Fortune building
Ryan opened a brokerage firm with two partners, Lee, Ryan & Warren, the following year.
In 1873 Ryan married his former boss's daughter, Ida Mary Barry, whose family were devout Roman Catholics. They had eight children. In 1874, his firm purchased Ryan a seat on the New York Stock Exchange. At the same time, Ryan became active in politics, especially with the Tammany Hall machine that controlled much of the city's operations, giving him political and industrial contacts across the city.
Ryan's fortune began in public transit. In 1883, he founded the New York Cable Railroad and bid on the proposed route from lower Manhattan to Midtown. After numerous legal and financial problems, in 1886 Ryan reorganized his cable railroad as the Metropolitan Traction Company. By 1893, construction of Ryan's rail system was underway on Broadway. Metropolitan continually acquired additional lines so that by 1900 it controlled 3,000 cars and 300 miles of track, the majority of New York's streetcar operations.
Ryan's most profitable investment was tobacco. Having invested in its stocks throughout the 1890s, Ryan joined tobacco assets in 1898, forming The Union Tobacco Company. Shortly thereafter, he merged Union Tobacco with his greatest competitor, James Duke of North Carolina, forming the American Tobacco Company. Together Ryan and Duke developed the British-American Tobacco Company to protect the American tobacco trade in Europe. Upon his death, Ryan also had major holdings in R. J. Reynolds and Liggett & Myers.
In 1905, amid public outcry, Ryan purchased the $400-million-strong Equitable Life Assurance Society, a major factor in the insurance industry. Although Ryan strove to make Equitable more responsive to its policy holders, public reaction to his purchase was overwhelmingly negative. His reputation for cutthroat business dealings in the streetcar and subway businesses made the public distrustful. In 1909, Ryan sold his Equitable stock. Also in 1905, Ryan's Metropolitan street car system was threatened by New York's increasingly popular subway system. He merged Metropolitan with August Belmont Jr.'s Interborough Rapid Transit Company. But the joint company's finances were shaky, and Ryan pulled out. Meanwhile, some $35 million that Ryan had raised in a bond issue were misappropriated. Ryan was investigated for corruption in 1908, but the grand jury brought no charges.
Ryan also invested in King Leopold II's Congo Free State. In 1906, he cofounded the American Congo Company with Daniel Guggenheim. He was also an investor in other Belgian colonial concession companies, including the diamond and lumber conglomerate Forminière.
Meanwhile, Ryan was making fortunes with coal mines, banks, public utilities and railroads. He owned Royal Typewriter and backed the maker of the Thompson submachine gun. At one time Ryan had controlling interest in 30 corporations.
