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the drunk dude who stumbles up to you at the tables(gambling) who tries to tell you what cards to keep,get rid of, etc..
check it out son, i know how to play, you can stop being the pitboss.
pitboss by fishegg July 12, 2004
Related Words

pitboss 2000 

The name for some queer bait 12 year old who tells people much older than himself to suck cock and eat shit.
"Hey look, its pitboss 2000, want to play a game with him?"
"No, that kid is a fucking queer."
pitboss 2000 by EpicDuckGuy May 5, 2015

Pit Boss 

A pit boss is the same as manager but in the gambling industry. He supervises the casino's pit like table games such as craps, roulette and poker.
He is in charge of all people working in a given pit including dealers or even maintenance personnel. He is responsible of the games there.
"Life is a gamble something like a pit boss, i keep it angry something like I'm pissed off" - Math Hoffa
Pit Boss by Mistah Atef November 10, 2010

pit boss 

a tv show on Animal Planet featuring a bunch of midgets trying to rescue pitbull dogs from abusive owners
Guy 1: You watchin' some kinda Jerry Springer special about midgets?

Guy 2: Nah, just a regular episode of Pit Boss.

Guy 1: Suit yourself. I'm gonna go masturbate to some Emma Watson fakes.

pit boss eyes 

Very observant and able to recognize particular individuals out of crowds or busy environments, especially when not expecting them to be there. Elements that would make a good pit boss at a casino.
My friend was constantly spotting famous people and old friends when we went out.

He seemed to take notice of everyone in the establishment.

He had those "pit boss eyes."
pit boss eyes by iGetNoRespect April 27, 2019

Pit Boss 

The Stranger with an assist. Have another person hit you in the cluster of nerves in your armpit with their thumb, causing your arm to go completely numb. Then, with your working arm, grab your dead arm and jerk yourself off.
After a long day, my buddy treated me to a pit boss.
Pit Boss by jmgateley February 29, 2020