Lenny Rago (left) with his son, Joey at Panino's Pizzeria in Evanston.RoundTable photo

A pizza-making teenager, an entrepreneur with a string of successful business ventures, and a famous pizza champion. Lenny Rago has been all of these things. So it is not a surprise that his pizza was recently named “Best in the Midwest” –  or that he was getting ready to head to Italy for another competition. Over the years, Mr. Rago has received many honors for his pizza, but he was excited to talk about the most recent – almost as if this were his first win.

The “Best in the Midwest” title was awarded to Mr. Rago at the Mid-America Restaurant Expo, as a part of the Expo’s annual “Pizza Pizzazz” competition. He competed against 45 other pizza-makers, and there were 30 judges involved in the double-blind judging process. They chose Mr. Rago’s “Hog Heaven” pizza, which has a pan-style crust and toppings that range from a blend of pepperoni and ground sausage, to applewood smoked bacon and barbecue sauce. He planned to use the $5,000 top prize from the contest for a trip to Italy to participate in another competition.

Talking about how he comes up with a winning pizza, he said, “I try to get a balance of flavors. I look at what’s popular on our menus and around the country.” He went on to say that he wants his competition pizza to have striking color and a unique, but balanced taste. He also pays attention to current pizza trends as he comes up with the recipe. When asked if he is concerned about sharing details that competitors might want, he explained that there is a brotherhood of pizza-makers. “We talk about what we make, we share ideas.”

Growing up in his parents’ Italian restaurant, he was drawn into pizza making at 15. During that same time, he was also learning about entrepreneurship. His father, who was in construction, would have very little work during the winters and decided that he should open an Italian restaurant.

Mr. Rago did not continue working at his parent’s restaurant, and his path forward did not lead right to pizza. There were a couple of very successful businesses in a fairly short number of years. When he was 17, he opened a car wash and detail shop, which he now refers to as “my bucket of soap.” He ran the car wash while also working for an HVAC company, and still found time to open a second car wash. He sold both for a profit when he was 19. After that Mr. Rago ran a successful DJ business, catering to parties, weddings and other events. He had his last event as a DJ on New Year’s Eve 1999 and then went to work for an Italian food-distribution company. He was only there a short while, before he and his brother Gino decided to open Panino’s.

Mr. Rago speaks warmly of opening their first restaurant, which was located on Central Street in Evanston. “It was great,” he said, “There would be these big rushes of people that would come through the doors before and after movies. The business was good.” They lost their lease on Central Street when the landlord sold the building to a developer, who demolished much of the block. Mr. Rago explained that, while they were sad to leave the location, the business kept expanding. Apart from the Evanston location on Dempster Street in Evanston Plaza, they opened a Panino’s in Chicago’s Lakeview neighborhood and in Park Ridge.

Mr. Rago believes that part of the reason they are so successful is that “Everything on the menu is homemade. We make all the pepperoni, the sausage, the sauces, the dough, everything.” He said that that is also true about Panino’s gelato. As he stood over the opened gelato cooler, spooning up samples and tasting them himself, he talked about his gelato. A woman seated nearby overheard and chimed in about her favorite flavor. He responded by giving her some sample tastes as well.

Mr. Rago said he had worked hard and put a lot of love into all of his jobs and each of the businesses he started, but that pizza-making and owning restaurants is what really makes him happy. Mr. Rago introduced his son, Joey Rago, who also works at Panino’s, and then as he put his arm around him said, “Someday this will all be his. He’s gonna run it all.”