Stephen Carl Cawood

Stephen Carl Cawood, prominent Eastern Kentucky attorney from Pineville, passed away in Lexington, Ky., on October 17, 2025, after a valiant battle against cancer.

Steve was born on October 14, 1943, and attended Pineville Independent Schools, graduating in 1961. During his teenage years he was the editor of the yearbook and earned the Eagle Scout Award. Steve was inducted into the Order of the Arrow, later serving as lodge chief of Mischa Mokwa. In addition, he was a Vigil Honor recipient of the Order of the Arrow.

Steve was a lifelong Presbyterian following in the tradition of his grandparents. He was a member of First Presbyterian Church of Pineville where he was honored to serve as both a Deacon and Elder.

Steve attended Eastern Kentucky University as an undergraduate, majoring in political science and minoring in history and geology. He was a member of the Polity Society, the Collegiate Council on United Nations and the Young Democrats. He served on weekends and in the summers as an Appalachian volunteer providing services in remote areas close to his heart, a commitment to the region that continued throughout his adult life.

Steve graduated from University of Kentucky’s School of Law in 1968. During his law school summers, he continued serving Appalachia. In the spring of 1968, he joined the tour group Robert F. Kennedy led in Eastern Kentucky to highlight the plight of local people. His photograph of Kennedy in the Fleming-Neon gym in Letcher County, Ky., appeared in the New York Times.

While in law school, Steve married the love of his life, Jeanette “Sissy” McCauley of Middlesboro. In the fall of 1968, after a summer at Tufts University in Boston, they moved to West Point, Miss., to become faculty members at Mary Holmes College, a small Presbyterian college serving Black students. While there, they met Fanny Lou Hamer, future congressman John Lewis and Julian Bond, all of whom were active in the civil rights movement and came to Mary Holmes to meet with and encourage many first-generation college students.

After working in Atlanta briefly with the Presbyterian Church’s social welfare arm, they returned to Kentucky to follow up on their commitment to serve Appalachia. Steve was instrumental in the organization of Appalachian Research & Defense Fund (known today as AppalRed) the 50-year legal aid service that continues today providing free legal services to 37 counties in the Appalachian Mountains.

In 1973, Steve opened his Courthouse Square law office, following in the footsteps of his grandfather, Judge James Gilbert. Over his long legal career, no client was too big or too small. Whether a large corporation with national recognition or a local miner who had developed black lung from the mines, Steve was willing to fight for his clients. His interest in bettering conditions for his neighbors led him to enter the legislative race in 1979 for the House of Representatives. During the 1980 legislative session, he was voted “Outstanding Freshman Representative” by the Capital Press Corps. Steve distinguished himself as the first freshman legislator to chair a committee, resulting in the passage of Kentucky’s Surface Mining Act.

In 1989, Steve received the honor of being named a Commissioner from Kentucky to the Uniform Law Commission, a national organization dedicated to creating uniform acts for adoption by state legislatures throughout the nation. He both chaired and served on numerous committees, including one he initiated to provide reciprocity among states in recognizing licensure for medical staff seeking to volunteer to provide medical care following disasters. After serving 20 years, he attained Life membership in the organization. Many valuable friendships were made and enjoyed through the years that remain to this day.

Steve’s commitments to his hometown and the Commonwealth of Kentucky were evident in many areas. He most recently served as a Board member with the Kentucky Historical Society’s America 250 project, celebrating and exploring Kentucky’s history from the nation’s founding to today. His knowledge of Kentucky history and geography was hard to match. He served 12 years on the renowned Prichard Committee for Academic Excellence, working alongside other Kentuckians to reform education in the Commonwealth. On the local level, Steve was elected to the school board, serving his alma mater. During his tenure as Pineville Independent’s board chair, the Commons area was designed and built, connecting the old school with the addition. This space is frequently used to gather students, parents, alumni and community members. In 2023, Steve was inducted into the Pineville Schools’ Hall of Fame as an outstanding graduate. This award was one he most cherished.

Steve’s lifetime hobbies of collecting coal mine scrip and model railroading are well known among his friends and fellow hobbyists. He was a longtime member of the National Scrip Collectors Association and served several terms as president. He wrote many articles for the L&N Railroad Historical Society publication and served as a member of the Chattanooga-based L&N Historical Society as well as Counsel to the Board. Steve was instrumental in recently moving the L&N archives to Chattanooga, where they will be permanently housed.

Steve’s vast knowledge of Appalachian issues earned his placement on the Bell County Historical Society Board of Directors, a position he relished and actively participated. His concern for the environment generated his interest in assisting the Kentucky Natural Lands Trust to acquire land in Bell and Harlan counties as part of the Blanton Forest Reserve. Those who knew him in his home surroundings knew of his voracious reading of history and biography, his love of birds and the joy his kitchen garden brought him. He and Sissy loved to travel as often as they could. A highlight was a visit to Cawood, Yorkshire, England and riding the British rails. Bluegrass music was a lifelong love of his, particularly Dale Ann Bradley, a “local girl” as he called her.

Steve was preceded in death by his parents, Sophia Elizabeth (Gilbert) and Murrell Cawood; his brother, Thomas Cawood; and his sister, Amanda Jane Brooking.

Steve is survived by his wife, Sissy; their two daughters; Beth (Bill) Overman and Mandy (JD) Hickey; and their five grandchildren, Charles William Overman, Jr., and Caroline Cawood Overman of Lexington, and Henry Christopher Hickey, James Cawood Hickey, and Andrew McCauley Hickey of Lookout Mountain, TN.

He is also survived by his brothers and sisters-in-law, John and Becky McCauley who provided wonderful care to him and Sissy in his last months, Dr. Joseph L. McCauley and Cornelia Kueffner, Mary Kaye McCauley, and William B. McCauley. Steve was a proud cousin as well as uncle to many nieces and nephews including his brother and sister’s children, Biff Brooking, Ginny Brooking Jenkins and Candace Cawood Webb (Jason). His close friends supported him in many ways—to them the family offers its sincerest thanks.

Visitation will be held in Pineville at St. Anthony’s Parish Hall on Sunday, November 2nd, 2025, from 1:00 - 3:00 PM.

Funeral Services will be held November 3rd at 1:00 PM at the Pisgah Presbyterian Church, 710 Pisgah Pike, Versailles, Ky. Family will receive friends immediately following the service at a reception on-site.

In lieu of flowers, those inclined may consider donating to the Bell County Historical Society, Middlesboro, Ky.; Kentucky Natural Lands Trust, Berea, Ky.; or the L&N Historical Society, Chattanooga, Tn.

The family expresses its deepest gratitude to his niece, Candace Cawood Webb, RN, Reece Schenkenfelder, RN Leader, Dr. Martha Combs-Woolum, Dr. Thomas Slabaugh, Jr., Dr. John Fox, and special family friend, Tammy Howard.

Arnett & Steele Funeral Home and Cremation Center in Pineville is honored to serve the Cawood Family.