[5] Caldwell was a 1940 graduate of Muskingum College where he majored in economics and was a member of the school's debate team.

Following the firing of Lee Iacocca in July 1978, Caldwell became president of Ford Motor Company on October 16, 1978.

[7][8] On October 1, 1979, Henry Ford II retired as CEO[9] and as chairman of the board of directors on March 13, 1980; Caldwell succeeded him in each position.

[10][11] As Chairman of the Board and CEO, Caldwell approved and oversaw the development and launch of the Ford Taurus (and its corporate sister the Mercury Sable) which were introduced to the media days before his retirement,[12] thus allowing him to take public credit for the Taurus program, which became one of the biggest successes in automobile business history.

[13] On February 1, 1985, Caldwell retired from Ford,[14] He later accepted a position as senior managing director at Shearson Lehman Brothers in New York.