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James Madison High School served as the old stomping grounds of former NFL players Vince Young and Robert Royal and the first Painting with the Pros event. Since 2017, the NFLPA's Super Bowl weekend philanthropic event features active and former players cultivating creativity and mentorship with local high school students while engaging in a canvas painting activity. "It means a lot," said former NFL QB Vince Young on the event being hosted at his old high school. "Being back in the community where it all started. To see it in person as well as NFL guys coming out and seeing where I'm from. I thought it was a really good blessing, and I'm glad the NFLPA chose Madison, my hometown". 

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