|Founded||Founded in 1988 in or near Gage Park|
|Colors||Blue and Yellow|
|Primary ethnicities||Latino (Mexican)|
The Insane Guess Boys were formed in 1988 at the intersection of 57th and Artesian in the Gage Park neighborhood. I do not know who was the founder but original members included Plumber, Jerry and Huggies. The Guess Boys formed in wake of an increase of gang activity in the Gage Park and Marquette Park area especially when the Crown Town Latin Kings were growing and the creation of the Marquette Park Krazy Get Down Boys.
The Guess Boys were more of a party crew but they were so down they behaved like a gang and had great access to firearms supplies. In the year 1991 the Gangster Disciples and Black P Stones began moving into Gage Park and Marquette Park. By this time the Guess Boys controlled 55th down to 58th and Artesian as they were pushing to take from Talman to Western as they were morphing into a larger gang in the area. These were perhaps their best years of activity. When the Black P Stones arrived it spelled trouble for the Guess Boys as the Stones violently fought their way into Guess Boys territory to take 56th and Campbell this brought a war with the Stones. The Guess Boys then established an alliance with the Gangster Disciples and began dealing in firearms with the GDs, this is also when the Guess Boys would join the Folk alliance.
In the year 1993, the Guess Boys began to get into altercations with the Party People especially since the Party People were on a recruitment drive that year, this sparked a war with the Party People which would become bloody and costly for both sides. A Guess boy then shot and killed a Party People in the head the the Party People hit back by killing a Guess Boy by crushing him between a car and a brick wall on 59th between Campbell and Artesian. A little later Party People stabbed a Guess Boy at 56th and Western. These conflicts alongside other issues with other rivals and key incarcerations of high ranking Guess Boys caused the group to become inactive as their territory fell to Vice Lords and Party People.
In the year 1999, original members Plumber and Alfie reorganized the Guess Boys at 59th and Talman. Right away the Guess Boys got into hard with the Party People. This brought about a series of two major shootings were multiple Guess Boys were shot by Party People. After this costly conflict most of the Guess Boys flipped to Maniac Latin Disciples from the neighborhood.
In the 2000s decade some former Guess Boys would still hang out with the Gangster Disciples and engage in gang banging until the late 2000s but there was never a group reformed during that time period.