There is no evidence that Sullivan in any way originated the idea for two companies, and he probably became first involved by convincing his political partner, Mayor John P. Hopkins not to veto the ordinances.
[1] His main political opponent within the local Democratic Party, five-time mayor Carter Harrison IV suggested in his autobiography that each of the original shareholders made about six hundred thousand dollars.
Before this point, contrary to expectation, both companies began a profitable operation (quashing the belief that they were created to force the local gas monopoly to buy them out).
The historian Forrest McDonald in his work on Samuel Insull has conceded that Sullivan introduced a new approach to municipal politics by forgoing raids on the public till, and confining himself and his associates profits from city contracts and jobs, all within the boundaries of the law.
The feud stemmed supposedly from Bryan's alleged belief that Sullivan's election to the national committee had been engineered through fraudulent means (which was not true), but in reality it was based in Bryan's long-term antipathy to Sullivan that originated in the Chicago Democratic being a leader of the Gold Democrats, who opposed the Great Commoner in 1896 with their own candidate, Illinois' John M. Palmer.
It was said (though much that is "said" about the convention is questionable) that Sullivan and Indiana boss Thomas Taggart forged a deal with one of Wilson's aides in a Baltimore hotel room while all three men were clad in their pajamas; the deal allegedly involved putting Thomas Marshall on the ticket as vice president in exchange for the Indiana and Illinois delegations throwing their support to Wilson.
[3] Sullivan did not get as much for his trouble-as he hoped-he was denied complete control of federal patronage by the administration (until 1916) and it did little (thanks to Bryan, who was secretary of state) to help him when he ran for the U.S. Senate in Illinois in 1914.
Sullivan lost despite having the opposition split between Progressives and Republicans, largely as a function of the G.O.P reuniting and claiming its place as the state's majority party.
When he died, his passing was greeted with expressions of grief from Woodrow Wilson, Republican Governor Frank Orren Lowden, and virtually the entire Illinois political establishment, reformist or not.