At age 10, Kenna left school and began selling newspapers. By age 12, he had borrowed $50 from a barkeeper and purchased a newsstand at the corner of Monroe Street and Dearborn Street. He was so successful that he was able to pay back the loan within a month. According to legend, it was at this time that Kenna got his nickname from Chicago Tribune publisher Joseph Medill, because of his small stature. Even as an adult, Kenna stood just 5 foot 1 inch (156 cm) tall.
Kenna and his partner, fellow First Ward alderman "Bathhouse" John Coughlin, were known as the "Lords of the Levee", a district included in their ward which provided them with the support of prostitutes, pimps, tavern-owners and gamblers.
Coughlin and Kenna were also known for hosting the First Ward Ball, an annual fundraiser which brought together gangsters, safecrackers, prostitutes, politicians, businessmen, gamblers, and other types as well. The event raised more than $50,000 a year for the two men until it was closed down in 1909 by Mayor Fred Busse. By the time it was banned, the ball was so large that it had to be held in the Chicago Coliseum, the city's major convention center. Besides its notoriety in attracting many unsavory characters it often ended with the police having to curb disorderly conduct bordering on rioting.
In 1923, the number of aldermen per ward was lowered from two to one, and Kenna stepped aside to become a Ward Committeeman, leaving the alderman's position of the First Ward to his partner. Aldermen were elected by their constituents and were paid a salary while Committeeman were elected by precinct captains and were paid from the coffers of their political party. Hinky Dink remained First Ward Committeeman until his death from myocarditis and diabetes at age 89 on October 9, 1946.
Although he left his heirs an estate worth over one million dollars, and an additional thirty-three thousand dollars to be used to erect a mausoleum for his remains to repose in, his heirs took all of the money and bought him an eighty-five dollar tombstone instead. 
- "Rites Saturday for Hinky Dink, An Era's Symbol". Chicago Tribune. Chicago, IL: Tribune Co. 1946-10-10. p. 4.
- Wendt, Lloyd; Herman Kogan (1974). Bosses in Lusty Chicago (a.k.a. Lords of the Levee). Indiana University Press. p. 73. ISBN 0-253-20109-8.
- Abbott, Karen (2007). Sin in the Second City: Madams, Ministers, Playboys, and the Battle for America's Soul. New York, NY: Random House. p. 58. ISBN 978-1-4000-6530-1.