Powerful Duff clan prospers from connections

January 23, 2005

BY ROBERT HERGUTH AND STEVE WARMBIR Staff Reporters

They've hobnobbed with famous politicians and infamous mobsters.

They've made millions off taxpayers and been hounded for unpaid bills.

They've fought for the working man as union leaders and engaged in quiet, lucrative deals with industry bosses.

They are the Duffs, a big, boisterous Irish clan with as many connections as contradictions. They are at the nexus of power in Chicago, where politics, big business, labor and organized crime converge.

The family likes to stay out of the limelight, but its workings come to light every so often in embarrassing locales.

Federal court, for instance.

There's James Duff, 46, the youngest of the Duff boys, who friends thought was destined for a life outside the rough-and-tumble world of the family.

He just pleaded guilty to defrauding the City of Chicago by setting up sham woman- and minority-owned firms to get a leg up on city contracts. Prosecutors say the scheme, which includes James Duff's mother, Patricia, swindled city taxpayers out of more than $100 million. James Duff's high-priced legal team disagrees, saying there was no loss to the city. The work, involving janitorial cleanup at public buildings and festivals, was done well, they say.

All in the family

James Duff is hardly alone among relatives in having public problems.

There is his 53-year-old brother, John "Jack" Duff III, who was thrown out of the Hotel Employees Restaurant Employees Union in 2000. An internal investigation found he essentially had a ghost job there. It also revealed that Jack Duff III once allegedly threatened to have a Florida police officer killed, along with his family, after the cop stopped Jack Duff III. A police report indicates he was picking up transvestite prostitutes.

And he has numerous organized crime ties, documents indicate. Just like his father.

John "Jack" Duff Jr., the 79-year-old patriarch of the family, rose from serving drinks at a bar to a union heavy who held huge sway over liquor deliveries throughout Chicago. He ran Local 3, which represents liquor warehouse workers and others, for years, followed by his sons.

His connections were vast, from hotel union chief Edward Hanley and late mob overlord Anthony Accardo to the two Mayor Daleys, sources said.

His clout, though, couldn't keep him out of federal prison in 1982, after he was convicted of union misdeeds both here in Chicago and in Detroit. Jack Duff Jr. got two years behind bars for some of those crimes.

In the Chicago case, Jack Duff Jr. was accused, but never convicted, of siphoning thousands of dollars out of a financially ailing Detroit local to give illegal bonuses to himself, his friends, and his son, Patrick Duff, back at the Chicago union.

One of those friends was William Stratton, who law enforcement sources say was affiliated with the El Rukn street gang and slain gang leader Mickey Cogwell. Stratton, who is black, also is accused of acting as James Duff's minority front in the current federal case targeting the family's businesses. Stratton's attorney, Michael Sher, said Friday that whatever Stratton may or may not have done in the past is irrelevant to the charges he faces at trial.

Given the Duffs' background, they aren't the type of people you would expect hosting fund-raisers for the current Mayor Daley. Or socializing with him at the old Como Inn, one of the Duffs' favorite hangouts. Or visiting the same health club.

In fact, a close friend of James Duff, former NFL player Guy Bingham, recalled meeting the mayor through one of the Duffs when Bingham visited town years ago.

Bingham was working out at a gym, hanging with one of the Duff brothers, when they ran into the mayor. Bingham was introduced.

Bingham played college football with James Duff at the University of Montana, and the two have stayed in touch, talking a little about the current federal case.

"What he said to me is, 'If they want to get ya, they're gonna get ya,' " Bingham said.

'Wife and girlfriend' take a trip

Booze is the wellspring of the family's empire.

Jack Duff Jr. was a child of Prohibition but as an adult he always had a hand in the spirits industry. He was a liquor store manager and bartender at "Duff's Tavern," when his first two boys, Jack Duff III and Patrick Duff, were born, records show.

By the time James Duff came along in 1958, the family had moved from the West Side to a quiet street with large frame homes in a historic part of Oak Park. While the dad kept his hand in the liquor business, he also rose in the labor movement. He would go on to control a distillery union along with his sons.

