Jason Michael Sheffield

With hearts heavier than words can hold, we share the heartbreaking news of the passing of Jason Michael Sheffield, age 30, of Naples, Florida. Jason left this world on Friday, March 27, after being tragically shot while walking in the woods near his home. His departure was sudden, senseless, and deeply felt by all who loved him.

Jason was born on April 27, 1995, in Dunkirk, New York, to Michael and Debra (Klyczek) Sheffield. From the start, he carried an inner light - a natural gift for lifting spirits and encouraging others to believe in themselves. He attended school in Fredonia, New York, before moving with his family to Naples, Florida, at the age of 8. Jason graduated from Gulf Coast High School in 2013, where he proudly served in JROTC and took on lead roles in school musicals and productions. His voice was exceptional and remembered long after the moment passed.

Jason worked hard to achieve his goals and grow into the man he felt called to be. He earned his Bachelor of Arts in Political Science from Florida Gulf Coast University in 2018, graduating Magna Cum Laude, and proudly served as an intern to United States Congressman Curt Clawson. He went on to earn a Master of Arts in Executive Leadership and Management from Liberty University in 2022.

On July 3, 2021, Jason married the love of his life - his high school sweetheart, Regina (Gilbertson) Sheffield. Together they built a home filled with laughter, music, and joyful chaos. Jason was a devoted and loving father to his children, sons Ashton and Grayson, and daughters Carter and Hazel. He cherished his children deeply, sang to them, wrote songs for them, and was never happier than when he was with them.

Professionally, Jason devoted himself to service. Before becoming Director of Operations for Meridian Contracting LLC, he worked as a Probation Officer with the Collier County Probation Department, guiding individuals toward healthier, law‑abiding lives. He also served as a Senior Screening Analyst for Juvenile Services Program, Inc., and as a Child Protective Investigator for the Florida Department of Children & Families. In every role, he served with a belief in human potential.

Jason was a gifted guitarist, singer, and songwriter. Music was his language of love, one he shared with his children, his wife, his parents, and anyone lucky enough to hear him play. His songs will continue to echo in the hearts of those who knew him.

A man of faith, Jason attended St. John the Evangelist Catholic Church in Naples and was a member of the Knights of Columbus, AJ Corr Assembly 3308. His faith, anchored in God’s love, shaped his character.

Jason is preceded in death by his grandparents, David and Francine Sheffield; grandfather, Richard Spekczynski; and cousin, Michael Bobik.

He is survived by his devoted wife, Regina; his four cherished children; his loving parents, Michael and Debra; and his beloved sister, Katelyn (Evan) Weiss. He is also survived by his grandparents Walter and Nancy Klyczek; grandmother, Bonnie Spekczynski; and a large, close-knit family of aunts, uncles, cousins, and dear friends who will forever carry his memory forward.

Jason was an extraordinary man who lived a life marked by love of family and service. Though his time with us was far too short, the impact he made on his family and on every life he touched will endure.

A Funeral Mass will be held at St. John the Evangelist Catholic Church, 625 111th Avenue North, Naples, FL 34108, at 11:00 a.m., Monday, April 13, 2026.

Arrangements are entrusted to Hodges Funeral Home at Naples Memorial Gardens.