“Built Different: Roosevelt Cunningham III and the Mindset Behind the Grind"

By: Kavon Baptiste 

Roosevelt Cunningham III’s basketball journey is built on resilience, adaptability, and an unshakable competitive mindset. A homeschooled senior basketball player, Cunningham has taken a nontraditional path in pursuit of his goals, one that has shaped both his game and his character. What separates him is not just his size or skill, but the mentality he brings every time he steps on the court.

Cunningham’s love for basketball began in middle school after he stepped away from football, where he once played Offensive Guard and Defensive Tackle. Searching for something new, he picked up a basketball and never put it down. What started as a way to stay active quickly became a passion and a purpose. Since then, basketball has been his primary focus, driving him to refine his skills and continually improve.

Standing around 6’4”–6’5”, Cunningham plays primarily as a forward, often lining up at the 4 or 5 position, while showcasing the skill set of a modern point forward. He prides himself on his versatility, rebounding, shooting, passing, and making the right reads when matched up against bigger defenders. He describes his game as all-around rather than one-dimensional, understanding when to attack and when to move the ball for the benefit of his team.

His favorite player is Kobe Bryant, whom Cunningham admires most for his legendary Mamba Mentality. That mindset, defined by fearlessness, discipline, and relentless work, has heavily influenced how he approaches the game. 

Cunningham openly talks about wanting to “take on every good basketball player,” 

A competitive edge that fuels his confidence heading into each matchup. While he continues to grow into that mentality, his drive to push past his limits during solo workouts reflects the same philosophy. Currently competing with Team Up AAU (17U), Cunningham is entering the upcoming AAU season with a clear focus: give his best effort and compete at the highest level possible. 

“ I just want to try my best.” 

His personal goals include averaging around 15 points per game while continuing to impact the game in multiple ways. Through camps and showcases, including All-American camps, he has tested himself against elite competition, learning both his strengths and areas for growth, such as finishing with his left hand and improving shot consistency.

Despite being homeschooled, Cunningham maintains a disciplined routine, often training independently and dedicating significant time to shooting and skill development. His commitment to working alone, pushing through fatigue, and refining his release highlights his maturity and self-motivation. Coaches and teammates alike have recognized him as a reliable teammate, someone who contributes to winning without needing constant attention.

Cunningham’s résumé already includes notable achievements. He was part of an undefeated championship team, earned three MVP awards in county-level competition, and hit a memorable game-winning buzzer-beater in a pivotal moment. All America also named Cunningham as a top prospect. His story and resilience were also recognized beyond the court, as he was featured in the book "Against Odds: The Resilient Coach  Navigating the Landscape of S.P. O.R.T.S." by Coach Dr. Kevin Wilbon Sr., Ed.D., MAED, MBA, BS, AA, which highlights his journey and perseverance.

Looking ahead, Cunningham has aspirations that extend beyond basketball. He has expressed interest in pursuing engineering at the collegiate level, emphasizing the importance of education alongside athletics. With growing exposure, collegiate interest, and a relentless mindset inspired by Kobe Bryant, Roosevelt Cunningham III continues to carve his own lane, proving that determination, versatility, and mental toughness can turn an unconventional path into a powerful story.