James Joseph "JJ" Jennings
April 14, 1946 – March 25, 2025

Our father, James Joseph "JJ" Jennings, 78, passed away on March 25, 2025, in Clermont, Florida. Throughout his life, he was affectionately known as Jimmy-Joe, Jim, and JJ.

Born on April 14, 1946, in Saegertown, Pennsylvania, to Marie Elizabeth (Callahan) and Lloyd "Frenchie" Jennings, JJ was loved for his magnetic personality, gift for storytelling, and boundless enthusiasm for life. A gifted athlete, he excelled in both golf and football during his years at Saegertown High School, graduating with the Class of 1964. With his easy charm and genuine interest in others, he found his calling on the road as a successful traveling salesman—a path that would change his life forever.

While on the road, JJ met a co-worker who would become the love of his life—Darlene Hengst. Their connection was instant, and they eloped in Texas, beginning a journey full of love and adventure. After spending a few years in their home state of Pennsylvania raising their young family, they sought a warmer climate in Orlando, Florida, in the early 1970s. There, JJ found success in life insurance sales, but it was his entrepreneurial spirit and passion for golf that led him to open a golf and tennis store. Eventually, JJ discovered his true calling in real estate, just as Disney began building its parks and Orlando's growth surged. As the city expanded, so did the opportunities in both residential and commercial real estate, and JJ thrived in this burgeoning market.

In 1985, JJ's world was shattered when he lost Darlene. Despite the overwhelming grief, he rose to the challenge of raising two teenagers with strength and determination. Then, as life often does, love found him again in Cindi Gary. They married in 2002, blending their families with Cindi's son, Jason, and his daughter, Lindsay, into their lives. JJ and Cindi built their dream home in Green Valley Country Club, in Clermont, Florida, and boy, did they know how to throw a party! Their home was always filled with laughter, good food, and great company. Those who attended their gatherings still talk about them today.

Tragically, a decade into their marriage, Cindi suffered a debilitating stroke that left her wheelchair-bound. Without hesitation, JJ stepped away from his lucrative career to become her full-time caregiver, a true testament to the depth of his love for her. During the next 12 years, as he devoted himself to her care, JJ discovered a new passion—collecting. What began as a simple hobby soon evolved into a business specializing in retired McDonald's Happy Meal toys.

JJ was preceded in death by his first wife, Darlene Jennings, and his second wife, Cindi Gary Jennings. He is survived by his daughter, Teresa, and her husband, Jim LaRuffa of Pompano Beach, FL; his son, Scott, and his wife, Sharon Jennings of Margate, FL. He is also survived by his stepson, Jason, and his wife, Chloe Gary of Seattle, WA. He also leaves behind five grandchildren: Lindsay Gary Ponomarev, Mia LaRuffa, Trent LaRuffa, Holly Gary, and Timber Gary, as well as two great-grandchildren, Lucas and Leo Ponomarev.

JJ was a deeply loved great-grandfather, grandfather, father, husband, uncle, cousin, brother, and friend. His passing came too soon, but he left this world with gratitude, peacefully in his sleep.

A celebration of his life will be held at Green Valley Country Clubhouse, in Clermont, Florida on April 19th from 2-4 pm. In lieu of flowers, the family kindly requests that donations be made to JJ's memorial fund on GoFundMe, at https://gofund.me/f10dbda0

We wish to honor him by installing a meaningful memorial in his name, offering a lasting tribute of JJ at his beloved Green Valley Country Club. Golf courses have always been places where friendships are forged, stories are shared, and quiet moments of reflection are found. By contributing to this memorial, we invite both friends and strangers alike to pause, rest, and acknowledge a life well-lived.

To know JJ was to love him. He had a warmth in his heart, a joke always at the ready, and a special talent for entertaining. He could captivate both children and adults alike with his magic tricks, leaving them in awe of his sleight of hand. His sense of humor, charisma, and love for storytelling made him unforgettable. JJ had a way of making everyone feel like they belonged, and his presence will be sorely missed.

We invite all who knew him to share pictures and memories. JJ wished for laughter, reminiscing, and smiles during this time of remembrance. He wouldn't want us to dwell in sadness but to celebrate a life well-lived, full of love, adventure, and plenty of good times.