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1.
It's a term used about how you hold your money. Some think that its all singles with a twenty on the outside. But, original it's was used for when you are in public. People can't see if your ballin, so you put the big bills in the middle and you work outward.
That kid is smart carrying that Chicago Bank Roll.
by junior burnett March 08, 2005
 
2.
A roll of money, consisting entirly of singles, with the exception of a twenty wrapped around the outside.
I thought he gave me the whole amount, turns out it was a chicago bank roll.
by M R January 17, 2004