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Oscar D’Angelo, ‘mayor of Little Italy’ caught in scandal, dies

Oscar D’Angelo in 1991.
Oscar D'Angelo once was considered the unofficial mayor of Chicago's Little Italy neighborhood. | File photo

Oscar D’Angelo, a charismatic, colorful confidant to every Chicago mayor since Richard J. Daley —and one whose deal-making courted controversy and scandal — died Sunday of prostate cancer.

Dubbed the “Mayor of Little Italy,” Mr. D’Angelo, 84, never left the old neighborhood, living across the street from the grocery store his Italian immigrant father owned at Laflin and Flournoy until the day he died. The D’Angelo family also owns a 15th-century Italian villa in the ‘Old Country.’

“His father was born in Italy, came to Chicago, worked odd jobs, saved his money and bought a building on South Laflin in 1939 when Oscar was eight years old. He was a grocer and a butcher who had a grocery store and meat market on the first floor of the building I’m living in,” said his wife of 31 years, Paula D’Angelo.

“This was his home. He loved this neighborhood. His brother moved to Highland Park and said, `Why don’t you come and live near me?’ And Oscar said, `Why would I want to leave when I have all my friends here. This is where my family found their fortune. This is where my Italian roots are.’ He became very involved in the urban-renewal process and wanted to make, as he said, `lemonade out of lemons.’ It was a blighted area at the time that he thought he could save and create a renaissance.”

He founded neighborhood organizations, railed against developments he deemed unsightly and patrolled the neighborhood in his Cadillac and on foot, often stopping to pick up litter or chastise residents for not keeping up their lawns. He slapped orange stickers on the windshields of illegally parked cars as if he were a parking enforcement aide.

Once, he was accused of muscling the second-generation owner of a neighborhood lemonade stand.

His City Hall influence dates back to the 1950s, when he cemented his relationship with Richard J. Daley by supporting the elder Daley’s most enduring legacy: the University of Illinois at Chicago. The UIC campus was built over the objections of Mr. D’Angelo’s Little Italy neighbors.

“They hung him in effigy. They protested him. They yelled and screamed at him. But, he had an enormous backbone. If he felt it was the right thing to do, he wouldn’t cower one bit,” said attorney Gery Chico, a longtime friend.

“Some thought I should be hung in reality,” Mr. D’Angelo once said of the opinion of his Little Italy neighbors on his support for the campus.

However, “Tens of thousands of students graduated from that institution, including me, because of Oscar’s efforts,” Chico said. “He was a fierce advocate for his community, getting the institutions and services he thought it deserved. But when he thought the greater good of the city would be served, he would even oppose those in his own community.”

That would not be Mr. D’Angelo’s only controversy.

In 1989, he was a private attorney disbarred for providing rental cars as gifts to judges, politicians and city officials in the wake of the federal investigation of judicial corruption known as Operation Greylord.

In 2000, he was back in the headlines, first for making $10,500 worth of interest-free loans to Mayor Richard M. Daley’s deputy chief of staff Terry Teele, then for his work as an unregistered lobbyist who raked in $480,000 while putting two friends of First Lady Maggie Daley — then-Economic Club President Grace Barry and public-relations maven Barbara Burrell — in business at O’Hare Airport.

The back-to-back scandals were so damaging, they prompted the younger Daley to publicly sever his 36-year friendship with Mr. D’Angelo.

But, Paula D’Angelo said the break with Richard M. Daley was more for “public consumption.”

“Oscar knew politics and the effect the media has on people in public office well enough that he understood the need to stay apart. Oscar and Rich would still have breakfast or lunch. But, it had to be away from the eye of the press,” she said.

Until his death, Oscar D’Angelo maintained what Paula D’Angelo called a “father-son” relationship with Daley’s son, Patrick. At one point after graduating from college, Oscar D’Angelo gave Patrick Daley the keys to an empty apartment in the building where Paula still lives.

“We saw [Patrick] growing up. Patrick just took a liking to him. Oscar has that charm. He loves young people. He likes to mentor them, in a sense. We don’t have our own children. He adopted young people along the way. Don’t all people sometimes find a friendship with an older person where they can reveal things they would be awkward to talk to their father about? That’s what happened between Oscar and Patrick,” Paula D’Angelo said.

Oscar D’Angelo was a man prone to excess. He didn’t just have dinner with Richard M. Daley. He bragged about co-hosting a 25th wedding anniversary party for the mayor in a letter to an O’Hare client.

Daley issued a statement Monday, saying “Oscar was as dedicated and hard-working as community leaders come.

“His neighborhood involvement was not just a pastime but his passion,” the former mayor said. “He loved Chicago generally and Little Italy specifically, and his unbridled enthusiasm and ideas, while not always popular, sometimes led to very positive change. Just as he gave his all as a neighborhood advocate, he was a devoted friend to many.”

When Randolph Street merchants dared to complain that Daley’s penchant for overgrown median planters was an accident waiting to happen, Mr. D’Angelo told them, “We spent $5 million to put those things in. I don’t care if three or four people have an accident.” When anyone dared to oppose him, he would bang his fist on tables and send them angry notes signed “O.”

“I never saw him threaten anybody … [but], what’s the line between bully and fierce advocate? I’ll take the fierce advocate,” said Chico, who moved to Little Italy and stayed there for a decade on Mr. D’Angelo’s recommendation.

Mr. D’Angelo went to the University of Chicago Laboratory Schools and earned a bachelor’s degree from the University of Chicago and a law degree from DePaul University.

