Jerome “Jerry” Gemskie
Jerome “Jerry” Harold Gemskie, age 86 of Kissimmee, Florida passed away peacefully Friday, September 12, 2025. He was born in Chicago, Illinois to the late Walter and Anna Gemskie.
Jerry was a born jokester — the kind of guy who could turn even the most ordinary moment into a laugh-out-loud story. He had a kind soul and a knack for helping anyone who needed a hand (often while cracking a joke at his own expense).
Public service was one of Jerry’s greatest joys. He served ten years as a Kissimmee City Commissioner, a role he absolutely loved. He poured the same energy into the Kissimmee Rotary Club, H.O.M.E., the League of Cities Board, Relay for Life, Give Kids the World, and even started Ornaments on Parade in Kissimmee.
In 1995, he and his wife Nancy moved to Florida from Chicago. They enjoyed 31 years of adventure together until her passing in 2011. Their love and laughter filled every chapter of their marriage.
Jerry lived for creating memories. He organized epic white-water rafting trips to West Virginia’s New River — sometimes filling two buses with friends and family. If you weren’t on the bus at departure time, he left without you (he had a schedule to keep!). Rafting took him far and wide: North Carolina, upstate New York, Idaho, Wisconsin, and Costa Rica.
Disney always had Jerry’s heart. Long before the move to Florida, he made sure the family logged plenty of miles to Disney. When Space Mountain debuted in 1975, he hustled the family through the gates so they could ride within the very first hour — because in Jerry’s book, fun ran on a schedule. Years later, he and Nancy even set sail on Disney’s inaugural cruise (the kids are still convinced their invitations got lost in the mail).
Sports brought out Jerry’s competitive streak — and his creativity. He quarterbacked more than a few victorious “Turkey Bowl” teams, on which his son and son-in-law played. He also coined the name and was proud to coach his son and son-in-law’s flag football team, the famous “Aardvarks” out of Chicago in his later sports years. No one wanted to be an “Aardvark”- until they started winning tournaments all over the Midwest!
Jerry was almost never caught without a $2 bill tucked in his pocket — and he made a game of handing them out. His favorite challenge was pointing to the back of the bill and asking, “How many people signed the Declaration of Independence?” (The answer is 56, but Jerry swore a few were in the bathroom when the picture was taken.) Whether you nailed it or wildly guessed, you still walked away with the bill — because for Jerry, the fun was in the giving.
Jerry’s presence was a blessing to all who knew him. His humor, generosity, and zest for life will live on in every story retold, every adventure planned, and every $2 bill tucked into a lucky hand. He will be deeply missed and forever loved.
He is survived by his son, Todd (Chandra) Gemskie of Woodridge, Illinois. Daughters; Kelly (Mike) Boyle of Naperville, Illinois and Darcy MacConnell of Belleville, Michigan. He was blessed with eight grandchildren; Cassidy Boyle, Ryan Boyle, Zoey Schreiner, Joshua Schreiner, Ainsley Schreiner, Jacob (Shelby) Hauge, Madelyn Kreyer and Tyler Kreyer and two great grandchildren; Haelyn Hauge and Hudson Hauge. He leaves behind lifelong friends Danny and Nancy Sexton of Kissimmee, Florida and countless others as he touched so many of the lives around him.
He was preceded in death by both of his parents; Walter and Anna Gemskie. Wife; Nancy Fay Gemskie. Brothers; Walter Gemskie, James Gemskie and Charles “Chuck” Gemskie.
The family invites donations to the V Foundation at V.ORG in Jerry’s memory.
The family of Jerome “Jerry” Harold Gemskie is being cared for by: CONRAD AND THOMPSON FUNERAL HOME AND CREMATION SERVICES, 511 Emmett Street, Kissimmee, Florida 34741; 407-847-3188.