Soards' New Orleans City Directories for 1890 and 1891 record Thomas C. Anderson as a clerk residing at 112 Prytania Street (old numbering), but by the next year Anderson had embarked on his first known business venture by opening a restaurant and bar at 12 North Rampart Street (112 under the new numbering system introduced in 1895). The restaurant was an immediate success, for Anderson provided a number of private booths where politicians, police and businessmen could hold private conferences, and arrange assignations in strict confidence. Tom was a good listener and knew the benefits that would accrue from keeping a closed mouth about his customers' affairs, both business and private.
At about this time, Anderson acquired a financial interest in a bordello at 172 Customhouse (Iberville) Street run by a young madam known as Josie Lobrano (1864-1914) who later went by the name of Arlington. It has often been said that he was Josie's lover, but the facts do not seem to bear out this assertion. Josie had been involved in a lengthy and violent relationship with Philip Lobrano (1847-1909), which ended late in 1890. Soon after she began to live in open concubinage with John T. Brady (1862-1930), and continued to do so until her death. However, there is no doubt that a strong friendship existed between Anderson and Josie Arlington.
In 1895, Anderson met a young police reporter on the New Orleans Daily Item by the name of Billy Struve, and the pair became lifetime associates. Their first venture was the successful Astoria Club in the Negro section of the city on South Rampart Street. By 1900, Struve was working full time for Anderson who had branched out into the oil business founding The Record Oil Company with a refinery in St. Bernard Parish and a depot in New Orleans. The 1900 U.S. Census recorded him living at 2131 Canal Street with his daughter, Irene, and listed his occupation as President, Record Oil Company. He later had major interest in the Protection Oil Company and Liberty Oil, which was subsequently acquired by Standard Oil.
He acquired the freehold of the Fair Play Saloon at the corner of Basin Street and Customhouse (Iberville) Street in 1897 and had rebuilt into one of the landmarks of the Storyville District when it opened for business in 1901. Renamed the Arlington Annex in 1905, it employed many jazz bands over the period of the next twenty years, and it has generally been referred to as Tom Anderson's. In all, Anderson ran three restaurant-saloon bars catering to the sporting trade in the early years of the twentieth century, The Stag at 712-714 Gravier Street, The Arlington at 110-114 North Rampart Street, and the famous Arlington Annex at Basin and Customhouse.
Anderson acquired the lavish bordello at 209 North Basin Street, next door to the Arlington Annex about 1904, and installed the young Hilma Burt as the resident proprietor. According to Jelly Roll Morton, Tom and Hilma were lovers and she continued to run the bordello until 1911 when she appears to have vacated the Storyville scene. 209 North Basin Street was taken over by an enterprising and cultured lady from Ohio by the name of Gertrude Dix who also stole Tom's heart.
In addition to all these activities, Tom Anderson represented the Fourth Ward in the State Legislature from 1904 to 1920. He served the legislature as a member of the Ways and Means Committee and also as a member of the Committee on Affairs on the City of New Orleans. In his electoral district, he dispensed favours, and was both lord and prophet.
With the passing of Storyville in 1917, Anderson's power in the Fourth Ward declined rapidly, and he was no longer able to help his constituents in the ways he formerly had. On 3rd February 1920 he was tried on a charge of knowingly conducting an immoral resort within ten miles of a military camp. The case ended in a mistrial, and it was Anderson's swan song in the sporting district.
Tom Anderson was a wealthy man, but he was also yesterday's man in New Orleans. He retired from business activity and acquired a home at 4630 St. Charles Avenue in the Thirteenth Ward where he lived quietly with Gertrude Dix. After a serious illness in 1928, he repented his former ways, as many sporting people did, and became a regular church-goer and benefactor to religious charities. Approaching seventy, he married Gertrude in September 1928, and lived with her and her niece in St. Charles Avenue until his death on 10th December 1931. (Orleans Parish Death Records, Volume 202, page 2962)
Tom Anderson left his wife, Gertrude, his entire estate, which was admitted to probate at approximately 120,000 dollars. It seems as though he had become estranged from his daughter, Irene, who had married one of his bar managers, George Delsa (1877-1924), on 21st April 1902. (Orleans Parish Marriage Records, Volume 23, page 936) George and Irene Delsa had 4 surviving children, Irene (born 1905), Marion (born 1908), Dorothie (born 1909), and Thomas (1915-2001). Twin sons, George Gottleeb [sic] and Thomas Cornelius, died a few hours after birth and a daughter died at three months of age. Irene Delsa contested the will on the grounds that Tom and Gertrude lived in open concubinage. Under the concubinage laws in Louisiana, a concubine could not inherit real property but could inherit up to one tenth of the movable property of the deceased. The court held that the concubinage laws were not applicable because the deceased had legally married Gertrude Dix. However, Gertrude Anderson generously settled a substantial portion of the estate on Irene as she felt she was entitled to an inheritance as Tom's legitimate daughter.