Vaccaro is probably best known for his tenure with Nike, Inc., where he signed Michael Jordan to his first sneaker deal. Vaccaro left Nike for Adidas, then Reebok. He founded the ABCD All America Camp, an elite showcase of high school basketball standouts, which ran from 1984 to 2007. It featured future stars Kobe Bryant, Dwight Howard, and LeBron James. Vaccaro cofounded the first national high school All-Star game, The Dapper Dan Roundball Classic, with concert promoter and boyhood friend Pat DiCesare in Pittsburgh in 1965. The game endured for 43 years and its alumni includes such greats as Calvin Murphy, Shaquille O'Neal, Kobe Bryant, Chris Webber, Alonzo Mourning, Kevin Garnett, Vince Carter, Tracy McGrady, Patrick Ewing, Rasheed Wallace and Stephon Marbury.
An ESPN 30 for 30 documentary about Vaccaro entitled "Sole Man" aired on April 16, 2015. Vaccaro had a rivalry with George Ravelling over summer high school basketball. Vaccaro was a key figure in the O'Bannon v. NCAA lawsuit, which allowed players to be compensated. Vaccaro helped to recruit Ed O'Bannon for the case.
- Thamel, Pete (June 24, 1977). "Marketing All-Star is Ready to Relax". The New York Times.
- Prisbell, Eric (July 6, 2007). "Camps Turn To Skills, Rather Than Thrills". Washington Post.
- "The Grassroots Godfather".
- A classic showcase for high school talent. Dick Vitale. SPECIAL TO ESPN.COM