Chicago bankroll noun a single large denomination note wrapped around small denomination notes, giving the impression of a great deal of money US,1966
— Edith A. Folb, runnin’downsomelines, p. 232, 1980
In the right pocket was something known in the trade as a “Chicago bankroll.” This consisted of one twenty wrapped around the outside of a roll of sixty ones and secured with a rubber band. — David McCumber, PlayingOfftheRail, p. 27, 1996