In 1888, Barrington left the D'Oyly Carte organisation and the Savoy Theatre, missing the chance to create the role of Wilfred in "Yeomen", to try his hand at theatrical management, leasing the St. James's Theatre. The "Illustrated Sporting and Dramatic News" lamented Barrington's departure, suggesting that he was irreplaceable in the Savoy Operas: "He is the typical embodiment... of that British Philistinism, the pachydermatous hide of which Mr. Gilbert has so long striven to penetrate by the process of holding up its own image before it." In March 1888, Barrington played Chrysos in a benefit performance of Gilbert's "Pygmalion and Galatea", a role that he would reprise at a number of "benefit" performances over the years. Later in the year, at the St. James's, Barrington produced "The Dean's Daughter" by Grundy and F. C. Phillips, also playing the Very Reverend Augustus St. Aubyn, Dean of Southwark. Though the piece was unsuccessful, Barrington's performance was praised, and it launched several theatrical careers, including Olga Nethersole's. Gilbert's "Brantinghame Hall" (an abject failure), starred Barrington as Mr. Thursby, as well as his younger brother, Duncan Fleet, Julia Neilson and Lewis Waller (the latter two in their professional stage debuts). Its companion piece was "A Patron Saint". This experiment in management proved to be a financial disaster for Barrington, and he was bankrupt after only five months.