Arts & Entertainment
IFFBoston Highlight: Hungry, Humble & Focused
A local documentarian honors a Roxbury basketball team and its father-figure coach in "Push: Madison vs. Madison."

Attendees of “Push: Madison vs. Madison” poured into the two-level viewing room of the Somerville Theatre this past Saturday night. Locals greeted one another as Coach Dennis Wilson, the real-life lead of the documentary, walked up and down the aisles shaking hands with former students and neighborhood friends. It was a family affair – and Coach Wilson, a Roxbury-native, was the patriarch.
The film tells the story of the 2007 undefeated season of Roxbury’s Madison Park Vocational High School basketball team. It follows the Madison Park Cardinals and their attempt at a first-time state championship, while uncovering each player’s personal struggles of living in the inner-city.
Raheem Singleton, Jakeen Cobb, and David Daniels, former members of the team and lead roles in the film, endured neighborhood and domestic violence, family drug-abuse, and the loss of parents and role models. A large part of the team’s success can be attributed to the strength of Coach Wilson – a teacher, coach, and Dean of Discipline with over 40 years of experience.
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“I would convey to the team that team success will enable individual success,” Wilson said in an interview. “And that everyone must make sacrifices in the classroom, and on and off the court.”
Much like the star of the film, Director Rudy Hypolite is a veteran of his craft. He’s been creating films for over 20 years and has served as a Multimedia Producer at Harvard University for over 15 years. After working with Coach Wilson on a local sports cable program and learning of his 2007 season and story – he decided to create his next documentary.
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“I felt it was a good opportunity to follow the journey of a team with prospects to win a championship,” Hypolite said. “But I also saw a chance to highlight the issues facing the inner-city and students of color in the Boston public school system.”
The film’s style is one of gritty documentary footage, which takes audiences behind all closed doors of the team during the 2007 season, and face-to-face with the tireless efforts of its key motivator and coach. It leaves viewers with the notion that the story, although compelling, is a small piece to a much greater issue – one that the film’s director and lead hero continue to remain real-life advocates for.
“A few individuals can help change a negative impact on our youth,” Wilson said. “They need to be exposed to successful people that have come from their community, neighborhoods and circumstances.”
"Push: Madison vs. Madison" will be featured at The Roxbury Film Festival July 28 - 31. Follow the film on its official website for updates and news on other showings and releases.