Playboys, Ventures, Pulaski Park, Rice Boys
Playboys, Ventures, Pulaski Park, Rice Boys

Playboys, Ventures, Pulaski Park, Rice Boys

Founded Founded in 1958 by Guy and Teddy in or near Austin West Town: East Village West Town: Wicker Park
Founding story

Founded in Austin, East Village section of West Town, Wicker Park section of West Town

Formerly known as

Naturals 1958-1958; Sons of Satan Slaves 1960-1963; Coachman 1964-1969.

Affiliations United Five Organization — 1973 – 1982;
Colors Black and White
Primary ethnicities White
Symbols Playboy Bunny, Cane, Martini Glass, and Cross
Status Extinct

The first part of this story starts with the Playboys that started as a softball team called “The Naturals.”  The Naturals hung out in front of Anderson Elementary School located at 1148 N Honore St, Chicago, IL 60622 (now known as La Salle II Magnet School) in the Wicker Park neighborhood.  The boys also hung out in the back of the school in the Anderson Schoolyard.  The team also hung out front of Sammy’s Hotdogs that was also located at the same intersection of Division and Honore.  The team was formed in 1958 and were just a group of mostly Polish, Irish and German kids trying to play softball and were not started as a gang at first.  The kids played softball, Ring-Go-Levio and Hit-In-The Mouth.  The Naturals eventually used the team name as their identity and this converted them into a gang in 1958.  The Naturals wore black club sweaters with two dice showing a five and a two on the front.  The main alpha teammate was a kid named Guy who acted as the team leader.  The Naturals were mostly kids from lower income homes that were many times dirt poor.

Later in 1958, the Naturals began hanging out with another group of teens from nearby neighborhoods which created one larger group of teens that hung out together, some were members of the Naturals.  These teens started high school at Wells High School in 1958 (Augusta and Ashland in the East Village neighborhood 936 N Ashland Ave, Chicago, IL 60622).  At school they quickly got to see that the Italian gangs were running the high school, primarily the Dominos, Lazy Gents, C-Notes and Gaylords.  These Italian gangs bullied and harassed the Naturals and their friends because they would get attention from girls at school or would gather a following around them.  These Irish, Polish and German kids did not waste much time before they decided they needed to become one big gang to defend themselves against the Italians; they decided on the name “Playboys.”  The new sweaters were black with a playboy bunny as an emblem.  The female members were named “Playgirls.”

Guy and Teddy became the first leaders of the Playboys as the gang viciously battled against the Italian gangs that tried to prey on them.  Guy was in charge for a short time but perhaps didn’t lead the Playboys into the 1960s and Teddy took over full leadership.  Guy and Teddy were basically the founders of the Playboys and once they graduated high school in the early 1960s they faded out of the group.  Some of the original members got married after high school and left the gang life while other remained as older members.

In about 1962, the older Playboys began hanging out at a bar called Winchester Inn (1935 W. Thomas Street) that used to be located at the intersection of Thomas and Winchester in the East Village neighborhood.  These older members spent more time at the bar than at Division and Honore and as new members began joining the Playboys the gang split into Seniors and Junior members.  The Senior Playboys hung out at Winchester and Thomas at the bar while Division and Honore was rested away to the Junior Playboys who governed on their own.  The Junior Playboys even had their own female members they called “Playmates.”  Some of the original Playboys ended up in jail, dead or addicted to drugs in the early 60s but the rest created the new established territory at Winchester and Thomas which would become notorious for years to come.

The Junior Playboys hung out up and down Honore Street between Division and Ellen Street.  This is a very narrow one-way road and it made for an easy lookout for the Junior Playboys.  Members and others that lived in the area knew if you were to drive down this street you had to turn your bright headlights on as you drove down the street or else your car will get destroyed or you could get shot or beaten.  When there was a threat of invasion of rivals Playboys required you to flash your brights as you drive down.  These Junior Playboys were much more rough and violent than the original Playboys giving them a reputation for being a force to be reckoned with.

In 1960 or 1961 another gang called the “Sons of Satan Slaves” was just forming at Walsh Park (1722 N Ashland Ave, Chicago, IL 60622) which is located near Ashland and Cortland in the Wicker Park neighborhood.  The Satan’s Slaves also hung out on Marshfield Avenue which borders the park.  The Satan’s Slaves had much of the same story as the Playboys.  The Sons of Satan Slaves played softball and Ring-O-Levio in the neighborhood until Gaylords started coming around messing with them.  Eventually Lazy Gents, Dominos and C-Notes started messing with these kids too driving the to became a street gang.  The Sons of Satan Slaves were known for fighting with the Gaylords in the stairwells at Wells High School.  In about 1963 the Sons of Satan Slaves changed their name to the “Ventures” and they were a very tough gang that had a reputation for being very violent.  After becoming the Ventures their influence spread as many Polish, German and Irish youths wanted in on the Ventures and their turf expanded into the East Village neighborhood where much of the Junior Ventures landed.  The Ventures assembled a large chunk of turf in the area of Division Street on the north, Ashland Avenue on the east, Chicago Avenue on the south and Damen Avenue on the west.  The Ventures had much of the same story as the Playboys; they attended the same high school and had issues with the same Italian gangs and fought over girls.

