Definitions

1. noun

A person, especially a man, who is considered to be clever, resourceful, and skilled at achieving his goals, often by means that are unorthodox or unethical.

“The wiseguy tried to talk his way out of the ticket.”

2. noun

A member of the Mafia or a similar organization, especially one who is involved in organized crime.

“The FBI was investigating the wiseguy for his alleged ties to the mob.”

3. adjective

Clever, resourceful, or skilled, but often in an unorthodox or questionable way.

“The wiseguy’s plan to fix the game was eventually exposed.”