The play was first produced by Liebler & Company, staged by Eugene W. Presbrey, with settings by Gates and Morange, and starred Kyrle Bellew.

[3] Presbrey revised it considerably; among other changes, he added a character called Captain Redwood from an 1886 play, Jim the Penman, to provide Raffles with a significant opponent.

[5] Presbrey used plot elements of two short stories in The Amateur Cracksman, "Gentlemen and Players" and "The Return Match", which are connected by the affair of Lady Melrose's diamonds.

[6] George C. Tyler says in his 1934 memoir that he tried to interest E. W. Hornung and Arthur Conan Doyle in pitting their creations, Raffles and Sherlock Holmes, against each other in a stage play.

[12][13] The local critic found interesting the dramatists explanation of Raffles condition as a disease of the mind, and credited him with a play that keeps the audience's attention throughout.

[18] The Washington reviewer noted that "Mr. Presbrey, who made the dramatization, has been a little too fatherly" with Raffles, "with Ibsenish hints at heredity" and efforts to build sympathy for a character always on top of every event who doesn't need it.

The critic for The Baltimore Sun found no fault with the play; they said Kyrle Bellew's Raffles was believable and the audience heartily approved the performance.

[21] The New-York Tribune reviewer was dismissive of suave, elegant thieves as a stage novelty, and even more so of crime as a mental disease or aberration.

They did recommend seeing the play for E. M. Holland, "who repeats in it, under new circumstances, his old achievement of seeming languid indifference veiling vigilent attention and splendid executive force, in Jim the Penman.

[26] Leander Richardson in The Buffalo News said Kyrle Bellew was popular with the "matinee girls" who hung around the stage door to see him after daytime performances, something that didn't happen when he played "virtuous" roles.

[28] The story is set in Brittany during 1793, and deals with a defrocked priest (Bellew), a fugitive count (Connor), a tenant farmer (Roberts) and his granddaughter (Blandick), and a brutal agent of the revolutionary government (McCormack).

It was originally planned for a two-week run as a holiday supplement,[29] but proved popular and was continued as long as Raffles remained at the Princess.

[30] On February 4, 1904, the Princess Theatre and five other venues were shut down by order of Mayor McClellan for failure to comply with directives issued by the Building and Health departments of New York City.

[32] Producer George C. Tyler sent the Raffles company to play one-night stands in smaller New England cities,[33][34][35] until performances on Broadway could be resumed on February 15, 1904, at the Savoy Theatre.

[37] It was still profitable after 168 performances, but Kyrle Bellew and several others of the cast were booked for a revival of The Two Orphans,[38] and the theater was to be closed for alterations to bring it in compliance with a new fire code.