Dillard Young Caldwell, Jr. was born in Versailles, Kentucky on June 15, 1970. His involvement with the military during the Gulf War led to a later diagnosis of Stage 4 lung cancer. After battling this for a number of years, he was welcomed into heaven on Friday, January 17, 2025, in Tarpon Springs, Florida surrounded by his family at the young age of 54. Dillard used the short time that he was given on earth with much wisdom and intent. He left this world better than he found it and had the heart of a servant. He served God, his country, his community, and his family with integrity, goodness, and honor.
Dillard enlisted and proudly served in the US Army. He was a gallant and decorated war time veteran serving in Germany, Saudi Arabia, and Iraq; he earned the following honors:
Army Service Ribbon, National Defense Service Medal, Southwest Asia Service Medal, W/2 Bronze Stars, Army Achievement Medal, Rifle Expert Marksmanship Badge, M16 Expert Marksmanship Badge, Expert Infantryman Badge, and a Combat Infantry Badge.
Education was a significant part of Dillard’s life. He earned several degrees including an Associate Degree in Dental Laboratory Technology, a Bachelor’s Degree in Exceptional Student Education and he earned his Master’s Degree in Educational Leadership. Dillard began his career with the Pasco County School System in 2000 and retired from his position as Assistant Principal at Anclote High School in 2023. During his time there, in addition to teaching and administrative duties, he coached numerous high school sports teams.
Being an educator and administrator was more than a job to Coach Caldwell. The campus was a mission field where he shared a message of encouragement, genuine interest, and love for his students and faculty. The impact that Mr. Caldwell made in his 23 years of service is impossible to gauge. He was honored by the Pasco County Sheriff’s Office in 2005 and again in 2022 with the Leader of Youth Award. The incredible outpouring of messages during his illness from students and faculty alike give a small glimpse into the depth of the remarkable work that he accomplished in his community.
Outside of school you would find him at the shop working on cars or on the boat soaking in the saltwater and sun on Anclote Island. He loved football, basketball, and was a diehard Kentucky Wildcats fan with a vast collection of memorabilia and royal blue clothes. Dillard enjoyed long days on the water and nights out for local live music and a drink with friends. He was known to have great dance moves, corny dad jokes, and an infectious laugh. He would flash his charming smile along with a hang loose hand gesture and affectionately call his friends duuude.
Dillard filled many different roles and held great titles: Coach, Mr. Caldwell, Dilly and D. He was a son, a brother, and an uncle but his most important titles were Dad, Pappy, and Husband.
He loved our country, his community, and the Cats, but if you spoke to him for more than a moment, you would quickly realize that nothing else in his life came close to his family.
He adored his beautiful wife of nearly 35 years. Dillard and Maribeth were soul mates in every way. Together they created and raised a handsome family and built a warm and welcoming home widely known as Casa de Caldwell. They lived a life of commitment to one another, God, and community as an example to their children.
Dillard leaves behind a rich legacy for his survivors; his wife, Maribeth, their children, Cameron (Gretchen) Caldwell along with their three children Rylee, Kennedy, and Braxton, Conner (Morgan Lee) Caldwell, and Corbin Caldwell, his mother, Maggie (Frank) Tanner and father Dickey (Regina) Caldwell, his brothers Phillip Caldwell and Jason Caldwell and sister Heather Long, his mother-in-law, Sandy Anderson and sister-in-law Suellyn (Rick) Wilson along with numerous aunts, uncles, nieces, nephews, and close friends.
The family would like to thank David Bolton of Trinity New Life Church and Edward Kellum of Faith Methodist Church of Hudson for the prayers, support and ministry throughout the last few years.
While Dillard’s absence from this life will forever leave a void in the hearts of those that loved him, there is assurance and peace in the knowledge that he had a relationship with Jesus Christ and is now ultimately healed with Him.
https://everloved.com/life-of/dillard-young-caldwell/obituary/
