Around the same time that the baseball team was formed and started selling drugs, a gang called the Latin Kings began expanding into more and more Southside territory. Eventually they moved into Little Village. The Latin Kings started claiming the area as their own and began selling drugs in the Two Sixers’ neighborhood. The Latin Kings started harassing the baseball team whenever the Two Sixers were found selling in Little Village and tensions rose between the gang and the baseball team.
At this time, the Latin Kings were not the only gang giving the Two Sixers trouble but they were the main problem for the team. The tension between the two gangs eventually led to fights and it was this that forced the Two Sixers to become a gang themselves and to start to recruit to boost their numbers.
The area around Sawyer, 24th-23rd street and territory on 26th street all became the Two Six’s first hood. It was then that they became known as the Two Six Boys. As many young people in the Little Village community were tired of the Latin Kings and other gangs, the Two Six Boys found it easy to recruit. During the 1960s, as well as fighting the LKs, the gang also fought Ambrose, Satan Disciples, Kool Gang, and Villa Lobos. Their fights gained them a greater and greater reputation and so by the early 1970s the Two Six's were recruiting in ever greater numbers. In the late 1970s, and under the influence of their new leader David Ayala, the Two Six’s expanded into neighborhoods such as Brighton Park, Pilsen, and Back of the Yards.
In 1975 the Two Six's joined forces with two other gangs: the Folk Nation and the F.L.D.N (Familia Latino Disciples Nation). The F.L.D.N. was itself an amalgamation of six Latino Chicago street gangs including: Spanish Cobras, Satan Disciples, Imperial Gangsters, Latin Eagles, the Two Six's, and the Latin Disciples. This made F.L.D.N the only unified Latino Folk gang for the whole city. The United Latino Organization (ULO) only consisted of the Spanish Cobras, Imperial Gangsters, Latin Eagles, and the Latin Disciples.
The unified Two Six brought them into contact with their old enemies Ambrose and SD. This led to Two Six and Ambrose becoming first cousins and then getting involved with GDs (BGD at the time) and SDs. At this time, the Two Six's became known as Two Six Disciples and they started using the tag TSD in their graffiti. However, the TSD tag didn’t last long as they soon changed their name to Gangster Two Six in order to honor the GDs.
By the early 1980s, the Two Six's had a large presence in Chicago, covering an area that included: Central Park to Kostner/24th to 32nd, 4100 block of 25th street, a game room at 4012 W. 28th street and 2700 block of South Kedvale. They even had a presence on Ridgeway. Their members attended a number of schools, including Eli Whitney Grade School, Corkery Grade School, Curie H.S., Gary Grade School, and Farragut H.S.
On October 16 1981, the 18-year-old Two Six’s gang leader David Ayala killed two Latin King gang members. In January 1983, he was sentenced to Life in prison. He is still behind bars and currently resides at the Tamms correctional facility.
Around 1988-1989 the SDs went to war with the Two Six's because an SD murdered a Darkside Two Six on the corner of 26th and Pulaski. Even though this war severely fractured the F.L.D.N., it had to continue. Despite the fact that the war started during a time when there was less tolerance for gangs and gang warfare, and when there was a move to unify neighborhoods, it didn’t stop the fighting.
Throughout the 1980s and 1990s the reach and power of the Two Six's continued to grow so rapidly that they were accredited with being the fastest growing gang in Chicago history. In the early 1990s the Two Six's began to spread their operations into Cicero, IL, where they soon became a major force. In the 1990s the two Six's have been in conflict with fellow Folk Nation gangs. They have had on-and-off fights with Ambrose and more intense conflicts with the Two Two Boys (this was started when the Two Six's crashed a party and shot up both Ambrose and the Two Two Boys).
In the 1990s, the SD and Two Six war became increasingly bloody due to the fact that the Folk Nation bylaws were not as heavily enforced on the streets after 1991. In 1996 the Two Six's went to war with the Gangsters Disciples.
The Two Six's are a very violent street gang. The gang members are well known for just shooting their enemies, a trait they have been known for this since the 1960s.
- Dark Side Two Six , 24th to 26th , Kostner to Pulaski
- 24th & Karlov (Two Four Karlov)
- 25th & Keeler (Two Five Keeler)
- K-Town : 26th to 32nd , Kostner to Pulaski
- 27th & Keeler
- 27th & Tripp
- 28th & Kolin "Ghetto Side"
- 28th & Komensky
- 30th & Kedvale "No Love Side"
- 32nd & Karlov
- Chi-Town : 23rd to 33rd , Pulaski to Hamlin
- 24th & Avers
- 26th & Avers
- 27th & Avers
- 30th & Harding (Harding Two Six)
- 30th & Hamlin
- 30th & Lawndale
- 30th & Pulaski
- 31st & Avers
- Cicero,IL : (Parkholme Two Six)
- 16th to Cermak Rd*, Laramie to 51st ave.
- 18th & 51st
- 21st & 50th ct.
- Cermak Rd*to 26th , 51st ave*to Cicero Ave.
- 24th & 49th ave*(Two Fourz)
- 38th & Albany "Terror Town" (Albany Two Six)
- 38th & Francisco
- 46th & Mozart
- 47th & Damen (Damen Two Six)
- 47th & Albany- "No Love Ville"
- 63rd & Central (Central Two Six)
- 63rd & Knox
- 62nd to 67th (Marquette) , Pulaski to Kedzie
- 63rd & Hamlin
- 63rd & Homan "Homicide Town"
- 64th & Spaulding
- 67th & Kedzie
- 68th & Hamlin
- 69th & Lawndale
- 79th & Lawndale
- 159th & Wentworth , Calumet City,IL
- Hanover Park,IL
- Joliet,IL "East Side J-Town" , Marion & Hunter
- Rock Island,IL
- Villa Park,IL
- East Chicago,In
- El Paso,Tx
- San Antonio,Tx
- 24th & Millard
- 24th & Lawndale
- 24th & Sawyer
- 26th & Pulaski
- 26th & St.Louis
- 28th & Kostner
- 30th & Avers
- 46th & Albany
- 46th & Whipple
- 46th & Troy
- 59th & Rockwell
- 79th & Lavergne : Burbank,IL
- Addison & Major
- Sunnyside & Bernard
- Sunnyside & St.Louis
- Hoffman Estates,IL