Part of the reason Roesler is so selective about whom he represents is that properly managing the affairs of his clients requires his team of lawyers to secure copyrights and trademarks for CMG’s clients all around the world, a task that has become increasingly complicated both as the economy has become more globalized and with the explosion of social media and the Internet. The complicated, ongoing and arduous legal work is just one aspect of Roesler’s responsibilities. His company also handles anywhere from 1,500 to 2,000 deals annually on behalf of its clients.

In fact, Roesler is so busy — he says his offices often start the day dealing with offers from Europe, where the business day is ending as his begins, and ends it working with Asia — that pressing negotiations delay our scheduled interview a few times. When we finally do talk, it’s on a typically frenetic day. In the morning, Roesler says he was handling an inquiry from a British clothing company called Worn By, which had gotten in touch about the possibility of featuring 1950s pinup starlet Bettie Page (another Roesler client who made the Forbes list in 2011) on a line of T-shirts. “This morning we were also finalizing a deal with Max Factor to promote their cosmetic line with Ava Gardner,” a deal Roesler says makes a lot of sense. “Associating Max Factor with Ava Gardner draws on her beauty and name recognition.”

Even though Roesler now spends his days managing the affairs of some of the world’s most famous names, he started his career simply wanting to fix roofs. In 1974, Roesler teamed up with his cousin Chuck to start a roofing company, with the idea that it would allow them both to earn enough money to pay their way through college. For the next seven years, Roesler worked every summer and weekend up on roofs that had been damaged by powerful storms or neglect, until he graduated from Indiana University with J.D. and M.B.A. degrees.

Because he graduated in December 1982, Roesler had a few months to kill before diving back into his roofing work. It was enough time for his mother — who hated the idea of him spending his career doing something where one misstep could be deadly — to convince him to explore some other, safer opportunities. Much to his mother’s relief, Roesler started working for an Indiana company called Curtis Publishing, owners of The Saturday Evening Post. Because of his legal training, Roesler was given the task of licensing the use of the Norman Rockwell illustrations the company owned — a big job considering that the nation’s 1976 bicentennial had generated enormous interest in the sort of classic Americana that Rockwell produced.

Roesler found the intellectual-property issues in his work intriguing, and he got a big break when Presley’s estate became interested in exploring ways to profitably use the then recently deceased (Presley died in 1977) singer’s name and likeness. “We discussed how we could use the expertise we had acquired in working with the ?Norman Rockwell illustrations,” recalls Roesler. “They were interested, and we decided to do various collectibles with Elvis Presley.”

To do that, Roesler and Curtis opened up a separate company — with Roesler as part owner — which Roesler soon purchased outright. Working for Presley and Rockwell, two of the most recognizable names in America, was a pretty good start. But Roesler soon realized that the legal protections for deceased celebrities were few. “There just weren’t many rights representing deceased people and their heirs,” he says. The example of Dean is illustrative of the lack of intellectual-property protections that existed in the early 1980s. At the time, for instance, Levi Strauss & Co. had a major advertising campaign in Japan called “Heroes Wear Levi’s” featuring Dean, for which the family received no financial compensation.

As much as Roesler set about building his business — quickly signing up Dean’s relatives, who live just outside of Indianapolis — he also got to work waging legal battles to affirm the rights of the heirs of deceased celebrities. “We set out to change those laws and to get people’s attention that this was something that families should control,” he says. What followed was a series of high-profile legal battles that have essentially enshrined the legal rights of the descendants of famous athletes, musicians and actors. For example, Roesler tussled with the Warner Bros. studio over the merchandising and endorsement rights associated with Dean. The studio contended that the rights were theirs because he was under contract with Warner Bros. when he died. Roesler successfully argued that the family retained those rights. Roesler also prevailed in a battle with Major League Baseball that allowed retired players to appear in the uniforms they wore during their playing days when they endorsed products. Roesler later forced movie director Spike Lee to pay a licensing fee to Betty Shabazz for the use of the letter “X” in association with his biopic Malcolm X about her late husband, Malcolm X. Roesler is more or less responsible for the passage of numerous state laws that protect the use of a celebrity’s name and likeness for up to 100 years.