The next part of the story in with “Pulaski Park.”  The Pulaski Park started in the early 1960s right at the park they were named after.  Pulaski Park is located at 1419 W Blackhawk St, Chicago, IL 60622 in the Wicker Park neighborhood.  The Pulaski Park gang became quite popular in this area and grew into pretty strong numbers mainly because this park was large in size and many people came to hang out in the park which exposed the Pulaski Park gang to many youth coming in and out of the park and soon neighborhood kids wanted to join the group of greasers hanging out in the park.  Right near this park was St. Stanislaus Kostka Church that had a school at Noble Street and Potomac Avenue.  The church is at Evergreen Avenue and Ada Street.  This parish is right next to the park and would host a carnival every year which invited many youths to Pulaski Park turf.  Rival gangs came to attend the carnival in search of girls and fun times and this made Pulaski Park angry and big gang brawls would ensue on these grounds.  Just like the Playboys and the Ventures Pulaski Park were Irish, Polish and German teens that fought with the same Italian gangs like Dominos, C-Notes, Gaylords and Lazy Gents.

The final part of the founding story was the creation of the “Coachmen” that formed in the year 1964 at the intersection of Wood Street and Thomas Street in the East Village neighborhood.  Once again this was a group of Irish, Polish and German youths that came together to fight against the Italian gangs like C-Notes, Gaylord, Dominos and Lazy gents.  The Coachman had issues with drug use as many members got into it pretty bad which caused them to already have issues with keeping their organization solid.  The Coachmen hung out with a nearby hang of Polish, Irish and German kids called “The 13th District” that had turf at Walton Street and Wood Street in the East Village neighborhood.  13th District got their unique name because the 13th District Chicago Police department is located right at that intersection.  Both gangs had a lot in common and even found more common ground in 1964 when Puerto Rican gangs started popping up in the area like Latin Kings, Warlords, Spanish Lords and various others.

Another piece to this story would be the founding of the Rice Boys, however, I don’t know their history at all except that they started in the Austin neighborhood at the intersection of Rice and Pine back when the neighborhood was mostly white.

In the year 1964, Playboys, Ventures, Pulaski Park, Coachmen and 13th District were now facing a new enemy, the Puerto Rican gangs.  Puerto Rican people began migrating the West Town in the late 1950s but tended to assimilate among the German, Irish, Polish, Italian and Ukrainian youths.  The only Puerto Rican gang around where the Imperials (later created the Latin Kings).  By the summer of 1964 there was a major boom in Puerto Rican gangs and much of West Town was not happy.

In the year 1964, the popularity of Puerto Rican gangs continued to swell and became threat to Playboys, Ventures and Pulaski Park, therefore these three gangs created a unity of their own called “Playboys, Ventures and Pulaski Park,” also know as P.V.Ps.

The best way to describe the P.V.P unity is a “all for one” mentality.  P.V.P was a strong unity and became legendary and still talked about heavily today.  Although Playboys, Ventures and Pulaski Park were still three different gangs that operated as one organization for the most part and even adopted the Playboy’s colors and symbols.

Gaylords, C-Notes and Lazy Gents territory was Chicago Avenue on the north, Ogden Avenue on the east, Grand Avenue on the south and Leavitt Street on the west.  P.V.P turf was Armitage Avenue on the north, the Kennedy Expressway on the east running down to Noble Street, Chicago Avenue on the south and Damen Avenue on the west.

After the P.V.P was put together, the Junior Playboys graduated into Senior Playboys while much of the original Senior Playboys had retired.  The new Senior Playboys were wilder than the originals and really made the Playboys more well known.

In the year 1965, the federal government started a program where they paid certain gang members to organize positive activities for the gang.  The Playboys were able to organize softball, flag football and field trips.  Each gang had junior and senior counselors.  The Senior counselors would resolve differences with rival gangs and take lingering issues to the boxing ring at the local Y.M.C.A where they could slug it out.  This program effectively cut back on street violence and gang wars but it ended less than a year later and the gangs just became worse afterward.

In the mid-1960s a new wave of young Playboys joined that were given the title of “Pee Wee Playboys” because they were very young and in Junior High.  This group proved to be some of the most ruthless members in all the P.V.Ps especially by the later part of the decade when they started high school and became Junior Playboys, while the Junior Playboys before them became Senior Playboys.

