Jason Quest, 47, of Winter Park, Florida, passed away peacefully after a courageous battle with cancer, surrounded by the love of his family.

He was born in Avon, Ohio and moved to Orlando as a baby. Jason built a life defined by intelligence, determination, creativity, and strong opinions—most of which turned out to be correct. He shared a lifelong love story with his wife, Cassie Quest, his high school sweetheart, whom he met in the school band. What started as young love became a strong partnership that grew from loyalty, humor, and a shared willingness to take on whatever came next. Cassie stood by his side through everyday ups and downs, major life changes, and everything in between, and during his illness she cared for him with strength and compassion and held his hand until the very end.

Jason is also survived by his mother, Catherine (Brion) Reilly; his father, Hal (Lori) Quest; and his sister, Amy (Glenn) Stowe, with whom he shared a special bond—including the rare distinction of sharing the same birthday. As a kid he was “Ok with” the idea of sharing this special day with his new sibling, as long as her special day did not directly precede his.

Jason will be remembered for his sharp intellect and ability to solve complex problems with clarity and precision. Early in his career at Lockheed Martin, he was described as having an “abrasive personality”—a label he didn’t exactly dispute, but instead took as a challenge. Over time, and especially after founding his own company, he evolved into someone who could balance that directness with genuine connection. He became a sort of people person—but never lost the edge. In fact, that edge is what made people trust him. If Jason gave you his opinion, you knew it was honest, well thought out, and probably right.

Outside of work, Jason pursued his interests with focus and enthusiasm. Golf became a full-fledged passion, with early mornings spent at the Winter Park 9 Golf Course and an epic guys trip to Scotland in 2024 that absolutely lived up to expectations.

A lifelong bowler, Jason started young and continued through his years at Florida State University and into competitive leagues at Aloma Bowl. A semi-pro level player, he achieved multiple perfect 300 games and completed a perfect 900 series—an accomplishment that required not just skill, but patience and consistency, both of which he had in abundance when it mattered.

Jason also had a deep appreciation for cars and driving. He attended Daytona races with his father, had the opportunity to drive at Road Atlanta, and was the fastest on the course at the Porsche Experience. Over the years he owned various cars that were special to him and that he put a lot of work into: starting with the racing-striped CRX-treme, (complete with the loudest sound system in the neighborhood that let you know he was approaching your house), fast and fancy BMWs, all the way up to his most recent purchase of a unique style of Porsche 911, his ultimate dream car.

Jason and Cassie shared a life full of travel and experiences. They took trips all over the United States and around the world, including Ireland, Costa Rica, Japan, Brazil, Spain, England, the Netherlands, Belgium, Canada, and Mexico. Many of these were memorable family trips, while others were centered around concerts and experiences they didn’t want to miss. An annual trip to California—wine country paired with a music festival alongside close friends—became a tradition and one of the highlights of each year.

While Jason naturally preferred control and predictability, Cassie had a way of pulling him into adventure—and he was always willing to go along for her. Together, they explored Yosemite National Park, took on the challenge of hiking Half Dome, navigated the less-than-forgiving conditions of Mount Washington, zip-lining the canopy in Costa Rica, and a recent scuba diving adventure (with an unexpected funny twist) that added to their growing list of stories. He may not have suggested all of these experiences himself, but he showed up for every one of them.

Pets were always the core of Jason and Cassie’s home life. His first cat, Max, set the tone as an undeniably cool presence, and many others followed as Jason helped raise and foster numerous kittens in need, many of which you readers probably have adopted from us. Their dog, Lily, was a very special friend for Jason. She joined them on trips and outings and was a super sweet, loving companion.

Jason remained a loyal Florida State Seminole—even after Cassie made him live in Gainesville for four years—and he also enjoyed attending and following Orlando Magic games. He wasn’t afraid to try something new, going through a beer brewing phase and even a painting phase along the way. Nothing was ever really off the table for Jason.

Most of all Jason enjoyed time with friends, especially when it involved humor and quick back-and-forth exchanges. He had a sharp wit, a dry delivery, and an ability to land a comment at exactly the right moment. His laugh is fondly remembered by many who loved him. His laughter could fill a room, and it was impossible not to join in with him when he started. He liked to try to see who could be the funniest in the room. (Usually it was him, or him stealing Cassie’s jokes but landing a better delivery.) Beyond all the jokes, though, Jason was also always ready to offer advice and a listening ear. He did not meet many people that did not become close friends.

He was also a thoughtful and deliberate gift giver, putting real effort into finding the perfect gift—and then usually giving it early because waiting didn’t make sense.

Above all, Jason will be remembered as a devoted husband, a loving son, brother and uncle, and a fiercely loyal friend. He lived with intention, spoke with honesty, and left a lasting impression on everyone who knew him.

Jason’s celebration of life will be held May 2, 2026, from 2:00 to 5:00 PM at the Winter Park Country Club, at the Winter Park 9 course. He has been laid to rest at Palm Cemetery overlooking hole 4 of WP9—he’ll always be watching your shots.

Jason’s life ended far too soon, and we are left without his words of wisdom and insight in this moment. But those who knew him can imagine what he would say: keep having fun, pursue what matters, and stay focused on what’s important. Work hard. Play hard.

He will be deeply missed and forever remembered.