OAK awards are presented to outstanding alumni of Kentucky colleges and universities who have gained national recognition in their profession or through their civic endeavors and have shown a continuing commitment to their alma maters.
Caldwell, a Lexington resident and a native of Lincoln County, was named Assistant U.S. Attorney for the Eastern District of Kentucky in 1987. In 1991, at age 35, she became the first woman in Kentucky—and the youngest woman in the nation—to serve as a U.S. attorney when she was named to that position for the Eastern District of Kentucky. In that role, she earned a reputation for fighting public corruption when she led several investigations that resulted in the successful prosecution of state officials. She was recognized by the Department of Justice for her efforts in the investigation.
Caldwell returned to private practice in 1993 specializing in civil and criminal litigation at one of Kentucky’s leading firms. Due to her quality work and reputation for successfully fighting public corruption, President George W. Bush nominated her to the federal bench in 2001. She was unanimously approved by the U.S. Senate to serve as U.S. District Judge for the Eastern District of Kentucky where she continues to serve today.
"As busy and accomplished as Karen is, she continues to consistently support Transylvania,” President Charles L. Shearer said. "She delivered the commencement address to the Class of 2005 as part of Transylvania’s 225th anniversary celebration, and she received an honorary doctor of laws degree in recognition of her service and professional achievements.”
Caldwell has been a member of Transylvania’s board of trustees since 2001 and has served as a member of the Alumni Executive Board, the president of the Bluegrass Area Alumni Club and as an adjunct professor. She has given and helped raise money for several projects, including the establishment of an endowed scholarship fund for students to study abroad. Caldwell is a recipient of Transylvania’s Distinguished Services Award.
The Kentucky Bar Association presented Caldwell with its Outstanding Lawyer Award in 1995, and she was named one of the Top Women in Business in Lexington in 1994. She has served on boards and committees for numerous organizations including the Fayette County Ethics Commission, Prevent Child Abuse Kentucky, Lexington Ballet, Kentucky Board of Bar Examiners Character and Fitness Committee and the Kentucky Commission on Women among others.
Past OAK winners from Transylvania include Lois Gray in 2004, Edward Eckenhoff in 2002, and Clyde Roper in 1998.