Bob Woolf

Portland, Maine

Sports Attorney

“A winner never quits, and a quitter never wins.” These words, posted at the Boys & Girls Clubs of Greater Portland, made a profound impression on Club member Bob Woolf, who went on to become America’s foremost sports attorney. He learned about competition, camaraderie and fair play at the Club – qualities that served him well throughout his career. Beginning in 1964, when Red Sox pitcher Earl Wilson hired him as counsel in a legal dispute, Woolf worked with more than 500 athletes and was named one of the “100 Most Powerful People in Sports” by The Sporting News.