Shakedown/ˈʃeɪkdaʊn/ Definition 1 of 4Pro Tip 1/3Negative Connotation Shakedown has a negative meaning, suggesting unethical or illegal pressure. Local businesses were tired of the mafia's shakedown demands. Pro Tip 2/3Implies Coercion Use 'shakedown' when someone is coerced into giving money, often protecting from harm. The nightclub owner paid the gang to avoid a shakedown. Pro Tip 3/3Often Illegal Shakedown typically refers to activities that are illegal or borderline legal. He got arrested for his role in the shakedown of tourists.