Caywood Prewitt


Caywood Prewitt has over 25 years of litigating cases involving bodily injury, insurance disputes, bad faith, and contract law. He has tried cases in a large number of jurisdictions from the coal fields in Eastern Kentucky to the Commonwealth’s urban areas in Lexington, Northern Kentucky and Louisville. He has extensive legal knowledge in the areas of automobile accidents and insurance, trucking accidents, premises liability and unfair claims settlement practices. Prior to practicing law, Caywood taught college level English literature and composition. In his spare time, he enjoys restoring a Victorian era home in downtown Lexington, travel, University of Kentucky Basketball, listening to a wide variety of music (Messiaen to Iggy Pop), reading obituaries, and cooking.

Education and Memberships

University of Kentucky (B.A., 1986; M.A., 1989, J.D., 1993) Moot Court Board, 1992-93 International Moot Court Team, 1993 Kentucky Bar Association, 1993 to present Fayette County Bar Association, 1993 to present

Honors and Awards

AV Rating, Martindale-Hubbell, the highest level of competence and ethics as voted on by legal piers Super Lawyers®

Community Service

Christ Church Cathedral, Verger: 2015 to present Member of Vestry: 2015-2017
Junior Warden: 2016
Senior Warden: 2017
Finance Committee: 2018
Special Projects Committee: 2019 to present Church Under the Bridge, Board Member for homeless ministry, 2015 to 2017 Moveable Feast, Volunteer for homeless food ministry, 2016 to 2019 Lafayette Senior High School
Choir Boosters Board of Directors: 2015 to 2018
Chair: Committee to Redraft Bylaws


Phone: (859) 255-6885

              ext. 108