His brother, Dino, was a clout-heavy real-estate investor and philanthropist who bought and restored the Civic Opera Building in the 1980s and was instrumental in revitalizing several downtown properties. Dino D’Angelo, who battled depression, died of a heart attack in September, 1991.

Like the mayors before and after her, former Mayor Jane M. Byrne told the Chicago Sun-Times in a 2004 interview that she relied on Mr. D’Angelo’s counsel and connections. Byrne recalled that he “had a lot of access in a lot of places, probably because of his brother,” that were put to use to help solve the busing and financial crises that plagued the Chicago Board of Education.

“I don’t think it ever made much difference to Oscar D’Angelo who sat in that chair. To him, to get in there, to be with the mayor, associated with the mayor and have his name mentioned with the mayor — and he wasn’t alone — is sometimes very helpful in business,” Byrne said then.

“He couldn’t do enough and he was great on ‘ruffles.’ He was like, ‘Protocol, I am it.’ He would say things like, ‘Good morning, Madame Mayor. What can I do for you, Madame Mayor.’ But you could cut through it all.”

Paula D’Angelo described her husband as a “consigliere to many” politicians. But it was even more important that he had “the biggest heart in the world.”

“It was not unusual for me to come home and find a stranger in my house who Oscar had picked up at a park he was cleaning. He’d say, ‘Give this fellow some work around the building and give him food.’ Then he’d pay him for his work,” his wife recalled.

“Once when he was down in Grant Park, a young man asked him for money. And he said, `If you work with me, I’ll buy you some food. Is that what you want?’ The man said he was trying to get to Denver to see his mother who was sick. So, Oscar brought him to the Greyhound station, bought him a ticket and waited with him until he got on the bus. He never saw that man again. Oscar was late for dinner that night. We had guests. I was very upset until I found out why.”

As for the influence-peddling allegations that dogged the mustachioed consultant/lobbyist who cozied up to Chicago mayors with Old-World charm, Paula D’Angelo portrayed it as a case of generosity misunderstood.

“Terry Teele was a dear friend. Oscar used to say, `What can Terry do for me? Get me a street lamp for Taylor Street?’ That was so out proportion. He needed money to pay a lawyer for his brother. We tried to help him out. Three months later, he repaid us. We didn’t know what the big deal was,” she said.

“The rental cars I want to say it’s something to laugh about. It was ridiculous. Friedman & Koven [the law firm where Mr. D’Angelo worked] represented Hilton and Hertz. It was not unusual for someone to call and say, `I can’t get a hotel room. Can you help me out? Or I’m trying to get a rental car. They’re all out. Can you make a phone call?’ Oscar would turn to his secretary and say, `Handle it.’ The secretary would get the invoice. Sometimes, it would get paid by the person requesting the rental car. Sometimes it wasn’t and it was no big deal. These were not humongous amounts. Oscar was singled out because of the fever of Greylord. They said it was rental cars for judges. But, Oscar was never a litigator and never appeared before a judge as a lawyer. I don’t know what the big deal was.”

Paula D’Angelo said she and her husband were “absolutely stunned” when Oscar was disbarred.

“Many people have said it was so unfair, Oscar should have gone back and tried to get his license back. We were told Oscar’s case was the only time someone was disbarred without ever being involved in criminal activity. It was a case of ethics,” she said.

Oscar D’Angelo. | Provided photo.
Oscar D’Angelo. | Provided photo.

Though he alienated some, “he was all about making that neighborhood as strong as it could be,” said Ald. Danny Solis (25th).

Solis recalled that when he first became 25th Ward alderman in 1996, Near West Side residents repeatedly asked him if he’d spoken with Mr. D’Angelo yet. Solis says he finally brought it up with Daley, telling him, “I keep hearing, ‘Oscar wants this’ and ‘Oscar wants that.’ ”

The mayor responded by reminding Solis, “You’re the alderman.”

Solis said Mr. D’Angelo laughed when he heard that — and confirmed that the mayor was right.

Mr. D’Angelo hosted Daley, Solis and other aldermen for dinner on occasion, Solis says. Then he’d let other people know about it. “He was a smart guy,” Solis says. “He’d use that to pick up his influence at City Hall.”

Ald. Edward M. Burke (14th), the dean of the City Council, recalled Oscar D’Angelo as “a man with a big heart whose mission in life was to protect the architecture, cultural integrity and very fabric of the Italian community that he treasured so much. He loved to walk down Taylor Street where he knew every person, shop, corner and stoop. When he looked into your eyes, he knew you generationally your mother, father, grandfather and cousins.”

And, Burke said, “he was a dear, charming, stubborn and engaging friend who will be impossible to forget and truly missed.”

In one of his last interviews, the always-outspoken Mr. D’Angelo talked to the Sun-Times about the marathon legal battle over Mayor Rahm Emanuel’s lakefront land giveaway to movie mogul George Lucas that ultimately cost Chicago the coveted $743 million private investment.

“I don’t think the Lucas Museum belongs in Chicago. It belongs in California. That’s where his work was done,” said Mr. D’Angelo, a board member of Friends of the Parks, the group that mounted the marathon legal challenge.

“I don’t think Chicago had anything to do with his success. I’m strained to find the rationale.”

A wake is planned from 3 to 11 p.m. Friday at Our Lady of Pompeii Shrine, 1224 W. Lexington. A funeral will be held at the shrine at 11 a.m. Saturday. Burial is to follow at Mount Carmel Cemetery in Hillside.

Contributing: Maureen O’Donnell