He argued the U.S. Supreme Court case Blyew v. United States and served as the president of the University of Louisville from 1869 to 1885.
He attended local schools and then worked for three years in his father's clerk's office.
[1][2] In 1870, Caldwell fought for the business interests of Louisville & Nashville Railroad when the Kentucky legislature considered giving the Cincinnati Southern Railroad the central Kentucky right of way.
[1] In 1872, Caldwell opposed the federal authority in Kentucky civil rights and argued the case Blyew v. United States before the U.S. Supreme Court.
While he was president, the university joined the Association of American Medical Colleges and he helped raise the standards of admission and graduation.