Daley Duff
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

Over the years, Mayor Daley has tried to downplay his relationship with the controversial Duff family, who he’s taken campaign money from and socialized with, even though some members of the clan have reputed mob ties.

But FBI documents obtained by the BGA raise fresh questions about just how close the Duffs were to Daley—and what sort of City Hall access they enjoyed during the mayor’s soon-to-end tenure.

This past July, the BGA requested the FBI file on patriarch John F. “Jack” Duff Jr. Duff—ex-con, disgraced union boss, and self-described pal of late mob chieftain Anthony Accardo and other hoodlums—died in 2008 at age 82, permitting the release of certain law enforcement files available to the public under the Freedom of Information Act.

The FBI recently released more than 600 pages that include intelligence from informants and witnesses, newspaper clips, subpoenas, notes from agents and other material, most if not all relating to Duff.

Although numerous names and other details were redacted, Daley is referenced directly or indirectly more than 20 times. While there’s nothing in the documents to suggest the mayor did anything illegal, he’s not always mentioned in the most flattering light.

In one document that summarizes a FBI interview with an unidentified individual, the person recalled seeing Duff “sitting at a table together” with Daley and “several” unnamed aldermen at the Como Inn during a Christmas party held by the Duffs.

Later in the same document, from 2000, the Duffs are described as “assisting Mayor Daley with promoting certain individuals for election.”

And there’s this line: “[Blanked out] said it was common knowledge that Jack Duff, Jr. and Mayor Daley were close friends and that Jack Duff, Jr. had direct access to the mayor.”


In the decade or so after Daley was first elected in 1989, companies affiliated with the Duffs reaped more than $100 million in local government contracts, generally for janitorial work, cleaning up everything from the Taste of Chicago to McCormick Place and the Harold Washington Library.

At the same time, the Duffs donated more than $30,000 to mayoral campaigns, and organized fundraisers for Daley, according to published reports.

In the late 1990s, the media began raising questions about whether companies with ties to the Duff men were fraudulently getting government business by posing as woman- and black-owned enterprises. (A portion of local government contracts is “set aside” for companies run by minorities. The Duffs are white.)

The FBI investigated, and ultimately Duff’s wife, Patricia, and one of their sons, James, were charged with participating in what was found to be a massive minority-contracting scheme. James Duff was convicted in 2005 and still is serving time in a federal prison in Duluth, Minn., records show. Charges were dropped against Patricia Duff because she was facing serious health problems.

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Another Duff son, John F. Duff III, was not charged in the case but has been investigated by federal agents for organized crime activities—including allegedly running an illegal gambling ring in Florida with reputed mobsters, records show. In another instance, during a traffic arrest in Miami Beach, he threatened to kill an officer if handcuffs weren’t removed, and told the policeman that he “better listen” because John F. Duff III “has connections [with] organized crime in Chicago,” according to the police report.

The elder Duff had deep connections to the Chicago mob, testifying on behalf of Accardo at the mobster’s 1960 tax-fraud trial that they did business together and were friends. Duff was working for the first Mayor Daley at the time, but later lost his job.

Duff ended up in charge of a labor union representing workers in the liquor industry, but served prison time in the 1980s after being convicted of embezzling union funds.

One of the FBI documents obtained by the BGA described Duff as having “strong ties to Organized Crime in Chicago and…close personal friendships with Outfit [member] Anthony Spilotro,” among others.

Over the years, the current Mayor Daley has acknowledged knowing the Duffs and accepting campaign help from them—and he’s faced criticism for this—but he has tried to portray the relationship as nothing special, saying at one point, “I know a lot of people.”

A spokeswoman for Daley echoed that thought, telling the BGA: “It’s difficult to respond to statements made by anonymous people, but suffice it to say that after 22 years at the helm of a city as mayor, you know a lot of people.”

Members of the Duff family, and their lawyer, did not return phone calls.

Meanwhile, Daley isn’t the only interesting mention in the FBI records.

One unnamed person relayed to the FBI that he “got the impression that the Duffs had contacts in the Cook County Sheriff’s Office,” according to an FBI document that appears to be from 2000.

And a “cooperating witness” relayed to an FBI agent in 1994 that Duff had an insider’s perspective on then-U.S. Rep. Dan Rostenkowski—the powerful Chicago Democrat who would go to prison in a corruption scandal.

According to FBI paperwork, Duff told the cooperating witness “that Rostenkowski was going to be indicted and charged with stolen stamps, and gifts which were given to employees by Rostenkowski.”

Duff added that “Rostenkowski felt as though he (Rostenkowski) would have no problem confronting these charges in court, if that is all they (the Government) had against him,” according to the document. Rostenkowski ultimately pleaded guilty to two counts of mail fraud, and spent more than a year in prison. He died last summer.

Beyond Daley

The reputed mob ties of John F. Duff III, the secretary-treasurer of a Chicago union long controlled by his family, have been well publicized in recent years.

But Illinois political figures—including Gov. Pat Quinn, Cook County Treasurer Maria Pappas and state Rep. Jim Durkin—still accept campaign donations from the group.

Quinn, a Chicago Democrat friendly with organized labor, accepted $1,000 from the political action committee of the Duffs’ Liquor & Wine Sales Representatives Local 3 early last year, just days before a fierce February primary that he ended up winning, according to the Illinois State Board of Elections.

Quinn has taken a total of $2,600 from Local 3 since 2002, records indicate.

Pappas, also a Chicago Democrat, accepted $1,500 in September from the same PAC, according to the elections board. It appears to be her first Local 3 contribution.

Neither Pappas nor Quinn returned phone calls from the Better Government Association on the topic.

Durkin, a Western Springs Republican, accepted a $500 donation from Local 3 in 2010 and a $500 donation this year, records show. He’s taken a total of $3,750 since 2005, state records show. (Durkin told the BGA their families are both West Side Irish and “go back years,” but that he doesn’t know anything about the mob allegations.)

Duff once was investigated by the FBI for alleged involvement in a mobbed-up gambling ring in Florida. He is paid $183,733 a year by Local 3, and holds the No. 2 position there, after his brother Patrick, according to documents filed by the union with the U.S. Department of Labor.

Neither the Duffs nor their attorney returned calls seeking comment.

DOCUMENTS — John F. “Jack” Duff Jr. FBI File

John F. “Jack” Duff Jr.—ex-con, mob associate and supporter of Mayor Daley—died in 2008, making part of his FBI file accessible to the public under the Freedom of Information Act.

The Better Government Association obtained more than 600 pages of documents under FOIA from the FBI, and is making them available for public review.

Although many of the names are redacted in the documents, there are more than 20 references to Daley. To find them, scroll through the pages or search for keywords such as “Daley” or “mayor.”