Artist Carlo Beninati

A commercial artist for Fortune 500 companies early in his career, Carlo Beninati emerged as the go-to portrait painter of the previous century’s sports legends.

While some may experience an occasional “brush with greatness” in their lives, artist Carlo Beninati has spent a lifetime “brushing greatness,” creating portraits of the legendary sports figures of the 20th century. Joe DiMaggio, Ted Williams, Mario Andretti, Muhammad Ali, Joe Montana, Walter Payton, Michael Jordan, Tiger Woods and Derrick Jeter are among the countless luminaries Beninati has captured on canvas. Using bold colors and impressionistic backgrounds, Beninati depicts the prowess and charisma of his subjects in ways that no photograph could.

His portraits of individual legends have garnered him international renown, but Beninati is perhaps best known in the Italian-American community for a collage assembling a pantheon of greats who trace their roots to the Boot.

Commissioned by the National Italian American Sports Hall of Fame, Beninati combined the likenesses of Joe DiMaggio, Vince Lombardi, Willie Mosconi, Yogi Berra, Mario Andretti, Eddie Arcaro, Rocky Marciano and others, both posed and participating in the sports that made them famous.

Beninati’s trajectory is all the more impressive given its humble origins. While many artists develop their skills at prestigious art schools or with the support of wealthy patrons, Beninati built a career on raw talent, diligence and the patronage of the Italian-American community.

“I was born in Humboldt Park, but our family moved to Elmwood Park before I was a teenager,” he says from his home in Geneva, Illinois. “I attended Elmwood Park High School where I was part of the first graduating class. I played football on the offensive and defensive ends of the team. That and playing baseball is what probably began my lifelong love of sports. As for art, my teachers always told me I was very good, which is probably why I continued to increase the time I spent drawing.”

Beninati set his sights on being an architect while continuing to hone his artistic craft. His first break came while he was dining at Armand’s Restaurant in Elmwood Park. Beninati’s parents mentioned to owners Mike Caringella and Armand Christopher that their son was an artist. After seeing his work, the restaurateurs agreed to display his paintings in the restaurant, where they promptly sold out. Caringella and Christopher touted Beninati’s talents on the national level, convincing UNICO to commission him to paint their Man of the Year portrait in 1962.

“Mike and Armand knew a lot of influential people, and they were very kind in promoting me and my work,” Beninati says. “They set up an interview for me at a top downtown art studio: Stevens, Biondi and De Cicco. That brought me to another level.”

Beninati began to work for Chicago’s major ad agencies on projects for Fortune 500 companies. This led to him rubbing elbows with government officials, business executives, entertainment personalities and sports stars. Two of the latter were Joe DiMaggio and Ted Williams.

Beninati has done several portraits of DiMaggio, which like many of his works are reproduced and often sold at sports memorabilia conventions and auctions. “At first, DiMaggio was a bit distant, and as a celebrity, he was always very guarded,” Beninati recalls. “It was all business. He would set up his pens, put a pad down for his elbow, sign the works and give them to a notary nearby. It took a while before he began to trust me.”

His portraits of DiMaggio were seen by archrival Williams, and Beninati ended up doing similar portraits for the “Splendid Splinter.”

“With Williams, it was different,” he says. “I bonded with him, and he invited me to his home in Florida for a week where I had a marvelous time.”

Beninati’s reach was dramatically extended through his long association with the National Italian American Sports Hall of Fame.

“I was the beneficiary of a lot of effort by (NIASHF founder) George Randazzo,” he says. “Through him, there were invitations to fundraisers for the Better Boys Foundation, Athletes in Action and other groups, which is how I met Joe Montana, Dan Marino and Anthony Munoz, and eventually painted their portraits.”

Beninati’s portrayal of Montana is truly iconic. Attired in his bold scarlet and gold 49ers jersey, the football superstar stares intently down the field. By blurring out the crowd behind Montana, the artist highlights his intense concentration, almost looking into Montana’s soul. Like many of Beninati’s works, the original image was taken from a photograph, but Beninati’s interpretation transcends a merely realistic depiction.

Another notable subject was Mario Andretti, whose wavy brown hair, tough guy smile and gleaming Formula One race car are captured in the corner of Beninati’s collage of Italian-American legends.

“People forget what a big star Andretti was,” Beninati says. “His and Andy Granatelli’s STP stickers were in practically every filling station in the country.”

Beninati emerged as the go-to guy when a portrait of a sports great needed painting. Mickey Mantle, Mike Ditka, Willie Mays, Dennis Rodman and Tiger Woods were among the luminaries, but the biggest of them all may have been Michael Jordan.

“I worked a lot with Michael Jordan during the 1990s,” Beninati says. “Like almost all of the subjects, he was extremely gracious and kind. But he was such a sought-after star at that time, almost like The Beatles, that his mother handled a lot of his day-to-day business. She was also a wonderful person.”

Beninati has served as a director of the Village Art School in Skokie and member of the Graphic Design Advisory Board at Elgin Community College, as well as on the board of directors of the National Italian American Sports Hall of Fame and the Ways and Means Committee for Scalabrini Village. He and his wife of 40 years, Diane, each have three children and numerous grandchildren. In 1992, he was honored as Man of the Year by the Chicago Chapter of the National Italian American Sports Hall of Fame.

Beninati’s work has continued into the new millennium. In 2004, he was commissioned to create a poster for NASCAR’s Brickyard 400 and ended up painting portraits of drivers Mark Martin and Dale Earnhardt Sr. Extending his string of portraits of Yankees legends, he was also called upon by representatives of Derrick Jeter and Alex Rodriguez to set their images to canvas. In so doing, he has captured three generations of American sports heroes with his brush and pallet, creating images that will long outlast their on-field careers.

“I have been very fortunate to have been promoted and believed in by many important and influential people, and then to work with all these legends of sports and industry,” Beninati says. “They have always been very kind and gracious. I’m a lucky man.”

The above appears in the December 2022 issue of the print version of Fra Noi. Our gorgeous, monthly magazine contains a veritable feast of news and views, profiles and features, entertainment and culture. To subscribe, click here.