Upon his return to Chicago Kenna opened a saloon on Clark Street known as the Workingman's Exchange where he doled out meals to the indigent in exchange for votes.
Above the Workingman's Exchange was the Alaska Hotel, which could provide space for 300 men, and up to 600 during elections.
By 1882 his saloon was a success and he was a fixture in the 1st Ward Democratic organization under Chesterfield Joe Mackin; his work in securing Grover Cleveland's victory in the 1884 election led Mackin to make him captain of his precinct immediately prior to being imprisoned for fraud related to that election.
It was at this time that Kenna first encountered John Coughlin, although the two would not become close friends for a while.
Coughlin, who had in his early life served as a bathhouse masseur, was popularly known as "Bathhouse John" or "The Bath".
When Coughlin was first elected as alderman in 1892, Kenna helped the campaign as he normally would but did not make any extra effort.
When Carter Harrison ran for mayor in 1893 Kenna was to quick to support him while Coughlin was one of the last holdouts, straining relations between the two.
However, Harrison's betrayal of Kenna by prosecuting him for gambling just like others in the 1st Ward, as well as the rise of the detested rival Billy Skakel, led Kenna to reconsider an alliance with Coughlin as McDonald's influence started to wane.
In 1893, Kenna proposed an alliance which Coughlin readily accepted.
Coughlin was the public face of the machine while Kenna would work in the background.

Kenna started the new organization by proposing that a defense fund be organized from protection money from brothel keepers and gamblers to legally defend members of the organization who got into trouble.
From such fund two lawyers would be retained at $10,000 a year to represent organization members; Kenna and Coughlin themselves paid the initial $10,000.
The future judge John R. Caverly, who would later preside over the trial of Leopold and Loeb, received his first fees from this fund.

For the special mayoral election triggered by Harrison's assassination, Kenna and Coughlin broke with traditional Harrison supporters by supporting John Patrick Hopkins.
Kenna is noted as a member of the Cook County Democratic Party Central Committee for the 1st Ward as of December 21, 1893, serving alongside John P. Leindecker.
He succeeded James Walsh, who had been alderman of the 10th Ward from 1883 to 1885.

An early example of Kenna's organizational skills was the 1894 aldermanic election.
Coughlin was unanimously nominated as the Democratic nominee in what Lloyd Wendt and Herman Kogan would later call "the briefest political convention in Chicago's history" and was reported  by the Chicago Herald as lasting "only a few minutes as the delegates were in a hurry to get away to attend a prize fight."
However, rival Billy Skakel, who specialized in offering and soliciting gambling on fraudulent stock quotations and hated Coughlin for allowing local Prince Hal Varnell to cut into his turf, formed his own Independent Democratic Party.
Working with Sol van Praag, who had ambitions of his own to rule the 1st Ward, he ran as a rival to Coughlin for the race and was endorsed by such publications as Mixed Drinks: The Saloon Keepers' Journal.
Fearing for his career despite Kenna's insistence that he would win, Coughlin visited Hopkins, who unsuccessfully asked Skakel to withdraw from the race.
Coughlin then presented a petition to get Skakel's name removed from the ballot, which was initially accepted by the election board but would later be overturned by a local judge and backfire on Coughlin.
 Nevertheless, Kenna reassured Coughlin of victory  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.
Kenna also suggested that Coughlin visit Hopkins once again and remind him of how the duo had helped him avoid scandal in a gas-boodling concern.
After Hopkins once again pled with Skakel to withdraw to no avail, he ordered the police department in t
Upon his return to Chicago Kenna opened a saloon on Clark Street known as the Workingman's Exchange where he doled out meals to the indigent in exchange for votes. Above the Workingman's Exchange was the Alaska Hotel, which could provide space for 300 men, and up to 600 during elections. By 1882 his saloon was a success and he was a fixture in the 1st Ward Democratic organization under Chesterfield Joe Mackin; his work in securing Grover Cleveland's victory in the 1884 election led Mackin to make him captain of his precinct immediately prior to being imprisoned for fraud related to that election. It was at this time that Kenna first encountered John Coughlin, although the two would not become close friends for a while. Coughlin, who had in his early life served as a bathhouse masseur, was popularly known as "Bathhouse John" or "The Bath". When Coughlin was first elected as alderman in 1892, Kenna helped the campaign as he normally would but did not make any extra effort. When Carter Harrison ran for mayor in 1893 Kenna was to quick to support him while Coughlin was one of the last holdouts, straining relations between the two. However, Harrison's betrayal of Kenna by prosecuting him for gambling just like others in the 1st Ward, as well as the rise of the detested rival Billy Skakel, led Kenna to reconsider an alliance with Coughlin as McDonald's influence started to wane. In 1893, Kenna proposed an alliance which Coughlin readily accepted. Coughlin was the public face of the machine while Kenna would work in the background.
Kenna started the new organization by proposing that a defense fund be organized from protection money from brothel keepers and gamblers to legally defend members of the organization who got into trouble. From such fund two lawyers would be retained at $10,000 a year to represent organization members; Kenna and Coughlin themselves paid the initial $10,000. The future judge John R. Caverly, who would later preside over the trial of Leopold and Loeb, received his first fees from this fund.
For the special mayoral election triggered by Harrison's assassination, Kenna and Coughlin broke with traditional Harrison supporters by supporting John Patrick Hopkins. Kenna is noted as a member of the Cook County Democratic Party Central Committee for the 1st Ward as of December 21, 1893, serving alongside John P. Leindecker. He succeeded James Walsh, who had been alderman of the 10th Ward from 1883 to 1885.
An early example of Kenna's organizational skills was the 1894 aldermanic election. Coughlin was unanimously nominated as the Democratic nominee in what Lloyd Wendt and Herman Kogan would later call "the briefest political convention in Chicago's history" and was reported  by the Chicago Herald as lasting "only a few minutes as the delegates were in a hurry to get away to attend a prize fight." However, rival Billy Skakel, who specialized in offering and soliciting gambling on fraudulent stock quotations and hated Coughlin for allowing local Prince Hal Varnell to cut into his turf, formed his own Independent Democratic Party. Working with Sol van Praag, who had ambitions of his own to rule the 1st Ward, he ran as a rival to Coughlin for the race and was endorsed by such publications as Mixed Drinks: The Saloon Keepers' Journal. Fearing for his career despite Kenna's insistence that he would win, Coughlin visited Hopkins, who unsuccessfully asked Skakel to withdraw from the race. Coughlin then presented a petition to get Skakel's name removed from the ballot, which was initially accepted by the election board but would later be overturned by a local judge and backfire on Coughlin.  Nevertheless, Kenna reassured Coughlin of victory  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. Kenna also suggested that Coughlin visit Hopkins once again and remind him of how the duo had helped him avoid scandal in a gas-boodling concern. After Hopkins once again pled with Skakel to withdraw to no avail, he ordered the police department in t
Michael Kenna