Back then, the West Side churned out mob bosses like an assembly line, and Jack Duff Jr. came to know some of them well.

Jack Duff Jr. explained it this way during the 1960 tax-fraud trial of the mob boss Accardo: Duff was in a tavern in the mid-1940s admiring a blue marlin mounted on the wall.

The bar owner, the late hoodlum Jackie Cerone, told him Accardo caught it.

"Congratulate him," Cerone told Jack Duff Jr., according to the testimony. "He is sitting next to you."

They shook hands and were pals ever since, Jack Duff Jr. told the court.

Accardo claimed he sold Fox Head beer for a living in the late 1950s, and the government believed it was a sham job to mask his racketeering income.

Jack Duff Jr. testified to buying beer from Accardo for Jack Duff Jr.'s liquor store, and for an American Legion Post that Jack Duff Jr. ran.

He also said Accardo and Cerone summoned him before his testimony to discuss what he would be saying.

Years later, it became clear they weren't the only gangsters Jack Duff Jr. was friendly with.

When his son, Jack Duff III, was in debt with a reputed mob bookie, rackets boss Rocco Ernest Infelise told Jack Duff III that he paid off that gambling debt as a favor to Duff's father, the son testified under immunity at Infelise's trial.

In another case, a conversation secretly recorded by the FBI revealed the elder Duff talking about mutual mob friends with a jeweler once convicted of receiving stolen gems.

Those friends included the mob's former man in Las Vegas, Anthony Spilotro, who was murdered in 1986, and Frank "Fifi" Buccieri, the late mob gambling boss, according to an affidavit.

The men chatted about Jack Duff Jr. buying jewelry, "and a trip which Duff had taken to Las Vegas, Nevada, with both his wife and girlfriend," the affidavit states.

An Irish ballad before jail

Through various court cases it became clear Jack Duff Jr. had plenty of connections, and a number of income streams.

After he testified in the Accardo trial, it came out that Jack Duff Jr. had a city job under the first Mayor Daley -- as a $4,380-a-year investigator in the law department.

A mayoral aide initially found "nothing wrong" with Jack Duff Jr. testifying for a notorious hoodlum, but later he was forced to resign. But Jack Duff Jr. had plenty to fall back on.

Aside from his other business interests, he was an officer with Retail Liquor Salesmen Union Local 162.

Jack Duff Jr. would come to control a related union, Distillery Workers Local 3 -- and run it with a crooked hand.

By the late 1970s, Jack Duff Jr. was secretary-treasurer there and vice president of the international union and had been sent to Detroit temporarily to help out a struggling local.

For his troubles, he thought he was entitled to the purse strings.

So he gave bonuses to himself, his son Patrick Duff, and their longtime union associate, Stratton, authorities alleged. Jack Duff Jr. was accused of diverting even more money from the struggling group to his union back home, Local 3, and the First Ward Democratic Organization, which for decades was controlled by the mob.

He was indicted by the feds, pleaded guilty in 1982 to two charges and was sentenced to six months work release and five years of probation.

His probation officer wrote about him then: "It can only be brought down to greed and disrespect for the lowly union man. Duff got greedy and used his position for his benefit and not to the benefit of the union members."

A second case also unfolded around this time involving union corruption, for which Jack Duff Jr. also pleaded guilty and was sentenced to two years in prison.

Before he left to do his time, a large going-away party was thrown at a restaurant.

One guest recalled him crooning "Danny Boy" to piano music.

Another person, a longtime family friend, attended a $200-a-head fund-raiser to help cover Jack Duff Jr.'s legal expenses.

"Here's a guy who stole from the liquor union, and they had a fund-raiser," the friend said. "And he pleaded guilty anyway."

Funny about money

If the fund-raising guest felt a little scammed by the Duffs, he's not alone.

Some family members were always working the angles, whether it was holding strange investment seminars or packing a union hall to ensure victory for their candidates or issues, numerous people said.

