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. In the late 19th century Chicago would award franchises to private companies for construction of such utilities as gas and public transit, the latter of which would prove contentious in Chicago. Businesses seeking such lucrative contracts would bribe and otherwise work with the aldermen in a practice known as "boodling". 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. Despite being almost invariably excoriated by the Municipal Voters' League Coughlin himself was re-elected 19 times and never defeated, running unopposed in his last four elections. Indifferent if not enthused about his reputation for corruption, upon being accused of corruption he demanded a retraction not for the charge of graft but for the claim he was born in Waukegan.
