Caldwell was born in Detroit, Michigan and attended Pershing High School. He was a standout player in high school and was named to the All-City team in 1962. He then attended Arizona State University, where he was a two-time All-American and led the Sun Devils to the NCAA Final Four in 1963.
Caldwell was drafted by the Detroit Pistons in the 1964 NBA Draft. He played for the Pistons for three seasons before being traded to the St. Louis Hawks in 1967. He was a two-time All-Star with the Hawks and was named to the All-NBA Second Team in 1969. He was traded to the Atlanta Hawks in 1971 and played for the team until 1975.
Caldwell was known for his athleticism and his ability to score. He was a great rebounder and was a solid defender. He was also known for his leadership and was a key part of the Hawks' success during his time with the team.
Caldwell retired from the NBA in 1975 and went on to become a successful businessman. He was inducted into the Arizona State University Sports Hall of Fame in 1988 and the Michigan Sports Hall of Fame in 2005. He passed away in 2015 at the age of 73.
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