Kenna was corrupt, but he had his limits. When transit magnate Charles Yerkes offered him a bribe to vote for Yerkes's interests, Coughlin reported the incident to Mayor Carter Harrison, Jr, explaining that Yerkes had offered too much. Coughlin's attitude was you could get just as rich in the long run accepting small bribes, and take less of a chance of getting caught.
Coughlin and Kenna's best-known activity was the first ward ball, an annual fundraiser which brought together safecrackers, prostitutes, politicians, businessmen, gamblers, and others. 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 ended, the ball had moved into the Chicago Coliseum and ended in annual riots.
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 for the first ward to his partner. He remained a ward committeeman until his death.