Charles Myron Clegg, Jr., was born in Youngstown, Ohio. His father owned a wholesale produce business. When still a boy, the family moved to Providence, RI, to Pidge House located on North Main Street.

At about the age of 12, Chuck developed an interest in (and a talent for) electronics; specifically radio. At that age, he became the youngest licensed radio operator in the country and built and operated his own station, W8DTE.

Upon his 21st birthday, Chuck was given an envelope (by his father) that he had hoped would contain some sort of monetary gift in acknowledgment of the occasion. Instead, he was presented with an 'eviction notice' from the house effective that very same day! After all, this was a common tradition in eastern families of comparable social status, and was normally reserved for the oldest male child.

Upon arriving in Washington in the mid-1930's, Chuck took employment at a 'specialty house' as a junior executive. At the eve of WWII that Charles Clegg and Lucius Morris Beebe were, by simple chance, invited to a party given by Evalyn Walsh-McClean, in Washington, DC.

From there, Chuck and Lucius developed a love relationship based also on a common bond: railroading. Chuck and Lucius moved to a New York City where Chuck was to become a departmental executive at yet another specialty shop on Fifth Avenue. However, Pearl Harbor intervened, and Chuck enlisted into the Naval Reserve instead.

In the Navy, Chuck was given the commission of radio technician (something at which he was well suited for). Chuck' friends noticed that his uniforms were tailor-made and non-regulation, and often included a gold watch chain identical to the one Beebe wore.

Cleggs and Beebe, together, wrote several books about railroads. After Beebe's death, his lover Charles Clegg inherited the bulk of Beebe's estate. He died 13 years later.