The Richard F. Gregory Visiting Writing Series is a program launched by Shady Side Academy Senior School in Pennsylvania last year that features authors who spend a year on campus speaking and working with students as part of the English curriculum. The small school started in 1883 in a one room building and has since grown to produce alumni including two-time Pulitzer Prize winning historian David McCullough, screenwriter Peter Ackerman, Navy Admiral Richard G. Colbert and a host of others who since made their name in environmental, financial, creative, sports, literary, music and political fields.
But the man the Series is named for was a fascinating gentleman in his own right, an English teacher at the Academy for 36 years, and a New York native who as a 12 year-old posed for Norman Rockwell’s famed illustration of Tom Sawyer.
PHOTO: Richard F. Gregory was the child model for this depiction which became a U.S. stamp.
Gregory died in 2014 at the age of 90, and was survived by a son and a daughter, as well as a sister and grandchildren. His daughter is Christine Gregory of Freehold, an activist like her dad, and a woman interested in her community and her country. Christine laughs when she proudly announces she can stand up against any man or any other force that tries to quell her spirit, given her growing up years surrounded by Academy students, at the time, an all-male school.
The senior Gregory was known on campus as the “implacable guardian of the written word” was also an athlete, lettering at Manhattan College in baseball, golf and swimming, setting records and captaining the swim squad and honorary captain of the golf team. At Shady Side, he was also tennis coach and beloved both as a teacher and a coach.
It was when he was a youngsters living with his family in New Rochelle, NY, that he met Norman Rockwell, who asked him if he’d pose for a series of illustrations of Tom Sawyer. He accepted the offer eagerly and was paid $3 an hour to pose for the famed illustrator. One of his depictions made it to a United States postage stamp in addition to Rockwell’s Saturday Evening Post series and museum in Stockbridge, Mass.
An alumnus of Iona Prep in New Rochelle, Gregory studied first at Manhattan College, studies interrupted by his service during World War II with the Army Corps of Engineers, then returning to finish his degree and go into the world of merchandising. But he quickly learned he was far more comfortable in the educational world and began his teaching career at Cheshire Academy in Connecticut. After that, it was a master’s degree from the University of Pittsburgh and eventual his long career at Shady Side.
The new Series was funded by an anonymous alumnus who wanted to pay homage to the educator who had been so important in his own life as a means of keeping the memory of the outspoken and distinctive teaching with the unique teaching style alive.
For more information on the Richard F. Gregory Visiting Writer Series or Shady Side Academy, visit shadysideacademy.org