A part of 1st Ward politics for more than 60 years, Kenna possessed great influence on the municipal affairs of Chicago, being able to make or break the prospects of Democratic candidates for the mayoralty.

Possessing such influence despite his short stature and unassuming presence, he and Coughlin constructed a political machine that would last for the better part of the 20th century.

Kenna was notoriously corrupt; he, Coughlin, and several other aldermen led what was known as the "Gray Wolves", a group that attracted much scorn from reformers.

[2] He was born at the corner of Polk and Sholto (modern-day Carpenter) streets at the edge of "Connelly's Patch" on Chicago's Near West Side.

[8] According to legend, it was at this time that Kenna got the nickname "Hinky Dink" from Chicago Tribune publisher Joseph Medill due to his small stature;[5] as an adult he stood 5 feet 4 inches (163 cm) tall.

[21] When Carter Harrison III 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.

[26] 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.

"[32] 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,[32] formed his own Independent Democratic Party.

[33] Working with Sol van Praag, who had ambitions of his own to rule the 1st Ward,[32] he ran as a rival to Coughlin for the race and was endorsed by such publications as Mixed Drinks: The Saloon Keepers' Journal.

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

[35] Nevertheless, Kenna reassured Coughlin of victory[35] and used his organizational skills to bribe the homeless with fifty cents,[e] as much food as desired, and a place to stay for each voter.

[37] Kenna also recruited members of the Quincy Street gang to protect any voters of Coughlin, noting that the police would ignore any tactics used to that effect; in such efforts he preceded van Praag, who had had a similar idea, by a few hours.

[41] The resultant Ogden Gas Scandal sparked an outrage in Chicagoans and would prove a disaster to the local Democratic party[42] and especially Kenna's aldermanic aspirations.

[48] Kenna, recouping his forces in preparation for the 1897 race, saw that Coughlin could be of great use for Yerkes, and arranged for an alliance between him and rival 19th Ward alderman John Powers.

[49] 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.

That same year Carter Harrison IV would be elected mayor in large part due to Kenna's organizational skills in the 1st Ward.

[53] The Saturday before the election Harry G. Darrow, the proprietor of the new saloon The Bon Ton, issued an invitation for its grand opening, claiming that Kenna, Coughlin, and Harrison would be present.

[55] Nevertheless, Kenna openly displayed his gambling affiliation in response to a condemnation to that effect by the reform-minded Municipal Voters' League (MVL), stating "Sure, I associate with gamblers.

[65] Things would turn out differently in 1915 Scandal had befallen the duo with an exposé on the exploits of the Levee, leading to county judge John Owens's insisting that Kenna and Coughlin be ejected from the Democratic committee.

[66] Harrison acquiesced to these demands, declaring that Kenna's and Coughlin's careers were finished unless they towed the line and supported his entire slate of candidates, including Owens.

[68] Harrison was defeated in the 1915 mayoral primary by the Sullivan-backed candidate Robert M. Sweitzer,[69] who lost the general election to William Hale Thompson, an avowed enemy of Kenna and Coughlin.

[75] These parties were initially held in what would become Freiberg's Hall on east 22nd Street (modern-day Cermak Road),[75] and were marked by joy and peace with policemen being honored guests.

[78] Its reputation grew such that public pressure forced Mayor Fred Busse to withhold its liquor license in 1909; an event was still held at the Coliseum, but only 3,000 people attended.

[80] In particular, Big Jim Colosimo, who was a trusted precinct captain,[81] started to surpass Coughlin and Kenna and would soon take over representing the interests of vice.

[82] Within the ward the two were nevertheless safe as Thompson refused to challenge them directly, Colosimo remained on good enough terms with them, and the relief of vice obligations allowed them to concentrate on other matters.

[81] After alcoholic beverages were prohibited in the United States in 1920, The Workingman's Exchange had to close and Kenna ran a candy, sandwich, and cigar store in its place.

[8] Coughlin would find that the legislation increased his voting power in the council, while Kenna stated that he was content in his cigar store, where he hung up pictures of friends and prominent figures in the 1st Ward.

[94] For the last ten years of his tenure de facto power of the 1st Ward was held by a gang run by Jack Guzik, who used Coughlin as a figurehead prior to his death and Kenna thereafter.

[97] Budinger overwhelmingly won the election in the first round with what McVittie's supporters claimed were illegal and illegitimate tactics such as voter intimidation[99] and took office April 9.

[102] In 1943 historians Lloyd Wendt and Herman Kogan released the book Lords of the Levee, which concerns Coughlin and Kenna's activities.