The late 1960s was a tough time as Senior members of P.V.P ended up being killed in the streets, ended up in prison, got drafted to fight in the Vietnam war (or volunteered) or started families and moved away.  Even Junior Playboys were succumbing to some of these circumstances and P.V.P numbers started to decline in between 1967 and 1969.

Neighborhoods like Wicker Park, Logan Square, East Village, East Humboldt Park and West Humboldt Park began to decline and became drug infested areas as poverty set in deep and more impoverished Puerto Ricans moved in.  Many white families found these communities to be undesirable and began moving along with the “white flight” wave leaving the white greaser gangs to decline in numbers, the P.V.P.s suffered from this quite a bit.  Now the white youths were becoming outnumbered and many were being bullied by Puerto Rican gangs as they tried to walk across the neighborhood, get on school buses or just go to the store.  White gangs were also heavily outnumbered as more Puerto Rican gangs were creating unities and teaming up against white gangs.  As more Puerto Rican people moved into these neighborhoods it also brought scores of prospects for Puerto Rican gangs to recruit from.  In 1969, the white gangs decided their wars against each other were not for the good of any of their organizations and a truce was made.  The war between the Italians against the Polish, Irish and German youths stopped as they now realized who the real common enemy was. P.V.Ps, Gaylords, Taylor Jousters, Lazy Gents, C-Notes, Chi-West all became allies in West Town.  Although this alliance was not as solid as P.V.P it was still a total ceasefire between their groups that would sometimes involve backing each other up in street fights.

The new alliance breathed life back into all the white gangs as recruitment sky rocketed right away in 1969.  The P.V.P.s had much success between the years of 1969 and 1970 as they expanded into the Austin neighborhood when Playboys and Ventures landed at Division and Waller and Galewood Park.  Playboys and Ventures also made their way into the Belmont-Cragin neighborhood at Wrightwood and Laramie and conquered Cragin Park.  The Playboys opened up in the suburb of Norridge at Montrose and Octavia in Octavia Park.  There was much demand for the need to be a part of white gangs in Austin and Belmont-Cragin as now Hispanics and blacks were moving into Austin.  In Austin the Playboys and Ventures found common ground with an Irish white gang that was already there called the “Rice Boys.”  The three gangs created a unity that was somewhat a spin off of P.V.P. that they called P.V.R. or “Playboys, Ventures and Rice Boys.”  The P.V.R.s in Austin battled viciously against Conservative Vice Lords, Cicero Vice Lords, Central Vice Lords and Ghetto Brothers Organization.  The fights were vicious in Austin as P.V.R.s were relentless against their enemies.

Part of the reason for the spread of Ventures and Playboys was the rise of the new Junior Playboys that were once the Pee Wee Playboys of the mid-60s.  These Junior Playboys were known for gangbanging in extreme fashions by shooting guns at their enemies instead of the traditional knives, bats, chains and car antennas.  The Junior Playboys also started hanging out at Winchester and Thomas in the early 1970s and by 1972 they had completely taken over that turf.  The first and second wave of Senior Playboys was more or less disappearing on the streets while these newer Playboys were becoming a big deal.  The Junior Playboys also had a new leader, high schooler Pete “Kong” Smolak was in charge of the Junior Playboys in the very early 1970s.

Pete Smolak was legend on the streets and was very well known among Pee Wee and Junior members of the P.V.P.  Tragedy fell upon the Playboys when Kong was killed by the Haddon Boys on July 2nd 1971.  During an altercation with the Haddon Boys Smolak was shot and instead of going to the hospital he went to gather his friends and plotted an attack against the Haddon Boys that involved ambushing them; however, the plan failed when they arrived and discovered the Haddon Boys were surprisingly well armed.  A major gun battle ensued between the two gangs and there really was no winner which was surprising because the Haddon Boys heavily outnumbered the Playboys. Despite the victory of holding their own Pete “Kong” Smolak was shot more times and died that day.

The Playboys suffered some decline after Smolak’s death but were still in a cease fire with other white gangs due to the new W.P.O. (White Power Organization) alliance that more officially kept the cease fire in tact and created a deeper unity between P.V.P.s, Gaylords, C-Notes, Taylor Jousters and Lazy Gents.  This closer unity brought about a brotherhood alliance that was as tight as P.V.P. called the “United Five Organization” or “U.F.O.”  This was put together in 1973 and it bounded Gaylord, C-Notes, Taylor Jousters, Chi-West and P.V.Ps/P.V.R.s into this brotherhood that effectively governed each organization to fight alongside each other in the streets against the Puerto Rican gangs.  The UFO also respected the WPO agreement but they mainly honored U.F.O before anything.  In the midst of the U.F.O alliance the P.V.P. became very acquainted with the Taylor Jousters and in areas where Playboys, Ventures and Jousters were hanging out a unity was created called “Playboys, Ventures and Jousters,” or P.V.J.  Pulaski Park was not part of this alliance for some reason.

