Taylor Dukes

The Taylor Street Dukes came to be out of the influence of the notorious Forty Two Gang.  The Forty Two Gang was founded by at least 1921, the same year notorious future Chicago Outfit member Sam Giancana joined the organization.  The groups started out as just really tough young kids on Taylor Street robbing and stealing to get by until they rose up to become Outfit…or at least some of them.  By the year 1925 the Forty Two Gang became well-known and documented which is why they are mistakenly said to have started in 1925.  By 1934 the Forty Two Gang became inactive on Taylor Street but their legacy remained.

Wise guys that were now part of the Chicago Outfit still lived and did business on Taylor Street through the 1940s and into the 1950s as they got to know many of the neighborhood kids and acquainted their own children with these same streets.

In the year 1954 a new wave of superhighway construction began in the Near West Side displacing many families from the community and causing many others to move out because of the undesirable changes in the landscape.  The value of the community decreased further after these changes making way for easier to afford housing which became attractive to many impoverished Puerto Rican and black families.  Puerto Rican and Mexican families especially settled along Taylor Street.  A cultural clash then ensued in 1954 as undocumented racial violence began.  In the midst of this the very young Italian youths felt the need to protect Taylor Street forming gangs.  The gang closest to the Outfit influence would became the Taylor Street Dukes.  These boys were only 12-13 years old when they started the Dukes and these boys had uncles and fathers who were notorious Outfit members; therefore, they began acting like gangsters too which made them became one step up above the other Taylor Street gangs.  As far as I know not a single Italian gang along Taylor Street ever gave the Dukes any trouble; therefore, the Dukes fought Hispanic and black gangs.

The original Dukes were Tony Senese who was 12 years old.  Don Longo who was also 12.  Pete Russo who was 13.  Bob Carrano who was 12 and Gary Calabrese who was 13 and the founder/leader.  These boys put the Dukes together and even recruited some Mexican members from their start as long as they were Americanized enough and tough enough.  The Dukes’ original turf was Taylor and Throop as they hung out with the Taylor Nobles.

The Dukes fought viciously with black gangs and caused the Egyptian Cobras to form in 1954 which would later become the notorious Mickey Cobras that still exist today.  The Dukes also fought the legendary Ambrose gang that also formed because of the Dukes and Ambrose still exists today as the Almighty Ambrose.  Dukes also fought the Imperials which was a Mexican and Puerto Rican gang that would later begin the legendary Latin Kings we know today.    The Imperials may have also started because of the Dukes as well.  It seems like any club that fought hard against the Dukes learned to become extra tuff and would later become giants.  The Dukes also fought the Harrison Gents in the later 50s and early 60s and the Gents still exist today as well.

By 1958 the organization was run by Gary Calabrese (Chicago Tribune Page 14 Oct 5, 1958) and it is likely that he may have been the one to pass everything down to the young Taylor Jousters in about 1959 or 1960. The Dukes became a little less active by 1961 then closed down in 1966 leaving everything to the Taylor Street Jousters.

In later years many of the older Italian Dukes became connected with the Chicago Outfit and some became wise guys.  The old Dukes started a group called the Compari Chiefs and they hung out at the old Distillery bar at Taylor and Loomis until well into the 1980s.

I believe Gary Calabrese became a Chicago police officer that policed the Taylor Street area.

Please send in 1950s and 1960s pics of Taylor Dukes.

Known sections of the Taylor Dukes from the past

Near West Side neighborhood Established 1954-1980s

Sections of Near West Side

Taylor Street from Throop to Loomis Established 1954-1980s