Jason Wade Stogsdill

Jason Wade Stogsdill

August 20, 1969 – January 29, 2025

In loving memory of Jason Wade Stogsdill, a cherished son, friend, and an inspiration to all who knew him. Jason passed away on January 29, 2025, after a brief illness. His radiant spirit touched countless lives, and he will be remembered for his kindness, sharp wit, genuineness, and unwavering dedication to the people, animals, and causes he held dear.

Born on August 20, 1969, in Bloomington, Indiana, to Donna Irene Stogsdill, Jason brought joy and warmth from the very start. He attended Marlin Elementary School, University Middle School, and Bloomington High School North (Class of 1987) before earning a bachelor’s degree with a double major in political science and criminal justice from Indiana University in 1992. A lover of learning and people, Jason formed lifelong friendships at every stage of life.

Jason enjoyed a successful career in sales and the insurance industry, working with Bloom Health Insurance Agency, LLC, and Tranzact Insurance, before transitioning to banking in 2018. In 2014, he relocated to Rotunda, Florida, to be closer to his beloved mother, Donna. Their relationship was one of love, laughter, and playful teasing, built on a bond that was deep and unshakable.

In 2021, Jason founded Jason’s Rides, LLC, where he not only safely transported clients but also formed lasting connections. His stories of the remarkable people he met and the many clients who became regulars reflect the profound trust and respect he inspired. A fierce advocate for human rights and a protector of people who are marginalized and underserved, Jason’s selflessness and courage often led him to put others’ safety before his own—true to his nature of always caring for others.

Jason has a deep passion for sports and was a naturally gifted athlete. From a young age, he showcased his talent across various sports. At just five years old, he became a racquetball champion. He played basketball for a Boys Club team and excelled as a shortstop in both Pony League and Little League at Danny Smith Park. As a child, his admiration for athletes was so strong that he once pleaded with his mother to marry Scott May, the star of the IU Hoosiers’ undefeated 1975-1976 national championship team – he was completely baffled as to why she couldn’t make it happen!

An avid golfer, Jason spent countless hours on the greens at Cascades and Eagle Point in Bloomington, Indiana, and at courses across Florida. He was a PGA pro who taught golf and shared his love of the game with others. His passion for golf was matched only by his devotion to his mother and his beloved dogs—Seve, who passed in 2023, named after Seve Ballesteros, and Cerberus, affectionately called Cerby.

Though Jason’s time with us was far too brief, his legacy of kindness, compassion, and love endures. In our grief, we take solace in the memories of his laughter, his generosity, and the joy he brought into our lives. His spirit inspires us to live with the same authenticity, bravery, commitment, warmth, and enthusiasm he did.

Jason is survived by his loving mother, Donna Irene Stogsdill, and her husband, Dave Harris; his loyal pup, Cerby; his “less attractive twin,” Brad Pitt (as Jason humorously claimed); and the many friends who cherished him. He leaves behind a world forever brighter for having known him.

Jason’s ashes will be interred this summer in his family’s plot at Harris Cemetery in Johnson County, Indiana. A Celebration of Life will be held in Indiana later this summer, with details forthcoming.

"To honor Jason’s memory, in lieu of flowers or donations, take a friend to lunch and share a funny Jason story—an act he would have loved! Messages to Jason’s family can be sent via email to [email protected] or shared on this memorial site.

Rest in peace, dear Jason. May you find joy playing golf and watching West Wing reruns with your beloved Seve out there. You are deeply missed and forever remembered with love.