Shady Associations: Mayor Daley Held to Lower Standard

To read the main story, and to see the 600-page FBI file, click here.

John F. "Jack" Duff Jr. (shown at left in a 1960 photo) headed a politically connected family that won $100 million in city business. Mayor Daley acknowledges he knows the Duffs but also says, "I know a lot of people." | Sun-Times Library photos

Under a long-standing consent decree between the federal government and the International Brotherhood of Teamsters, union members are barred from “knowingly associating with any member or associate” of organized crime.

So if, say, a Teamster truck driver for the City of Chicago has drinks with a Paulie Walnuts type of guy, and investigators for the union find out, bada bing! That truck driver can hit the road—meaning he or she will likely be kicked out of the union.

But there’s no such restriction placed by the city on the ultimate boss of those municipal truck drivers: the mayor of Chicago.

Which is interesting, because it just so happens that the outgoing Chicago mayor, Richard M. Daley, has over the years “knowingly” associated with at least one reputed organized crime figure: John F. “Jack” Duff Jr., a convicted union embezzler and an admitted mob associate who died in 2008.

The Better Government Association recently obtained the FBI files on Duff, and Daley is mentioned more than 20 times. The mayor is not accused of doing anything illegal—but the indication is that he and Duff were quite friendly.

Daley’s press secretary excused the FBI report away by saying the mayor knows a lot of people.

Indeed. Among his other long-time pals: Fred Barbara, a trucking magnate who once was arrested in an organized crime extortion case, but later was acquitted. More recently, Barbara was accused by a witness at the Family Secrets trial of participating in the mob bombing of a suburban restaurant in the 1980s. Barbara wasn’t charged in that case, and in a past interview has denied involvement in organized crime.

Either way, we’d like somebody to clear this up for us: Why is it alright for an elected leader to associate with allegedly shady folks, but it’s not alright for worker bees to do so?

Yes, we understand we’re mixing apples and oranges here a little. After all, unions are private entities, and city government is public. And elected folks ultimately answer to voters, unlike rank-and-file workers.

But when talking principle, should those distinctions matter?

Or should we just fuggedaboudit?

This story was reported and written by Robert Herguth, the BGA’s editor of investigations. Contact us with tips, suggestions and complaints at (312) 821-9030, or at


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