Developer of Wesley Chapel’s Saddlebrook, home to top tennis players, dies

WESLEY CHAPEL — As a Cleveland teenager, Tom Dempsey never could beat two neighborhood rivals in a mile race, but blamed his personality rather than athleticism.

He’d sprint the entire way and have the lead for three laps, while the others paced themselves and overtook a tiring Dempsey in the homestretch.

Perhaps he could have paced himself too, but he refused.

“I ran that way … because I do not believe in pace,” Dempsey wrote in his memoir. “I believe in attacking everything with all of my energy.”

That attitude, Dempsey would say, is how he rose from an impoverished Depression-era kid to developer of Wesley Chapel’s 480-acre Saddlebrook Resorts, which turned an area known for cow pastures into a vacationing oasis and training center for No. 1-ranked tennis players: Jennifer Capriati, Pete Sampras, Jim Courier, Martina Hingis and Andy Roddick.

Dempsey, whom friends and family called TD, died Friday. He was 97.

“TD led a legendary life,” grandson Masterson Dempsey said. “As family members, fortunately, we were beside him and witnessed his dreams actually happen.”

Added friend Sal Paolantonio of ESPN: “Tom Dempsey had the vision to build something truly unique at Saddlebrook. … I’ve traveled all over the world in the U.S. Navy and now for ESPN — and I can tell you Tom Dempsey was one of a kind.”

But nothing was more important to Dempsey than family, whom he never turned down for emotional or financial support, helping members to buy homes, pay for college and get jobs.

“We were all witness of his many accomplishments,” friend Tom Pepin said, “but his passion for family … shined the brightest.”

Dempsey inherited that desire to care for family. During the Great Depression, his father, second in command at a Cleveland steel mill, purchased a home where his wife, two sons and another eight family members lived.

“His income could then be used as the base needed for the rest of the family to survive,” Dempsey wrote.

Sharing a last name with former heavyweight boxing champion Jack Dempsey developed his toughness.

“Everyone wanted to fight me so they could boast that they defeated a Dempsey, even if I was not the Dempsey or related to him in any way,” Dempsey wrote, adding that he never lost a fight.

Serving in the Navy during World War II, Dempsey was then part of a top-secret program deploying radar, a new wartime technology at the time.

“It is not just a weapon,” he wrote. “It is a game-changing weapon” that allowed the United States to down enemy planes, boats and submarines with greater ease.

After the war, Dempsey was a top salesperson of new welding technologies for a company whose clients included the Steinbrenner family, owners of a Cleveland shipping business. He later ran Industrial Publishing, which printed trade publications, and negotiated the company’s merger with Pittway Corp., for which he eventually became chairperson.

It was through Pittway that Dempsey built Saddlebrook. Originally envisioned as a country club by PGA golfer Dean Refram, Dempsey had Pittway take it over in 1979 when construction stalled due to finances.

Dempsey rebranded it as a timeshare of sorts where owners of the 500 condominiums could stay for a limited time per year with management then renting the units to tourists who had access to resort amenities, two golf courses designed by Arnold Palmer, and 43 tennis courts that include all four Grand Slam surfaces.

He purchased Saddlebrook from Pittway in 1988 and moved to Wesley Chapel full time.

Saddlebrook is perhaps best known as home to the Harry Hopman Tennis Academy, which Dempsey brought there to train tennis players. Courier and Sampras rose to No. 1 in the world after moving to Saddlebrook; Hingis returned to the top position after doing so; and Capriati and Roddick became teenage sensations while residents.

All the while, Saddlebrook operated as a family business.

“TD blended family life and business naturally,” granddaughter Alexis Doyle said. “His business was his family, and his family was his business.”

Wife Eleanor Dempsey, who died in 2017, operated the resort’s stores. Daughters Maureen Dempsey and Diane Riehle served as his right hands. And five grandchildren worked in a variety of positions.

“My favorite thing he said to describe his accomplishments was, ‘I’m having fun doing what I’m doing all my life,’” grandchildren Thomas, Robert and Lauren Riehle said in a joint statement. “His motivation was providing for and protecting the ones he loved.”

Added daughter Riehle: “I watched my father build a very successful career in Cleveland as I grew up. The constant in each of these chapters is that my dad held his family as his rudimentary building block in every aspect. TD got us all involved.”

In 2022, Dempsey sold Saddlebrook to Mast Capital, a Miami real estate investor, but did not slow down. He continued to invest in businesses, including health clinics and restaurants.

“Life is too short for pacing,” he wrote as the conclusion to his memoir. “Sprint the whole way dammit. Never slow down. Never forget family. Do not live with regret.”

Service for Tom Dempsey

The visitation will be on Thursday, March 21 at 7 p.m. at Blount & Curry Carrollwood, 3207 W. Bearss Ave.

The funeral will be on Friday, March 22 at 10 a.m. at Saint Leo Abbey, 33601 County Road 52, Saint Leo. It will be followed by a celebration of life at noon at the Royal Palm Ballroom at Saddlebrook Resort, 5700 Saddlebrook Way, Wesley Chapel.