Bouncing Back

Oak Island resident Tripp Roakes turned the gift of pickleball into a bountiful Christmas toy drive.

It’s mid-November and cooler than usual on Oak Island, but Tripp Roakes isn’t feeling it. He’s been playing a 10-hour pickleball marathon on the town’s courts since 9 am, and he won’t stop until after the sun disappears over the ocean, a block away.

The Santa Slam-A-Thon behind Oak Island Town Hall was his idea, with the initial goal to raise enough money to purchase at least 500 toys for Brunswick County children. So he plays, opponent after opponent, a 10-minute break after every fifth game.

He wants to make the marathon an annual event.

“I didn’t want to get too big on this first one,” Roakes says. “I will double the size of it next year. A lot of people have brought ideas who want to help me. It’s not an attendance-type event. We aren’t playing for a championship.”

Roakes, 59, is new to pickleball, and the island.

For 31 years he lived in Charlotte, where he’s well-known in youth sports.

“I own over 30 youth sports camps and 12 large scale youth sports events in Charlotte and across North Carolina,” Roakes says. “I still run all of that but I only have to go to Charlotte about 50 nights a year.”

He oversees high school and middle school baseball and softball camps, cheerleading camps, events for football, lacrosse, track and field, baseball showcases, recognition events for student-athletes, even sports photography services.

But pickleball?

“It has changed my life,” he says, “and truly put me back in a good spot.”

Roakes’ world changed in 2021 when his wife of 21 years, Grace, was diagnosed with brain cancer, a glioblastoma tumor.

“The worst kind you can have,” he says. “She made it 21 months. Before she passed away, we came down here and bought a house because we were checking off some bucket list items, and she made it very clear to me that when she died, she wanted me to live at the beach and enjoy life.”

Through an acquaintance, a former NASCAR employee who works in local real estate, the couple found their island home.

“He made it quick and seamless, and he and his wife were the only people we knew who lived on the island,” Roakes says.

Grace Roakes, 57, passed away in March 2023.

“Part of my journey that brought me here is that this is where she wanted me to be,” Roakes says. “She was a planner, and she planned a lot of things. She wanted me to be here and live again and be the best person I could be. The very few months we had here, before her last three months, the time we had here was from September to December and we were able to go to the beach and not have everyone else there. I love walking the beach this time of year, with nobody out there. Going out there was part of my recovery. I found a lot of peace from that beach after she passed.”

Roakes moved into the couple’s new Oak Island house in August 2024 and began to further explore the area.

He had heard about Bald Head Island and met someone who took him to see it. That’s where he saw pickleball courts, like the ones behind Oak Island Town Hall on 46th street.

The game intrigued him: Tiny courts only 22-feet wide and 44-feet long, not 36-by-78 like tennis. Paddles, not rackets. No fuzzy, rubber tennis balls; players had smaller ones, made of perforated plastic.

Roakes made the move to Oak Island full time in August 2024 and began to explore all the island had to offer.

“I can’t stress enough how my life changed when I discovered pickleball. I began meeting friends. I began fitting into my community,” Roakes says. “Everything became better because of walking onto these courts.”

The Santa Slam-A-Thon was Roakes’ second event to benefit area children. For Christmas 2024, he purchased about 100 toys and worked through school system social workers and guidance counselors, who distributed his gifts. For the Santa Slam-A-Thon in 2025, Roakes connected with the Oak Island Police Department to match up families.

“Together we hosted a distribution event a few days before Christmas,” Roakes says. “I also distributed a large amount of toys to a couple of domestic violence organizations and helped a few families that I knew needed to have their Christmas brightened up.”

He tried to include a wide geographic area and all ages.

“We’re talking about Winnabow, Boiling Spring Lakes, it’s a big county. And it’s not just the younger kids. A lot of times, middle schoolers and high schoolers get left out of these kinds of things, but it’s Christmas for older kids as well.”

Roakes is quick to credit Kim Winfrey for her help with the event.

“Without her help, the entire event would have never gone as well as it did,” he says. “Kim provided me so much support and encouragement throughout the event and she helped in every way possible to make the event a big success.” By the conclusion of November’s Slam-A-Thon, Roakes had raised enough for 650 toys to be distributed in Brunswick County.

The next day, he did the math: “We had over 70 people play an hour with me during the 10-hour marathon,” he says. “I won 87 percent of the games I played on the day! I played 57 games of pickleball with 54 different partners. Took over 47,000 steps on the courts!”

His final game at 7 pm included his and Grace’s son, Tyler, who drove down from East Carolina University for the event.

Next year’s goal? Raise enough for 1,000 toys, work with area charities and hand-deliver Christmas gifts to some families, with help from the local police department.

“I am eternally grateful for how this community has welcomed me into the area in just over 15 months,” Roakes says. ‘To see so many players and others come out to the courts was very heartwarming and allowed me to understand how special living in a small town can be. I feel like I have found my place here, and I am proud to be a Brunswick County resident and to do my part in helping others.”