[1] Michael, a native of County Roscommon, had come to the 1st ward in 1857,[1] and owned a moderately-successful grocery at Polk and Wells before it burned down in the Great Chicago Fire.

Coughlin's tenure was marked by a large amount of corruption, in which he, Kenna, and 19th ward alderman Johnny Powers led the Gray Wolves, a group of notorious aldermen.

Such antics ultimately led to the creation of the reform organization Municipal Voters' League to run and endorse candidates in opposition to the Gray Wolves.

[5] Despite being almost invariably excoriated by the Municipal Voters' League Coughlin himself was re-elected 19 times and never defeated,[6] running unopposed in his last four elections.

"[11] However, rival Billy Skakel, who specialized in offering and soliciting gambling on fraudulent stock quotations[11] and hated Coughlin for allowing local Prince Hal Varnell to cut into his turf,[11] formed his own Independent Democratic Party.

[12] Working with Sol van Praag, who had ambitions of his own to rule the 1st ward,[11] he ran as a rival to Coughlin for the race[12] and was endorsed by such publications as Mixed Drinks: The Saloon Keepers' Journal.

[12] Fearing for his career despite Kenna's insistence that he would win,[13] Coughlin visited Mayor John Patrick Hopkins, who unsuccessfully asked Skakel to withdraw from the race.

[14] Nevertheless, Kenna reassured Coughlin of victory[14] and used his organizational skills to bribe the homeless with fifty cents, as much food as desired, and a place to stay for each voter.

[16] Kenna also recruited members of the notorious Quincy Street gang to protect any voters of Coughlin, noting that the police would ignore any tactics used to that effect,[17] preceding von Praag, who had had a similar idea, by a few hours.

[19] Kenna ran for alderman in 1895, but van Praag and Skakel took vengeance for the events of 1894 and with the help of a controversial franchise to the Ogden Gas Company aided Republican candidate Francis P. Gleason to defeat him.

[24] Coughlin and Kenna took their revenge on Powers by defeating his bid for the chair of the Cook County Democratic Party Central Committee in favor of free silverite Tommy Gahan.

[28] This united the reformers, who felt that the City was being deprived of tax dollars, and the corrupt aldermen, who saw their sources of profit vanish, to oppose Yerkes's efforts.

[29] He decided to make Coughlin the leader of opposition of a bill in the General Assembly to allow the seven gas companies of Chicago to merge into one and form a monopoly.

[30] Coughlin and Kenna were also the hosts of the First Ward Ball, an annual political fundraiser which brought together safecrackers, sex workers, gangsters, politicians, businessmen, gamblers, and a variety of other types.

By 1933 a report on Coughlin's unopposed run in that year's aldermanic election by the Associated Press described him as a "Vestige of a past era" and "the epitome of a vanishing [type of] American".

[36] Coughlin set the poem to music[37] and had the daughter of a friend sing it after Emma Calvé refused,[38] performing it at the Chicago Opera House on October 8.

[40] A 2012 retrospective by NBC News Chicago ranked Coughlin and Kenna as the 3rd and 4th most corrupt public officials in Illinois history, behind William Hale Thompson and Paul Powell.