A Courier Journal report on Caldwell's appointment as U.S. attorney in 1991 noted that she had dated senator Mitch McConnell.[2] McConnell, who recommended Caldwell for that position, said at the time that she was well qualified and should not be barred from the position because of their personal relationship.[3]
Federal judicial service
Caldwell was nominated by PresidentGeorge W. Bush on September 4, 2001, to a seat vacated by Henry Rupert Wilhoit Jr. She was confirmed by the Senate on October 23, 2001, and received her commission on October 24, 2001. She served as Chief Judge from October 15, 2012, until August 2019.
In 2007, she was honored by the University of Kentucky College of Law and the Kentucky Bar Association by being inducted into the college's Hall of Fame.[4]