Early Life
Gregory was born in Southampton, where his father was a clergyman. He attended Banister Court school in Southampton. A classmate was Harold Davidson, the infamous Rector of Stiffkey. He attended Oxford University, but left before graduation. Gregory became a teacher, and later worked as an actor and theatre producer.
Much of the information about Gregory comes from his own papers and curriculum vitae, the truth of which is questionable. According to these sources, Vernon Kell, head of MI5, recruited Gregory in 1909, possibly because of Gregory's connections from London's nightlife. At MI5, Gregory mainly compiled dossiers on suspected foreign spies living in London. Later, Sidney Reilly allegedly recruited Gregory for the recently formed MI6. Gregory referred to his alleged time at MI5 and MI6 when he asserted that he had raised funds for the fight against Bolshevism. Official records verify that Gregory served as a private in the Irish Guards, but do not verify his time at MI5 or MI6. Gregory claimed that at about the same time he claimed he was working for MI5 and MI6, he became acquainted with Basil Thomson. Thomson was the Assistant Commissioner of Scotland Yard's CID. The relationship between Gregory and Thomson lasted for several years.
Read more about this topic: Maundy Gregory
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“... business training in early life should not be regarded solely as insurance against destitution in the case of an emergency. For from business experience women can gain, too, knowledge of the world and of human beings, which should be of immeasurable value to their marriage careers. Self-discipline, co-operation, adaptability, efficiency, economic management,—if she learns these in her business life she is liable for many less heartbreaks and disappointments in her married life.”
—Hortense Odlum (1892–?)