He served as the head coach of the Portland Trail Blazers and general manager of the Detroit Pistons and Minnesota Timberwolves.

He left school to serve in World War II as a lieutenant commanding a landing ship for the Marines.

[2] McCloskey also spent time in Eastern Professional Basketball League (EPBL), including with the Sunbury Mercuries.

His best-known moves were drafting future Hall-Of-Famer Joe Dumars outside the lottery and rebounding champ Dennis Rodman in the second round of the NBA Draft, trading three players for future all-star center and dominant rebounder Bill Laimbeer and trading superstar Adrian Dantley for Mark Aguirre during the 1988–89 season, a move that helped the Pistons win the NBA championship in 1989 and 1990.

He acquired Darrell Walker, Brad Sellers, and Orlando Woolridge, and let go of Vinnie Johnson and James Edwards to try to make the team younger.

The Pistons struggled with their chemistry, as key subs like John Salley did not improve their performance, yet they won 48 games.