Jack considers himself a native Floridian and is a proud alumnus of The Villages Charter School, with deep roots in the community. He moved to the area at just five years old, and some of his fondest memories are of summers spent with his grandparents in the Village of Springdale. Growing up in The Villages and graduating from The Villages High School instilled in Jack the core values of the community, along with a strong sense of pride in calling it home.

Jack’s parents, Randy and Karen, served The Villages from 2004 to 2016 as owners and operators of Glenview and Mallory Hill Country Clubs before retiring and becoming Villagers themselves. Their work ethic, dedication, and commitment to excellence set a powerful example for Jack and shaped his approach to serving others. His mother, Karen, now a Sales Representative with Properties of The Villages, played a major role in inspiring Jack to join the team.

After graduating from VHS, Jack attended Stetson University, where he studied Business Systems and Analytics and was a member of the baseball team. He served as a starting pitcher and team captain before being drafted into Major League Baseball by the Philadelphia Phillies following his junior season. Jack played professionally for five seasons (2018 – 2022), reaching the Triple-A level with the Lehigh Valley IronPigs before retiring just prior to the 2023 season.

Jack cherishes time with his wife Kylie, also a VHS graduate, and their son, Hudson, who was born in early 2023. As a family, they enjoy spending time with friends and loved ones, creating memories that will last a lifetime. Naturally competitive, they love watching football and baseball, playing cornhole or pickleball, and tossing a ball around the backyard. Jack, Kylie, and Hudson live in the Middleton family neighborhood, which they have proudly called home since 2024.

As a Sales Representative with Properties of The Villages, Jack is thrilled to share the community he loves with everyone he meets and looks forward to helping others find a place to call home in this remarkable area.