Calderon, 40, appeared in 57 games with the Cavs during the 2017-18 season. He signed with the Pistons the following season and played 49 games before retiring.
He most recently served as special assistant to the executive director of the NBA Players Association.
The Cavs did not offer many specifics on Calderon’s role with the team, merely stating that he will assist president of basketball operations Koby Altman and the front office to “achieve their goals both on and off the court in a variety of engagements.”
Calderon’s playing career began with the Raptors in 2005. He also spent time with the Hawks, Lakers, Knicks and Mavericks, as well as playing professionally in Spain.
“We are thrilled to add someone of Jose Calderon’s background and experience to our front office,” Altman said in the statement. “His accomplishments as a basketball player and familiarity with our organization will be invaluable.
“We look forward to his insights and perspective on how we can continue moving this team forward and enhancing our efforts towards sustainable and long-term success here in Cleveland.”