On July 23, 1864, Menken sat down in her room at the Brunswick Hotel in London to write a cheerful letter to Ed James, who now worked for the New York Clipper:

“Theatre Royal Astley's” sounded grand, but by Menken's arrival Astley's had become a run-down amphitheater with a somewhat legendary past; only the grayest heads in London held memories of the theater's glory days as the site of magnificent equestrian drama. Nor was performing there Menken's first choice. She had originally planned to revise her stage image by working with playwright Dion Boucicault, of Octoroon fame. But by the time Menken arrived, financial difficulties had forced Boucicault to give up his dreams of revamping the ampitheater, and commercially savvy E. T. Smith had taken over management of Astley's. Menken then tried to reshape her image by pursuing a contract at the Drury, known for highbrow drama rather than circus acts. Failing that, she returned to Astley's to negotiate a generous contract to perform Mazeppa. Menken had clearly hoped to create a more respectable reputation as an actress, but circumstance forced her to swallow those hopes, and she instead embarked on an incredible journey toward fame, wealth, and celebrity.