Crony of Duff Family Sentenced for Chicago HERE Contract Fraud

The final door in the eternal federal case against Chicago’s once-mighty Duff family has closed.  On January 27, Terrence Dolan, former operations manager for a Chicago-based company, Windy City Maintenance, was sentenced in federal court to 21 months of imprisonment followed by three years supervised release, ordered to pay $20,000 in restitution to the City of Chicago, and fined another $1,100 for his part in falsely indicating the firm as female-owned in winning a lucrative city contract back.  Dolan was the last of six defendants to be sentenced in a joint probe of a Chicago Hotel Employees and Restaurant Employees (HERE) local by the FBI, the IRS, the Department of Labor and the City of Chicago.  He had pleaded guilty in October to 11 counts of mail fraud.

James Duff, his brothers and their mother, Patricia Duff, ran Chicago’s Liquor & Wine Sales Representatives union.  James Duff also owned Windy City Maintenance.  In 1991 the company won certification as a woman-run firm, listing his mother as its head.  In so doing, Windy City obtained a contract to clean up after the Taste of Chicago food festival that year.  A rival bidder, questioning Mrs. Duff’s role in running company affairs, complained to city officials, triggering an investigation.  James Duff in turn taught Windy City Maintenance employees, among them Terrance Dolan, how to maintain the deception.  Eventually, in 1999, the firm was decertified as “woman-owned.”   A federal investigation ensued, with the Duffs being hit with a 30-count indictment in September 2003 on various charges, including racketeering and money-laundering.  The saga reveals much about corruption in Chicago, and perhaps more importantly, about the pitfalls of applying affirmative-action quotas to contracting.  (OLMS, 2/16/06).