Chicago:

American Slang

Definition

A metonym for mob-era, hardball tactics—ruthless, often violent or corrupt methods associated with the city’s gangster past.

Examples

"The negotiation turned Chicago fast—arm-twisting, payoffs, and veiled threats until the contract was signed."

"He warned the team that the rival firm plays Chicago, so keep your heads down and your paper trail clean."

"The campaign operatives went Chicago: ballot tricks, backroom muscle, and hush money to bury the scandal."