In the fall of 1989, a youth program was developed to provide kids an outlet and opportunity to play the game of basketball in Pewaukee. The early days began on the grounds of the 'old' middle school location, now home of the Pewaukee Library.  The pioneers of the program were Steve Schill and John Maltsch.  

Steve, a Pewaukee alum and JV boys coach, had the desire to begin a basketball program to develop players for the high school program. John, another PHS grad and former Athletic Director at PHS, was approached by the park and rec department to organize a basketball program. With the assistance of Dave Schill, the three men embarked on building the early foundation of the basketball program in Pewaukee.

The youth program began with nearly 65 girls and boys 5th through 8th grade. As the program grew in popularity, the level of participation continued to grow to over 150 kids with games being played in the hollow gym of the vacated middle school. 

A few years after the inception of the program, Steve's career took him to Kansas City and John became the AD at Waukesha South. Dave was provided the reigns of the program. 

Participation levels continued to grow as the program added 3rd and 4th graders. Four divisions were created from 3rd to 5th grade and 6th to 8th grade for boys and girls. Kids were instructed on the fundamentals of the game and instructed on the rules of the game. Teams were formed, t-shirts were ordered and the making of a strong youth program was underway.

The youth basketball program, known as the Jr. Pirate program today, grew to over 400-participants from those early days, however something more was required to change the history of basketball in Pewaukee.  

Dave took a group of 5th grade boys to a tournament at UW-Waukesha in the winter of 1994. The result of game one was a 44-5 thumping. There was an apparent need for a more competitive based program. In the fall of 1995, the Club Program was developed to create and build a new tradition of success for Pewaukee basketball.