A part of 1st ward politics for about 50 years, he was a charismatic and eccentric figure who was well-known across the city and adored by his constituents; he and Kenna constructed a machine that would last the better part of the 20th century. He was the longest serving alderman in Chicago history until November 2014 when his record was surpassed by Edward M. Burke of the 14th ward. Notoriously corrupt, he and Kenna led the "Gray Wolves", a group that attracted much scorn from reformers; he and Kenna in particular were notorious across the nation and globe. He and Kenna were known as the "Lords of the Levee" after the Levee vice district that provided them with funds and support in exchange for protection from law enforcement.