Kokomo, IN – Jackie Wade Dailey, a man who lived life at a full gallop, crossed the final finish line on Feb. 15, 2026, at the age of 61, in Kokomo, Ind.
Born on Oct. 4, 1964, in Washington Courthouse, Ohio, Jack was the kind of soul who could light up a room faster than a flashbulb at a racetrack.
Affectionately known as the family’s very own Seabiscuit, Jack was a master driver and trainer as a member of the United States Trotting Association in Ohio. His love for horses was only matched by his passion for mowing – yes, you read that right – mowing everyone’s lawn for free. It’s safe to say, Jack never met a blade of grass he didn’t want to cut or a person he wouldn’t help.
Jack was the cherished son of Alice Cox and the late James Dailey, and he shared his zest for life with his beloved companion Sheila Wright. He was a father figure not just to his own kids, Tiffany Dailey (Kylie), Nichole Castillo (Philip), and Brianna Britton (Tyler), but also to his bonus son Kenny Wright (Jerica). His grandchildren – Lillie, Kenslie, Vivian, Khloe, Jenson, Isabella, Lydia, Cole, Shaylyn, Zaylee, Marley Wade, Nevaeh, Ryland, Philip, and Wyatt – were the apples of his eye, and he was always there to cheer them on, whether from the sidelines or the front row of their life’s grandstands.
Jack was the brother who had mastered the art of the prank and the tender touch in equal measure, leaving his siblings Angie and Angel Dailey, Jared Dailey (Jill), John Dailey (Terri), Jeff Dailey, and Jody Dailey with a treasure trove of laughter-filled memories. His sister-in-law, Kim Dailey, also held a special place in his heart. Jackie now joins his father James and his brother Bill in the great paddock in the sky.
To say Jack was loving, passionate, and generous is like saying the Kentucky Derby is just another horse race. He was the life of any party and the first to lend a hand. His absence will be felt deeply, but the starting gates of heaven have never been more jubilant to welcome a new champion.
Jackie Wade Dailey’s legacy is not just in the races won or the horses trained, but in the countless lives he touched with his boundless energy and his unwavering commitment to his family. His was a life well-ridden, a race well-run, and a victory lap that will echo in the hearts of those who loved him forever.
So, as we bid farewell to Jackie, let’s not say goodbye. Let’s say, “Until we meet again at that great winner’s circle in the sky.” Rest easy, Jack, and know that your track record of love and laughter remains unsurpassed.