Robert Stephen Simon: One Prolific Painter

He was a man who simply loved to paint, right until the very end. There are not many who feel they are at the peak of their game at the latest stage of their career, yet that is exactly what Robert Stephen Simon said on numerous occasions this past spring.

Simon, who suffered a massive heart attack, passed away May 29. He was 74.

Those who have been reading SCD for the past several decades can remember Simon’s ads dating back to the 1980s. His passion never wavered, nor did his portfolio of subjects, even through tough times in the art market.

Robert Stephen Simon had an affinity for the N.Y. Yankees, as witnessed by one of his later pieces, “Yankee Pride,” featuring 100 members in a single piece. However, Simon did everything – profiles, landscapes, classic cars, etc., during his lengthy career.

Robert Stephen Simon had an affinity for the N.Y. Yankees, as witnessed by one of his later pieces, “Yankee Pride,” featuring 100 members in a single piece. However, Simon did everything – profiles, landscapes, classic cars, etc., during his lengthy career.

Simon thought highly of his art, and rightfully so, and he wanted to share his work whenever possible. Sharing meant consigning to galleries, which resulted in details and dealings requiring the aid of a lawyer. Affiliating himself with attorney Craig Donoff, launching what would become a 20-year personal and professional relationship, Donoff is now executing the settlement of Simon’s estate.

“He’s a very famous guy,” Donoff said. “He’s been doing this for 50 years.”

Donoff is now in charge of the Simon’s holdings, which includes thousands of pieces of original artwork, lithographs and giclees, many signed by the athletes and celebrities he depicted.

“He didn’t have any specifics,” Donoff said of Simon. “He wants me to perpetuate his art. Hopefully it will be in a museum for his memory. He has tens of thousands of lithos we’ll have to liquidate or distribute.”

Donoff is in the early stages of the inventory work, but for now, he wants to share Simon’s legacy and work, of which he is a big fan himself. Among the pieces that amazed Donoff were “Yankee Pride,” “Simon’s Greatest of the Greats” and “Inspirations of a Lifetime,” the latter a painting of people who Simon held dear, including Mickey Mantle and Joe DiMaggio, whom he did many pieces with.

“How do you paint 100 Yankees in such a small area and everyone looks so real?” Donoff said of the “Yankee Pride” piece. “It’s amazing to see, that someone had that ability to paint and do it quickly and meticulously.”

Simon wasn’t an art student. He attended Ohio Wesleyan and received a  degree in business. He didn’t want to go into the family box business and instead became a freelance artist. His career began in the 1970s when he started painting members of the N.Y. Yankees. Aside from his original art, sports collectors have seen his work on Sports Impressions collector plates, TCMA’s Super Star baseball card set and numerous other artistic renderings.

“He was prolific,” Donoff continued. “A lot of artists are lazy. He always had a brush in his hand because he loved it. He didn’t let anything grow under his feet. He never gave up.”

Simon counted many famous people among his friends, from George Steinbrenner and Mickey Mantle to Duke basketball coach Mike Krzyzewski. His home was filled with signed pieces and personal letters from these types of folks, and Simon treasured those relationships.

“There wasn’t one wall space that didn’t have one of his oil paintings on it,” Donoff said. “Wall-to-wall paintings – and that wasn’t a warehouse, it was his house.”

Donoff said thousands of collectors have pieces of his work, and now it’s up to him to perpetuate Simon’s work and keep his name in the public eye.

“I never had an estate in over 30 years that had as many pieces of memorabilia as he has, along with letters from presidents, letters from Mantle and DiMaggio – personal letters that were sent to him that he kept. That’s all part of his collection,” Donoff said. “If I was able to put it into a museum, you’d have to have a pretty big museum.”

Those interested in obtaining pieces of Simon’s artwork or seeking to assist in housing Simon’s art in some fashion can contact Donoff’s Boca Raton, Fla., office at (561) 451-8220.

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