Chiesa's career began as the athletic director and head basketball coach at his alma mater of St. Thomas Aquinas College, where he guided the Spartans to three 20-win seasons and several postseason tournaments. Following his tenure at St. Thomas Aquinas, Chiesa served as an assistant coach at Dartmouth from 1979 to 1981. He then accepted the head coaching position at Manhattan College, where he coached from 1981 to 1985 and was named the Metro Athletic Conference Coach of the Year in 1983. Chiesa joined Rick Pitino's staff at
Providence College as an assistant coach from 1985 to 1987, before becoming head coach for the 1987–88 season. After posting a miserable 11–17 record, Chiesa was replaced as head coach by
Rick Barnes who the following season posted an impressive 18–11 record and led the same team to the first round of the
NCAA Division I men's basketball tournament. He joined the
Orlando Magic on August 30, 2012, as special consultant to the head coach. He previously served as a consultant for the
NBA Development League for the previous two seasons (2010–12). During his coaching career, Chiesa served as an assistant coach for two Hall of Fame coaches –
Jerry Sloan with the Utah Jazz and
Rick Pitino at Providence College. Chiesa is one of a select few assistant coaches to serve in both the
NBA Finals (1997 and 1998) and the
NCAA Final Four (1987). Chiesa was inducted into the
Hudson County Sports Hall of Fame in January 2001 for his achievements as a college and professional basketball coach. He was also inducted into the New England Basketball Hall of Fame in September 2009. ==Personal life==