Even James Duff's high school friends were pressured to participate.

Some of them, along with Teamsters belonging to a unit run by the Hogan family, were recruited on occasion to pack the house when the Duffs faced a controversial vote at their union hall, sources said.

The friendly faces would show up early and pack the front rows. One of the Duffs or their allies would say, "I motion we raise the dues . . . because this union is doing a great job!" The house would cheer wildly.

The Duffs were no strangers to lawsuits claiming they weren't paying their bills, including a $14,000 bank loan.

But they could be ruthless in pursuit of a buck, a businessman said.

Jerry Weiland Jr.'s family for decades has run companies that move crates around McCormick Place for trade show exhibitors. Back in the 1980s, they needed extra help, so they hired the Duffs' temporary work-force company.

"I think they thought this is easy, so they tried to get our business," Weiland said, recalling that one of the Duffs approached convention contractors about hiring them for future events.

"I never used them again."

Daley connections abound

The main line of work for the Duffs' companies was providing janitorial and temp services, and they fared very well during the current Mayor Daley's tenure. Some attribute their success to their relationship with Daley.

He has acknowledged being friends with the family, but said he has nothing to do with their more than $100 million in municipal contracts, which have come since he was elected mayor in 1989.

Daley's brother, Cook County Commissioner John Daley, and Patrick Duff were named "Men of the Year" by a union council in 1999. Their fathers went way back, but John Daley said he didn't know how they met. He emphasized that the Duffs "are not from our community," meaning the South Side's Bridgeport enclave.

Sources suggest the late mayor and the elder Duff forged a bond through their mutual friend, Hanley, the late hotel workers union leader, who had a Land O'Lakes, Wis., vacation home.

The Duffs also had a rustic getaway nearby they recently sold for $1.5 million.

Hanley's son, Thomas, became tight with the Duff sons, drinking -- and roughhousing -- with the Duffs in the North Woods and in Chicago, sources said.

'Kill them one by one'

The Duff sons are described by people who know them as notorious tough guys.

No matter where they went, violence often followed, whether it was a brawl years back at a Cubs game, a knockdown fight at the Como Inn or another tussle at the old Lino's, sources said. One described the Como Inn as "a boxing ring" for some of the Duff sons.

The owners of the old Como Inn, however, describe the Duffs as customers so loyal they've followed the owners to a new restaurant.

One of the infamous stories concerning a Duff involves not violence, but just the threat of it.

In 1993, Jack Duff III threatened to kill a Miami Beach cop who was arresting him, according to a police report.

Jack Duff III had been in the back seat of a gold Cadillac Fleetwood that was blocking traffic in Florida. Around this time, union records indicate, he was helping run a mob-related bookmaking operation there.

The car was stopped, with "several well-known transvestite prostitutes at the right side of the vehicle, half in, thru the driver + passenger windows," the police report stated.

The car pulled away when police arrived, but soon was pulled over. As the driver was questioned, Jack Duff III became belligerent and was arrested. While being handcuffed he told the officer, Guillermo Berrier, "calmly" and "coolly" that if the cuffs weren't removed he would find the policeman and his family "and kill them one by one."

The cop was told that he "better listen" because Jack Duff III "has connections w/ organized crime in Chicago," the police report stated.

Jack Duff III was not prosecuted because he agreed to pay a fine and do community service.

Officer Berrier died in 2002 at age 39 -- but from diabetic shock, according to his parents.

'He knew better than this''

When he was arrested, Jack Duff III told the cops he was somebody else -- his brother, James Duff.

The younger Duff has ended up with the most notoriety of the clan, thanks to the current federal prosecution. But earlier in life, he was seen as the sibling least likely to follow in his father's footsteps.

Speaking about James Duff, a friend said, "He was a tough bastard, but he wasn't a mean kid. . . . That's what was so bad, he knew better than this. I remember him saying, 'I don't want to be like them.' . . . He didn't want to be what they were."