Trueman's early entrepreneurial interests included Deibel's, a German-style restaurant in Columbus, Ohio. In 1972 he opened his first Red Roof Inn motel, and the chain grew rapidly: by 1986 it comprised at least 155 properties, making Trueman a wealthy man. He also owned Mid-Ohio Sports Car Course near Lexington, Ohio, purchasing it on October 1, 1981 and immediately investing in improvements to the facility. Under his ownership Mid-Ohio became one of the most respected road circuits in the United States, hosting CART, IMSA, Grand-Am, IROC, SCCA, and motorcycle events alongside vintage racing weekends.
Trueman began driving sports cars in 1962 and competed through the 1970s, participating in the Can-Am series among other competitions. Over 23 years he won 125 races and earned SCCA national championships in 1975 and 1978, establishing genuine credentials as a racer before transitioning to team ownership.
Using revenue from the Red Roof Inn chain, Trueman expanded into sponsorship and team ownership. He first backed Vern Schuppan at the 1981 Indianapolis 500 under the Red Roof Inns banner; Schuppan finished a strong third. In 1982 Trueman shifted his focus from Can-Am to CART, forming what became the Truesports operation and finding immediate success.
Bobby Rahal became the central figure in the Truesports effort, and the pairing built steadily toward the top of the CART field. By 1986 the team was a genuine Indianapolis 500 contender.
In 1985 Trueman was diagnosed with cancer. He kept his illness private for many months while continuing to run the team. By the time the 1986 Indianapolis 500 arrived, he was visibly frail but insisted on spending the entire month of May at the Speedway. The race had been scheduled for May 25, his 51st birthday, but rain postponed it; Rahal's car carried a "Happy Birthday JRT" decal in his honor. The race was finally run on Saturday, May 31.
With two laps remaining, Rahal passed Kevin Cogan on a restart and held on to win. In victory lane, an emotional Rahal was nearly overcome. Trueman stood to accept the traditional bottle of milk. ABC television reporter Jack Arute later revealed that Trueman whispered to him: "I can go now."
Five days after the victory, on June 5, the city of Columbus held a downtown parade to celebrate the win. Trueman was too ill to attend. On June 11, 1986, eleven days after the race, he died at age 51.
The rookie of the year award in CART was named in Trueman's honor, recognizing his contribution to the series. Mid-Ohio Sports Car Course continued to grow as one of North America's premier road racing venues in part because of the infrastructure investments he made during his ownership.
His family connections extended into the next generation of American motorsport: his daughter Megan married Tim Cindric, who became president of Team Penske and one of IndyCar's most respected strategists. Their son Austin Cindric, Trueman's grandson, became a driver in NASCAR, born twelve years after his grandfather's death.
Trueman's story — a self-made businessman who loved racing, who built a championship team and lived just long enough to see his driver win the biggest race in America — remains one of the most poignant in the history of Indianapolis 500.