‘T.D.’ & His Grandkids Share A Special Milestone

Masterson and Alexis Dempsey of Wesley Chapel graduated from Saint Leo University on April 30.

Alexis received her Master of Business Administration (MBA) degree during the morning commencement ceremony, and Masterson received his Bachelor of Arts (B.A.) degree in International Tourism & Hospitality Management during the afternoon graduation exercise. Masterson, an Honors graduate, also got to deliver the farewell address to the Class of 2016.

Both are the grandchildren of Tom Dempsey, the founder, chairman and CEO of Saddlebrook Resort off S.R. 54. “T.D.” (as many in his family call him), who received an honorary Doctorate in Humane Letters from Saint Leo in 2008 and is a Trustee Emeritus — got to personally present his grandchildren with their degrees. He served on the Saint Leo Board of Trustees and was on the search committee for Dr. Arthur F. Kirk Jr., the former president of Saint Leo University.

Dempsey, who has the middle name Leo, said, “I have thoroughly enjoyed watching them grow up. Alexis is a superstar and doing a fantastic job at the resort. Masterson already has over four years of experience at Saddlebrook and is pursuing his passion for music. I am extremely proud of them both, and presenting them with their degrees, was a special moment indeed.”

Both students currently work at Saddlebrook Resort. Alexis is the Catering & Conference Services manager, and Masterson is a DJ and entertainer as well as having experience as a guest activities specialist, corporate team building facilitator, athletic event referee and fitness instructor.

When asked about the significance of the upcoming milestone, the siblings, who are 16 months apart, responded in a similar fashion: “Saint Leo has been a part of our lives since we were young,” said Alexis. “The university’s values reflect our same family values – it’s the way were raised.”

Masterson added, “The same values are infused within the staff at Saddlebrook Resort. Our grandfather did everything for our family, and this attitude is reflected in his work – his leadership, service, and support to make the business successful. T.D. is a ‘big picture’ thinker. He believes in the importance of service leadership, and we had the privilege of witnessing it firsthand.”

Masterson was an actively engaged student who served as President of both the L.E.A.D. Scholars Organization and the International Tourism Club at St. Leo. He also is a Big Brother to the Gamma Upsilon Sorority and a member of Omicron Delta Kappa National Leadership Honor Society. In addition, both he and Alexis served as peer ministers in Saint Leo Abbey’s Youth Ministry Program.

Alexis also stays busy with numerous community service activities. While earning her undergraduate degree at the University of Central Florida in Orlando, she was the recipient of a four-year merit award given to two students in each state based on exemplary community service and academic achievement. She logged more than 600 hours of community service with the Children’s Home Society of Central Florida. She is very active at her church, St. Mark the Evangelist Catholic Church, and the Junior League of Tampa Bay, where she serves as Metropolitan Ministries Food and Materials Coordinator. She recently joined the Wesley Chapel Noon Rotary Club.

While Masterson described his sister as more “polished” and himself as more “raw,” he considers his sister his “co-warrior” through life.

“Now that we’re starting our professional careers in the family business, it’s an ‘open competition’ and we intend to push each other to be the best that we can be,” he said.

T.D. wouldn’t have it any other way.