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The weirdest thing I have seen in a while.......

I like the idea that the guy in the OP's story lost a bet, but then I want to know more.

Or maybe he agreed to do this for a charity thing and got on the wrong side of a construction site.

Or maybe he's the foreman at that project, was all dressed for his other job or whatever he likes to do on his day off, then got a call to get to the site right away and didn't have time to change.

Or maybe... I could go on. There are any number of possibilities here, and I'm kind of bummed we'll never know.
 
It was a long time ago, but it seems to fit here.

I used to frequent Mid City Pawn and Loan in Omaha, Ne back in the '70s and early '80s. It was in a seedy part of town, but not too bad anyway. As I exited the store, I heard yelling. I turned to look, and there was Baron Von Rashke, aka The Claw from wrestling. He was yelling up at a window of a cheesy "hotel", where a rather ragged looking woman was hollering back at him. I later found out he lived in Omaha most of the time.

I only have a mental picture of it, but it's a darn funny picture.