In the mid-1970s the ruthless group of Junior Playboys became Senior Playboys and the P.V.P. as a whole was experiencing great success as their numbers grew but this would soon be short lived as many key Senior Playboys began to see jail time by 1975.  The WPO broke up after Gaylords went to war with Simon City Royals and Insane Popes.  Now this meant P.V.P, P.V.R. and P.V.J all had to war against them too.  This war mainly effected the Belmont-Cragin P.V.R.s.

In the late 1970s, Gaylords, Taylor Jouster and P.V.R. teamed up to fight against Simon City Royals and other Hispanic gangs for control of Hanson Park and Cragin Park.  The Jousters and Playboys especially fought the hardest and managed to take over these parks.  The Jousters took Hanson Park while the Playboys took over Cragin Park.  P.V.R. was developing a strong following in the late 70s as Hispanic migration dramatically increased in Belmont-Cragin and black migration turned Austin majority black.  This caused many more frustrated white youths to desire membership into P.V.R.  Austin especially was a neighborhood that needed membership and P.V.R. headquarters was established at Division and Waller, while a smaller headquarters was located in Octavia Park.  The new P.V.P. headquarters was set up at Austin Bowl at Central Avenue and Division in Austin.  The Playboys still used Winchester and Thomas as the headquarters for their own organization only.

In the early 1980s, P.V.P., P.V.R. and P.V.J. all went through a massive decline due to white flight and more incarcerations.  Austin had become over 90% black and this meant black gangs like the Vice Lords completely dominated the area.  Rice Boys and Playboys continued to make a last stand in the early 80s in this neighborhood but the first to fold were the Ventures as Crystal and Long fell.  Austin Bowl headquarters was shut down as Thomas and Pine, Crystal and Pine, Rice and Pine, Thomas and Menard and Chicago Avenue and Central Avenue all fell under Vice Lord control as white youths became a scarcity.  The headquarters for P.V.R. at Division and Waller closed down and there were no more headquarters left for the unity.

Wicker Park Ventures were also on a decline and eventually went extinct along with Pulaski Park in the early 80s.  Even at Winchester and Thomas Playboys were starting to decline in numbers.

In the year 1982, the U.F.O alliance was dissolved as Gaylords, Taylor Jousters, Freaks and Playboys all went to war with C-Notes.  This loss of the alliance hurt Playboy’s operations further as now they had a new war to engage in.

In the year 1984, the Playboys got a second wind as their recruitment drive dramatically picked up.  Wrightwood and Laramie now flourished as now there was a lot of Playboys hanging out in the park and viciously fighting Spanish Cobra invaders.  The Playboys successfully beat the Cobras back and the Cobras gave up trying to take over that park.

In the mid-80s the Playboys and Rice Boys fought their last stand in Austin but it was a losing battle against the many black gang members all around them.  These Playboys and Rice Boys were among the last white families to live in central Austin and they finally packed up and left the area.  The Playboys also had their last stand at Winchester and Thomas in the mid-80s and eventually closed that turf.

By the late 1980s, you could only find Playboys in one little section of the city at Wrightwood and Laramie in Cragin Park, even there they were starting to experience their first decline in numbers.  Octavia Park was closed down, hence, closing their only suburban turf.

In the early 1990s, Cragin Park came to an end as the last Playboys retired or moved away.  This brought an end to a major legacy that is not forgotten not only by those that had membership but also by those that fought against the P.V.P., P.V.R. and P.V.J. and perhaps suffered greatly going against them.

Please send in pictures of P.V.P, P.V.R. and P.V.J or any organization within this alliance.  Looking for old school pictures of members and/or graffiti from the past.


  1.  What exact year did the Pulaski Parkers start?
  2. Who was the founder of Pulaski Park and what happened to him?
  3. What year did Pulaski Park turf close?
  4. What exact year did the Pulaski Parkers go extinct?
  5. What exact year did the Rice Boys form?
  6. What was the founder of the Rice Boys and what happened to him?
  7. What years did each section open and close for Rice Boys turf?
  8. What exact year did Rice Boys go extinct?
  9. Who was the founder of the Ventures and what happened to him?
  10. What year did each Venture set up and close?
  11. What exact year did Ventures go extinct?
  12. What year did P.V.J break up? 1982?
  13. What was the time line of Playboy leaders before and after Kong?
  14. What exact year did the Playboys go extinct?