Oswald Frederick “Trevor” Roper—known to many as simply “Oz”—was a lifelong entertainer, whether it was teaching kids to swim over two decades at the Evanston YWCA or performing around the world in the Jamaican reggae band Chalice.
“He was an entertainer of the highest quality,” says Mary Miller, a longtime friend. “Even until his last days a week ago, if a visitor would pop into the hospital he would become an entertainer and do his very best to engage them in that way.”
Roper was a swim coach at the YWCA Evanston/NorthShore for nearly two decades, touching the lives of thousands of children through the YWCA’s ‘Flying Fish’ program.
“He used that naturally entertaining personality to motivate them and engage with them, and that brought him great joy,” Miller says.
Throughout his life, music and swimming were Roper’s greatest passions, friends say. His interest in both began early in life.
In a brief autobiography written with YWCA communications director Julie McBratney, Roper said that he was born in Kingston, Jamaica, and learned to swim when he was very young.
“In Jamaica, swimming was a prerequisite for life,” he wrote. Those kids who could afford it took swimming lessons, while others learned from family members on the beach.
Jamaican Reggae Star
Roper attended college in Jamaica, and worked for Jamaica’s ministry of health and school of physical therapy for some time afterward. He decided to pursue his passion for music, in 1980, when he and some friends formed a reggae band called Chalice. The group recorded several hit singles in Jamaica and toured all over the world.
“They were spreading reggae music at about the same time that Bob Marley was,” Miller says. “They knew Bob and they played with Bob.”
As lead singer and guitarist for Chalice, Roper opened for famous acts like The Commodores and The Spinners. In his autobiography, he wrote that his last show with the band was performed in the Cayman Islands on New Year’s Eve in 1992, with Vanilla Ice and Laura Branigan.
“On January 1, 1993, I flew to Chicago,” he wrote. “I knew there was a good music scene here and I was tired of living on the road.”
About six months later, he took a part-time job teaching swimming with the YWCA. While Roper continued to play in clubs in Chicago early on and later performed privately for friends, he stayed with the YWCA for the next 19 years until his death on Jan. 1, 2013.
Natural Swim Teacher
YWCA aquatic director Pete Caragher, who hired Roper, described him as a fun-loving man with a great sense of humor. Roper worked with kids of all ages, but Caragher says he preferred to work with the youngest kids in the program.
“He could have quite easily got back into the music scene and not have to struggle doing this,” says Caragher. “He was just committed to the kids and the program here.”
Roper’s ability to entertain made him a natural as a swim teacher, Miller says. He called the kids nicknames like “earthworm” or “chicken wing,” and sometimes threw them in the water as a joke.
“Even the most reticent children, those who would walk in there and look at the pool and be afraid and cry and sit on the edge, he was able to cajole and motivate and entice them to engage with the water,” says Miller.
Roper was diagnosed with prostate cancer eight years ago, according to Miller. He underwent treatment and was able to work with little interruption for five or six years. But the last year of his life was particularly difficult. Roper had surgery in January, and was supposed to be able to come back to work in six weeks, according to Caragher. But he wasn’t able to return until May, four to five months after the surgery.
In the fall, Roper found out that the cancer had spread.
“At that point, we realized it was just a matter of time,” Caragher said. “It was a matter of controlling the pain and staying comfortable.”
On Thanksgiving, roughly 30 YWCA swim program alumni gathered for a day of relays in tribute to Roper, an event he was able to attend. The following day, several alumni of the program who are now in high school or college made a video for Roper. They played songs that he had sung with Chalice in a mock battle of the bands.
Although Roper stopped working at the YWCA during the last few months of his life, it was evident that the job meant a lot to him, Caragher said.
“Some days he had hard days, some days he didn’t,” he says. “I know he always felt better when he was in the water, working with the kids.”
In his autobiography, Roper said that teaching kids to swim had a larger purpose for him.
“In Jamaica, everyone learned to swim,” he wrote. “In the U.S., there is a history of exclusion that keeps many African American children from the water. I find this so sad, because we live beside a lake that could be as much fun as the beaches in Jamaica, but you don’t see many African American families at the beach.”
Working with the YWCA Flying Fish program, Roper believed he was helping to change that, and said he could see results already.
“I get so much satisfaction out of helping kids build morale and emerge as winners, not necessarily by winning races but by setting goals for themselves and accomplishing them,” he wrote.
It was obvious that Roper had an impact on the hundreds of kids who knew him, says Miller. As he walked in the Evanston Fourth of July parade every year to represent the Flying Fish program, you’d hear people calling of all ages, “Oswald,” and “Hey Oz,” she says. He even told her that he couldn’t go to the beach in Evanston because the kids would rush him.
“Everyone loved him,” she says.
It wasn’t just kids whom Roper taught to swim. He also gave private lessons and taught water aerobics to a loyal following of women at the Michigan Shores Club in Wilmette, whom friends jokingly called “his girlfriends.”
“His joy and his ability to entertain and motivate has reached ages in the water from the tiniest of baby and the tots learn to swim little guy all the way up to the ladies at the Michigan Shores Club,” says Miller. “They adored him.”
When he wasn’t teaching swimming or playing music, Roper enjoyed cooking Jamaican food from vegetables harvested in the YWCA community garden, according to Miller. He kept an aquarium of tropical fish in his Skokie apartment, and traveled back to Jamaica often to visit family members. He leaves behind six children.