Who Was Richard "Pee Wee" Kirkland? A Legend In Two Games

When you talk about legends who shaped both the streets and the hardwood, few names echo louder than Richard "Pee Wee" Kirkland. Born on May 6, 1945, in Manhattan, New York, Kirkland’s story is one of brilliance, contradictions, and lasting influence — a man who carved out his own lane in basketball and beyond.

Kirkland made his mark early as a standout varsity guard at Charles Evans Hughes High School in Manhattan, where he earned All-City honors. His scoring ability and raw talent caught the attention of scouts, landing him a scholarship to Kittrell College in North Carolina. There, he dominated the court, averaging an astonishing 41 points per game.

Later, he transferred to Norfolk State University, joining forces with future NBA star Bob Dandridge. Together, they led the Spartans to the CIAA title in 1968 with a 25–2 record, a historic run that cemented Kirkland’s reputation as one of the most electrifying players in the country.

In 1969, the Chicago Bulls drafted him in the 13th round. But unlike most young athletes chasing an NBA dream, Kirkland famously declined. The reason? His ventures outside of basketball — particularly in the drug trade — were far more lucrative at the time.

Pee Wee’s legend wasn’t confined to the basketball court. By the late 1960s and 1970s, he was a well-known figure in New York’s underworld, running high-stakes operations that made him more money than the NBA could offer. His life reflected the difficult crossroads many young men from urban America faced — choosing between a legitimate career with modest pay or the streets, which offered fast money and notoriety but carried deadly risks.

Despite his street reputation, Kirkland reinvented himself as a mentor and educator. In the 1990s, he launched “School of Skillz”, a basketball and life skills program co-sponsored by Nike. Starting in Harlem, the camps quickly expanded nationwide, using basketball as a tool to reach at-risk youth.

Kirkland’s unique credibility — built on both his basketball genius and his gangster past — allowed him to connect with young people who might otherwise tune out traditional voices of authority. His message: greatness doesn’t come from the streets, but from discipline, education, and self-belief.

He later went on to coach and win championships at The Dwight School, a prestigious private school in New York City, further showcasing his ability to navigate both worlds. Along the way, he earned a master’s degree in human services from Lincoln University, solidifying his commitment to education and community work.

Kirkland’s story transcends basketball. He appeared as Georgetown recruiter Phil Redd in the 1994 basketball classic Above the Rim, and was even referenced by hip-hop duo Clipse in their iconic single Grindin’. His name remains etched in both basketball folklore and hip-hop culture, symbols of authenticity and influence.

Pee Wee Kirkland remains a paradox — a man who walked away from the NBA for the streets, but later turned that same notoriety into a tool for uplifting others. A legend in both basketball and street culture, Kirkland’s life serves as both a cautionary tale and an inspiring story of redemption.

He is living proof that while choices can shape destinies, reinvention and impact are always possible.