Jesse Lee Penn

Jesse Lee Penn 88, passed away peacefully at his daughter’s home in Lexington Ky on Thursday September 7th, 2023. Jesse was born in Frankfort, Kentucky on October 18, 1934, to the late Oather and Edith Penn. He graduated from Bald Knob High School in 1953 and married his school sweetheart, Wilma Wood (Craycroft). Together they had three children Gary, Greg, and Trina. Jesse was always interested in family business opportunities. In his younger years he and his father started Penn’s Auto Service which then led to opening Penn’s Wrecker and Salvage business. He spent many days and nights running this business with his dad, along with teaching his two sons everything about auto mechanics, the value of hard work, and how to run a successful business. Years later, Jesse married his second wife Judy Caldwell Penn, they had a daughter Katie and stepson Jeff. They continued to work in the auto business by running and operating Penn’s Auto Parts. In 1992 Jesse decided to join his son’s Greg and Gary and purchased Columbia Steak House from the Calumet Farms family. He soon realized he enjoyed the restaurant business, so he purchased and ran Shooters Bar and Grill up until 1998. Two other side interests that gave him much joy, was owning and being involved with rental property and running a vending business with his good friend Marvin. Jesse lived a life full of hobbies and interests and was very active in in his church community. He was an avid member of Boone Plaza Church of Christ where he taught Sunday school and lead the worship service. He later joined the Revival Tabernacle Church and continued to attend until he fell into poor health. One of the biggest joys in his life was his love of music. He played the guitar, mandolin, and fiddle. He was a big influence in his daughter Kati’s career as a professional fiddle player. He loved bluegrass music and traveling to watch her perform at many venues. No matter where Kati was playing across the country, Jesse would be right there to applaud. He also loved to hunt, fish and travel and spent many weeks on the road with friends and family traveling the country in search of the ultimate fishing hole. Jesse was a member of the “Campbell House Breakfast Club” where he met and made many lifelong friends. Everyone who knew Jesse knew him as a very funny and colorful man who always had a good story, a funny joke or catchy phrase that had been handed down over the generations. He loved all his children and grandchildren and always treasured family times together. Jesse’s passing leaves a void in the lives of those who knew and loved him. His memory will be cherished by all who had the pleasure of knowing him. Jesse is survived by his children: Gary (Tricia) Penn, The Villages Florida; Greg (Lisa) Penn, Lexington Ky; Trina Penn, Lexington Ky; Kati (Justin) Jenkins, Burgin Ky; stepson, Jeff Caldwell, Winchester Ky. He is also survived by seven grandchildren, Ashley Raymond, Justin Penn, Gabriel Penn, Tyler Penn, Sydney Robinson, Ethan Penn, and Jessi Leigh Hopper. Two brothers, Melvin Devine Penn (Sandy), Paul Penn (Ellen, deceased); and 6 great grandchildren and a host of loving nieces and nephews. In addition to his parents, Jesse was preceded in death by his second wife Judy Caldwell Penn, and sister Faye Metts. Visitation will be held at Harrod Brothers Funeral home, 312 Washington Street Frankfort Ky on Sept 13th from 6:00 PM – 8:00 PM. Funeral will be held at 12 noon on Sept 14th at Harrod Brothers Funeral home, followed by burial at Sunset Memorial Gardens, Frankfort Ky. Serving as pallbearers will be Bradley Penn, Justin Penn, Gabriel Penn, Tyler Penn, Ethan Penn, and Scottie Penn. Honorary pallbearers will be Kenneth "Shorty" Watkins, L.T. Harrod, Tim Blair, and Jamie Manns. Arrangements are under the direction of Harrod Brothers Funeral Home & Crematory. Condolences may be shared via the online guestbook at www.harrodbrothers.com

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Jesse Lee Penn

October 18, 1934 - September 7, 2023