August 2025 Athlete of the Month
By Del Moon, NSGA Storyteller
Derrick Milligan, 60
Chicago, Illinois
Derrick Milligan (far right) and his teammates at the 2025 National Senior Games presented by Humana Triathlon.
On a misty, muggy morning at the 2025 National Senior Games presented by Humana, lifelong athlete and Team Dream coach Derrick Milligan watched members of the three teams he brought to Des Moines for the Triathlon Relay compete. He speaks of always being in sports and explains what drives him at age 60.
“I now consider this activity as my ‘insurance policy’,” he says purposefully.
The North Carolina native started on a swim team at six and played in his first tennis tournament and refereed basketball game at nine. He was an all-state tennis player and an all-city point guard in high school. After failing to make his varsity tennis team at Miami University of Ohio in 1984, he saw a flyer for a triathlon that weekend. “To punish myself for not being in better physical condition for the tennis match that would have put me on the varsity, I decided to do my first triathlon untrained,” he recalls.
Derrick has completed more than 120 triathlons since then. During the years he was pursuing a busy marketing career, playing tennis and doing tris was how he relieved stress and kept in shape. In 1997 he changed course and began coaching others as part of a renewed dedication to fitness. It all came home after witnessing his family’s health history.
“My two grandmothers had five heart attacks, two strokes and a pacemaker between them,” he says softly. “My father died at 61 from his first heart attack. I was already working on his lifestyle and teaching him how to swim. He really was starting to address all the corporate stress that piled up over four decades of working. So, it really bothered me that he died that way on my watch.”
That is why Derrick believes he’s taken out an insurance policy to live a longer and better life. “My mother died this year of congenital heart failure, and her kidneys were probably at 30%. Even though she lived to be 84, the last 25 years have not been high quality because of her health,” he shares.
“That’s what drives me,” he adds. “I want to be very active with my grandchildren, and I don’t have any yet, so I’ve got to keep it together.”
Team Dream Becomes a Documentary – and Regular in Senior Games
In 1999, Derrick formed Team Dream in Chicago as an organization to train women of color in swimming, cycling and triathlon. In 2015, he coached African American swimmer Ann Smith to do Triathlon and Swimming at the National Senior Games in Minneapolis. Ann then decided to focus on the pool and competed in six Swimming events in 2017, with Derrick bringing along six other Team Dream athletes. More came in 2019 and 2022.
During this time, longtime friend and filmmaker Luchina Fisher took interest in his mission and the journey of Ann Smith and her friend and fellow swimmer Madeline Murphy-Rabb in their quest to win a national medal. The result was the award-winning 2022 documentary, “Team Dream.” Read our 2022 story for details. Derrick also won a bronze medal in Tennis doubles in that year.
This year, Derrick recruited three Triathlon Relay teams for The Games in Des Moines. “Most of our history has been all-female, but we started incorporating more male activities,” he says. “Our co-ed team won gold, our all-female team won gold, and then our all-men’s team won silver.” The men’s team revealed a dramatic story of one member’s comeback from a stroke as reported in the 2025 Games Daily News.
The Team Dream teams at the National Senior Games Triathlon Relay in 2025. Photo courtesy Derrick Milligan.
The athletes enjoyed their experience, despite the unfortunate development of poor water quality that required the swim leg to be canceled. By triathlon rules, the swim segment becomes a one-mile run, which disrupted many teams.
“The biggest letdown was the swim being canceled for my three swimmers, including myself,” he says. “But since I pull people from all over the country, they loved the camaraderie, going around town, the meals and seeing everyone.” Undaunted, Derrick says he plans to bring 10 triathlon teams to the 2027 Games in Tulsa. He’s grateful for how Team Dream has progressed and intersected with Senior Games, and he has been inspired by his swimmers to double down on his insurance policy.
“I already wanted to be at a certain level of efficiency in my 70s, but Ann introduced the concept of thriving at 100 years of age, which I hadn’t really thought of,” he says. “So, I’m 60 and never had a heart attack. My blood pressure is optimum. I don’t have high cholesterol. I don’t have diabetes. All are things that run rampant in both sides of my extended family, and I don’t have them because of the lifestyle choices.
“I’m very grateful to Ann and Madeline, he concludes. “They’ve raised the bar of my already high expectations.”
