Late Bloomer

At 13, Corrado Cirillo, now an associate at Sheboygan-based law firm Olsen Kloet Gunderson & Conway, was told he had the demeanor of a lawyer by a cook at one of his father’s restaurants. In the U.S. Army during the early 1980s, men from his platoon asked for his advice, feeling he had some unique “logical sense.”

It was high school that wasn’t so kind. Cirillo, pleading academic laziness, had a 2.1 GPA. “I always wanted to go to college, and [law school] was something I always wanted to do, but I didn’t think I had the brains for it,” Cirillo says. “My teachers in high school told me I didn’t have enough wherewithals.”

Cirillo’s decision to enter the military was both pragmatic and idealistic. His family came from Monasterace, Italy, and his parents opened five successful Italian restaurants in Wisconsin—including the Cirillo Supper Club and the Caradaro Club. They’d always told him America had been good to them. Like many immigrants, Cirillo joined the army as a way of repaying the favor.

“When you’re young, you’re idealistic,” Cirillo says. “I joined the Army for the idealistic reasons of paying back the country, finding adventure and excitement, and for the great opportunity of heroism.”

Cirillo’s idealism took a beating from the tough military lifestyle but the experience helped him get serious about his future. He took a few college courses and got A’s and B’s. After the military, to put himself through the University of Wisconsin-Milwaukee, he bartended and managed restaurants and bars. He graduated magna cum laude. Eventually he received his J.D. from Chicago-Kent College of Law in 2001.

Cirillo, now specializing in construction litigation, personal injury and insurance law, feels this long road to the law equipped him with essential skills for lawyering. “Being a person that spent time in management, I have insight as to how businesses operate and what they’re looking for in their attorney,” he says.

He adds: “My biggest accomplishment is when I get the everyday layperson asking a legal question, and being able to provide them with sound advice. It’s satisfying to help anyone who needs it.”