The South Side Gang was a mobster gang that controlled the South side of Chicago, Illinois. Led by Big Louis Costillo, with his right hand man Johnny Lovo, the gang profited really good off of Prohibition during the early 1920's. They had a rivalry with the Irish gang that controlled the North Side of Chicago, though things remained calm as long as they stayed in the South Side.
The Gang went through a split in factions during a power struggle between Costillo and Lovo. One day while at his club, Costillo was killed by one of his enforcers Tony Camonte, who was sent by Lovo. Lovo took over as boss, with camonte as his right hand man. Camonte and his men started shaking down other speakeasies into buying from them, including a speakeasy on the North side, run by Irish boss O'Hara, thus angering Johnny. As payback, The northsiders killed one of johnny's men, and threw his dead body outside of their social club with a note warning them to stay out of the north side.
Tony had his enforcer Guino Rinaldo kill O'Hara at his flower shop. O'Hara's successor Tom Gaffney went to war with the Southsiders, however tony and his men fought back hard against them. Killing a large number of gaffney's men, and expanding their rackets into the North Side. Gaffney and his men were later tracked down and killed by Tony at a bowling alley.
Tensions then started growing between Tony and Johnny, partly because of the drama with the Northsiders which tony started, but mostly because of Tony falling in love with Johnny's girlfriend Poppy. He then sent a hit group to kill tony, though he survived and bribed one of his men to tell Johnny that the hit was a success. Tony and Guino then went to the social club and killed Johnny, Thus taking over the gang. However, the war with the Northsiders increased the heat from the police.
After a misunderstanding causes tony to kill guino, the police raid tony's apartment building, and get into a shootout with tony and his sister francesca. after she is accidently killed by a stray bullet, tony attempted to flee, but was killed by the police, thus leaving the gang leaderless.
Leadership[]
Underlings[]
- Guino Rinaldo †
- Angelo †
- Tony
- Pietro
- Joe
- Keets †
- Berdini †
- Ziegler †
- Meehan †
- 4 Unnamed Hitmen †
- 40-60 Members
Associates[]
- Epstein
- 2 Unnamed Speakeasy Owners
Fronts and Properties[]
- Tony’s Apartment Building
- The First Ward Social Club
- Columbia Cafe
- South Side Speakeasies
Trivia[]
- they are heavily inspired by the real life South Side gang, more famously known as the Chicago Outfit. Led by Al “Scarface” Capone, whom Tony Camonte is largely based off of.