[1] Most recently, he played a part in helping the Cleveland Cavaliers win the 2016 NBA Finals over the Golden State Warriors.

Jim started at point guard his first two years at Assumption, 1973–1977, leading the team to a third-place finish in the national championship tournament both seasons.

He played point guard at Marquette, where he helped the Warriors win the 1977 NCAA Men's Division I Basketball Tournament (Marquette's only championship) by scoring 14 points in the National Championship Game versus the North Carolina Tar Heels.

[3] Boylan began his coaching career as a player-coach in Switzerland from 1982 to 1986 and led Vevey Basket to its first championship in its 30-year history.

After Skiles was fired in 2002, Boylan worked with Terry Stotts for the Atlanta Hawks during the 2003–04 NBA season.

On December 27, 2007, after the firing of Scott Skiles, Jim was named the interim coach for the Bulls for the remaining season.

He would later on be a part of the 2015–16 Cleveland Cavaliers squad to earn an NBA Finals championship over the 73–9 Golden State Warriors.