In February 1902, Graydon gained publicity for his participation in a charity performance with the Barnum & Bailey Circus.

Their "Romeo and Juliet" romance, in which Graydon helped his bride escape from a New York boarding school, garnered national media attention.

The groom was a roommate of the bride's brother at Harvard; and the blonde fullback whose plays on the gridirons at Cambridge and New Haven were acclaimed by thousands of admirers, has long been known to the Whitneys as 'Tommy' ... She was about the age of 15 when she met and fell in love with 'Tommy' Graydon ...

According to contemporaneous press accounts, Graydon trained as a cobbler in Cincinnati after graduating from Harvard—hoping to learn the shoe business.

[1] In 1909, the couple garnered national press attention again when Mrs. Gradyon sued for divorce, alleging that her husband failed to support her.

[10][11][12][13][14][15][16] One press account of the trial reported on the testimony of Graydon's wife and father-in-law: Idleness, dissipation and neglect on the part of Graydon entered into her disillusionment, she explained, and he had allowed his business in Cincinnati to dwindle away until it did not bring enough revenue to provide for her support, she said.

According to Mrs. Graydon, selling shoes proved less attractive to her husband than bucking the line of Yale in football scrimmages, and his experience as a business man was marked by none of the eclat that distinguished his career on the gridiron.

[18] When the United States entered World War I, Graydon enlisted and was sent to the Plattsburg training camp.

Graydon and his third wife died when their automobile was involved in a collision with a passenger bus near Westfield, Indiana in October 1949 while the two were returning from Santa Monica, California to their home in New York.