Politics & Government

Ben McCready x’76

Portrait Painter


Andy Manis

Nancy Reagan was not impressed by any of the portraits that had been painted of her husband. When the president of the United States needed a new one for his library, she had two conditions for the artist: no money up front and no in-person meeting.

Ben McCready x’76 of DeForest, Wisconsin, agreed and, working from a photo, delivered a three-quarter-length portrait of a smiling Ronald Reagan wearing a dark brown suit. The First Lady was delighted. “She called and said, ‘You made him look so alert and so kind,’ ” McCready recalls. Others, she added, had made her husband seem dull.

The ability to produce representations that are both genuine and flattering has afforded McCready a career that’s included painting portraits of four U.S. presidents; hundreds of corporate executives and university leaders, including 11 from UW–Madison; and several celebrities, such as George Clooney and Paul Newman.

After college, McCready sold insurance, worked in politics, and was an executive recruiter. In 1982, he decided to pursue a career as an artist. Although he had taken just one art course at the UW, his education had started much earlier: both of his parents were trained artists.

McCready’s first portraits were for friends and family, painted for free or next to nothing. After sending samples of his work to hockey star Wayne Gretzky and actor Robert Redford, both commissioned portraits. Redford allowed him to use the work freely for publicity, which increased McCready’s clientele.

At his peak, McCready painted 20 portraits a year. Despite receiving more than 100 requests annually, he now paints one a month — often hopping on a plane to meet with the subject and take photos — and his schedule is filled for the next year and a half.

The lessons that McCready learned during his time selling insurance proved invaluable in his career as an artist. “You’ve got to sell yourself,” he says. “You can have the most incredible skills, but if you can’t sell, it might be hard to sustain your career.”

The wisdom that McCready gained about self-discipline and time management while at UW–Madison has also been critical. “I just loved my classes, the academic life, the social life at Wisconsin,” he says. “It was so challenging academically that you got a lot of confidence when you did well.”

Published in the Fall 2016 issue


  • Rob Dautermann March 8, 2024

    I knew this man when I was a child. He was my soccer and baseball coach in the early 80s, when he was getting his career off. We painted houses together for a few summers as well. He was like a caring older brother who always made time to enrich the lives of others.

    His first portraits were amazing to see. He lived in Lake Geneva and had a studio in his home with multiple portraits at various stages. He was meticulous about details. I recall being in the room with the Wayne Gretzky, Gerald Ford, Ronald Reagan, and Donald Trump (pre-politics) portraits.

    Ben was an incredibly positive force in my life during some very formative years. After he started his family, we drifted apart and ultimately lost contact. I would check in on him occasionally electronically.

    Speaking of him with my wife a few minutes ago, I decided to check up on him. It saddens me to learn of his passing, but I know he led a life of service, sharing love with everyone he encountered. I have admired him for the last 40+ years. Such a good person and his talent was and will be unparalleled.

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