Hall declared bankruptcy first at the age of 29, during his early career as a solicitor, having run up debts of more than £27,000. He was back in bankruptcy court six years later, in 1888. Even after his theatrical success and high salary from Edwardes, he was bankrupt again in 1898. His constant financial trouble stemmed from his gambling and extravagant entertaining of his friends. The pseudonym "Owen Hall" was an ironic nod ("owin' all") towards his extensive debts, as was another of his pseudonyms, "Payne Nunn" ("payin' none"). His sister Eliza recalled: "As a lawyer he gave advice freely to his friends; as a racehorse owner he indulged his prodigal proclivities in the world of hangers-on; during his editorial and play-writing epochs he was lavish in his hospitality ... and he voiced his belief that he 'had enjoyed every experience except death and solvency'." She wrote that, during his bankruptcy proceedings, Hall quipped irreverently: "Now I know that my Receiver liveth". His nephew Gilbert recalled that Hall said: "You can trust me with anything except a pretty girl or a sovereign."