keep six


to hang back and watch out for somebody when they are going into a potentially dangerous situation. as in before a large illegal transaction, or while conducting a robbery.

has nothing to do with police being 5-0. actually derived from military communications. when an infantry squad is moving, one member may be -ssigned to “watch the squad’s 6”, meaning their 6 o’clock (behind them).
alright guys, there’s supposed to be no guns inside the pool hall, so you stay out here and keep six for me. if i you hear shots or i’m not out in 20 minutes, come in blasting.
to watch over; be a lookout for
“stay by the window and keep six for any cops.”
to be on the lookout
for example a robbery is being committed and one robber tells the other to go outside and keep six
to keep a look out for police, derived from cops being 5.0, so six means you’re one up on the cops.
i’ll park here and roll this up if you keep six!

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