a fixawillie kit before I bleed out all of my life force.
Jimmy: Bet
See dat boy up in this bitch? He waz all like yo yo yo, but nah he ain’t got no play cuz he pulled a penile trust fail now he’s got a cracked willie.
When someone inherits a large sum of money as a minor but their Executor of Estate spends it all before they become of age. Oftentimes the Executor dies or disappears before they can be held accountable.
My grandpa secretly gambled my entire trust fund away but died before I found out. Oh well, guess I'm just a Failed Trust Fund Baby... feeling entitled but broke a.f.