The 20th Ward of Chicago stands at a historic moment. It’s on the verge of tying with the 23rd and 31st wards, both of which have had three aldermen go to prison since 1972, for the unprestigious distinction of most aldermen convicted for corruption. Its current alderman, self-described “gangster” Willie Cochran, awaits a federal trial on bribery, extortion, and wire fraud charges. Over the last 30 years two of his three predecessors—Cliff Kelley and Arenda Troutman—have gone to prison for bribery and fraud.
Seasoned politicos—or those who have hired seasoned consultants—often devote significant resources to challenging their opponents’ paperwork and nominating petition signatures.
Accusations that Bailey was filing shotgun objections began flying from other candidates’ camps right away. Some hearing officers have so far agreed with the candidates he’s challenged.
“We’re not taking any evidence,” Shestokas said.
Dorf had no doubt that Shestokas would decide in Maddox’s favor. He handled the hearings on his own, leaving his client, the candidate, to campaign. After the hearing I asked Bailey why he wasn’t also working with a lawyer, preferring instead to waste his own campaign time hiking to the Board offices nearly every day and sitting through hearings that may last over an hour.
Bailey’s campaign signs are plastered on many vacant and boarded up buildings and his political organization, the Democratic committee, has grown in strength over the last two years to include the majority of election judges serving across the ward’s 39 precincts. This is due in part to the fact that his mother, Maria Bailey (who also serves as a notary and petition circulator for his campaign), was elected the Republican committee person back in the spring of 2016, at the same time Bailey became Democratic committeeman.
