Jonathan Duke Kassolis

Jonathan Duke Kassolis, 42, of Naples, Florida, passed away unexpectedly on October 15, 2026. He was a devoted husband and father, a loving son and brother, and a man whose kindness reached everyone he met.

Jon was born on August 19, 1984, in Baltimore, Maryland, to Duke and Jane Kassolis. He loved his mom and dad with all his heart. They cheered him on, guided him, and loved him through every season of his life, and he never stopped looking to them as his guiding light.

He grew up alongside his sister, Kristina, and their bond only grew stronger over the years. Jon treasured his time with Kristina and her family.

Jon graduated from St. Paul’s School, where he made lifelong friends. He went on to earn his bachelor’s degree in political science from Dickinson College, his law degree from Nova Southeastern University, and a Master of Laws in Taxation from the University of Baltimore. He began his career practicing tax law at DLA Piper, the Internal Revenue Service, and RSM McGladrey.

In 2012, Jon joined Consolidated Cleaners, a Tide Cleaners franchise, as Chief Financial Officer and Legal Counsel. He was there before the first store opened its doors and helped shape the company from the ground up. Over the years he also served as CFO and General Counsel of Three60 Holdings, President and CEO of SK Holdings Real Estate, and Executive Vice President of Oxford Capital Partners. He served two terms on the Tide Cleaners Franchise Advisory Council and was a member of its Brand Advisory Group. Colleagues knew him for his sharp mind, quick wit, competitiveness, relentless work ethic, and deep passion for everything he took on. Most of all, Jon truly valued the people he worked with, and they felt his sincerity and care every day.

Jon loved soccer, cricket, and Formula 1, and he followed all three closely. Wayne Rooney was his all-time favorite soccer player. He could recall names, statistics, and results from each sport with a memory few could match.

The center of Jon’s life was his family. He and Tiffany had just celebrated their tenth wedding anniversary, and she was the love of his life. He was a loving, hands-on father to Ella, Kate, and Cole, and his greatest joy was time spent with them.

In Jon’s words: “My mission is to leave future generations of my family not only with financial security, but with knowledge, drive, and ambition to surpass the generation before them. I want them to carry forward the hunger and fire that are absolutely essential to succeed.”

Jon will be remembered for his big, generous heart. He never met a stranger, and he made everyone feel seen and valued. If someone needed help, Jon was the first to show up. All whose lives he touched felt lucky to know him, and he will be dearly missed.

Jon is survived by his beloved wife, Tiffany; their children, Ella, Kate, and Cole; his parents, Duke and Jane Kassolis; his sister, Kristina O’Keefe (Ryan), and their children, Kennedy, Clarke, and Harper; his parents-in-law, Kevin and Kelli; his sister-in-law, Kristina (Ron), and their children, Christopher, Liam, and Carter; his brother-in-law, Kyle (Daniela), and their children, Ruben and Leandro; and aunts, uncles, cousins, and dear friends on both sides of the family.

The family will hold a private burial and plans to hold a celebration of Jon’s life in the next few months.