[2] The son of a Greek shipping magnate,[3] Theodoracopulos was privately educated in the United States at Lawrenceville School and Blair Academy[4] before attending the University of Virginia.

[8][9] He has also written for other US and UK publications, including Esquire, Hamptons Magazine, Newsweek, the New York Press, The Sunday Times, and Vanity Fair.

[10] In 1984, Theodoracopulos was arrested for the possession of cocaine, after attempting to board a plane at Heathrow Airport, and served three months in HMP Pentonville.

"[17][18] In a 2021 interview, months after many Golden Dawn leaders were convicted by Greek courts for heading a criminal organisation, the chairman of The Spectator, Andrew Neil, who does not have influence over the magazine editorially, condemned the column, stating it was "beyond the pale".

[25] He has used the racial epithets "nigger" and "Sambo" to describe black people[26] and he referred to Saudi royal family members as "ruling towelheads".