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Underboss or Vice-Leader or Second In Command is the second highest rank in a gang just right behind the leader. The Underboss can make decisions but has to inform the boss to gain his/her approval. The Underboss is often related to the Boss. Carl Johnson was a Vice-Leader of the Grove Street Families while his brother Sean Johnson is the leader. During a gang war an Underboss is mostly targeted by other rival gangs and so is the Don and his Consigliere. The reason they are mostly targeted is because they are the leading members of a gang will prevent the gang of getting a new leader due to the Underboss being next in line to being the Leader.
- Carl Johnson - Grove Street Families (1992 - ?)
- Huang Lee - Algonquin Triads (2009 - ?)
- Lance Vance - Vercetti Family (1986), Vance Crime Family (1984 - 1986)
- Patrick McReary - Irish Mob (? - 2008)
- Gordon Sargent - Irish Mob (2008 - ?)
- Little Jacob - Yardies
- Dimitri Rascalov - Faustin Family (? - 2008)
- Wu Zi Mu - San Fierro Triads
- Salvatore Bottino - Gambetti Family
- Roy Zito - Gambetti Family (? - 2008)
- Harry Hall - Messina Family
- Mark Lupisella - Lupisella Family
- Charles Matteo - Ancelotti Family (? - 2008)
- Johnny Sindacco - Sindacco Family (? - 1992)
- Gonzalez - Cortez Crew (? - 1986)
- T-Bone Mendez - Loco Syndicate (? - 1992)
- Unnamed Cartel Boss - Colombian Cartel (? - 2000)
- Ron Jakowski - Trevor Philips Enterprises