Hyde Park Media | Posted July 4, 2009

Full Disclosure: Former Chicago First Ward Alderman Don Parrillo and I met in late 2008. Someone I knew, knew someone he knew, and put us in touch. The former 1960's city politician was looking for a book editor. He did not want to talk to a reporter. He wanted to sell a book. "I've got gold," he said.

Something of a prospector myself, I took the alderman out for lunch.

But after reading his "manuscript" it was obvious to me at least he didn't have a finished book. At best, book notes - interesting anecdotes, unrefined nuggets - that would require considerable research and reasonable validation to be taken seriously as a book. At least a book I'd be willing to work on. That's what I told him.

"All I want you to do is clean it up a little," he barked.

"You can't say Bobby Kennedy had Marilyn Monroe wacked and just clean it up a little," I returned.

Over the course of the next four months, in between a handful of personal meetings, I spent hours on the phone listening to the alderman's intriguing mob tales, ultra-political rants, and ongoing adventures - from keeping his Viagra prescription filled to a recent DUI arrest in Indiana. All the while making it clear that I considered him - Ald. Don Parrillo - to be the real story and I wanted to tell it.

I also made clear, for the sake of credibility alone, he couldn't claim to be a mob insider without fully explaining how he got inside. And that meant talking at length about his father - a Prohibition-era district attorney and ward politician with alleged organized crime ties.

Again, Parrillo wasn't happy with my assessment. "I don't want to talk about that," he said.

Not long thereafter, the alderman and I stopped talking and eventually I started writing:

The Untold Stories of

Ald. Don Parrillo

By Anthony DeBartolo

CHICAGO - Former First Ward Alderman Don Parrillo, 78, is the most admittedly corrupt Chicago politician you probably never heard of. His relative obscurity, though, is not surprising.

who served from 1964 to 1968, has a lot of infamous First Ward aldermanic competition - from Michael "Hinky Dink" Kenna and “Bathhouse John” Coughlin to Fred (just Fred) Roti.

But even though they misspelled his name at times, he hasn't been ignored by the history books.

In former Chicago police reporter William Brasher's 1977 book, "The Don: The Life and Death of Sam Giancana," we're told the "First Ward aldermanic spot was finally bestowed on Donald Parillo, a young banker who was the son of William Parillo, a West Side politician with long-time allegiances to (Al) Capone and Jake Guzik...an alderman meeting (Sam) Giancana's requirements."

William "Billy" Parrillo
Mid-1930s newspaper clipping, city unknown

Alderman Parrillo intends to correct the spelling error and offer up a few Chicago Outfit stories of his own. "I started talking into my tape recorder," he says. "I've got 16 chapters."

"I name names unless the person is still alive or a member of their family is still alive," he says, adding with a laugh, "I want to stay that way."

"I've got a bunch of books," Parrillo says. "I'm going to end up with a TV show. What do you call it, a series. Every week me telling another story."

"We'll go to different locations and someone will say, 'Tell us what happened here, alderman.' And I'll tell 'em."

Right now, though, the alderman would be content with just one book.

About a year and a half ago, after having his tape recordings transcribed, Parrillo handed over a 173-page "manuscript" along with a $15,000 check to a Michigan Avenue vanity publisher he picked out of the Yellow Pages.

No book yet, but he does have a firm cover price, he says, "$24.95." There are also plans for a website, T-shirts, and coffee mugs.

"I want a picture of me sitting in a gold throne-like chair while I'm wearing two beautiful women on each arm," he suggests as possible book cover art.

As for a title, both "Capone May Go Free" and "A Society of Power" are under consideration, but the alderman prefers the former.

"Do you realize the name Al Capone is the most famous in the entire world?" he asked. "That's why Capone has to be in the title."

When it was pointed out Capone isn't given much space in his manuscript - save such tidbits as it was Jean Harlow who gave him the syphilis that killed him - Parrillo asked, "You don't know much about marketing, do you?"

Clearly, this former Chicago pol and Loyola University economics grad is a savvy businessman.

In the late 1950s, Parrillo founded what became the Westmont, Illinois-based Safeway Insurance Group, an auto insurance company now doing business in eight states.

When asked pointedly about the reputation Safeway seems to have for not paying auto claims, he seemed amused: "How do you think I'm a millionaire?"

According to the insurer's website, "Since its inception, Safeway Insurance has been under the leadership of Board Chairman and President William J. Parrillo."

"I started it," the alderman says, "then brought in my brothers," of which he has three.

While brother William runs Safeway, brother Robert is reportedly an attorney whose firm represents the insurer and routinely fights claims in court. The third brother, Richard, spun off his own insurance business in 1989 - the North Miami Beach-based United Auto Insurance Co. - which also seems to have a reputation for not paying claims.

As is not uncommon with family businesses, all is not well with the Parrillo brothers. The alderman says he's been feuding with Richard, William, and Robert in federal court over control of Safeway for years.

But only his apparently more personal feud with Richard, whom the alderman calls Dickie, has made its way into the papers.

The alderman once told the Chicago Tribune: "I've known a lot of gangsters who like to pretend they're legitimate businessmen. Dickie is the only legitimate businessman I know who likes to pretend he's a gangster."

"What I didn't tell them (the Tribune) was that they (real gangsters) were gonna kill the son of a bitch," Parrillo says.

"He was right out of college and was shooting off his mouth, saying things like, 'You know, this guy is a thief.' "

"He didn't grow up in the old neighborhood (Little Italy) like I did - he grew up in Oak Park. He didn't know real life wasn't like his fraternity."

"Twice I had to step in and tell him to keep his mouth shut," says Parrillo. "I told him there wasn't going to be a third time."

Alphonse Capone

By the early 1960s, Don Parrillo expanded his business interests by opening the Oak Park-based Parr Finance company. And unlike Brasher's history book, newspapers at the time spelled his name correctly after a 300-pound loan shark working out of Parrillo's office, William "Action" Jackson, was found dead in the trunk of his own Cadillac after having been tortured.

The mobsters known to hang around the loan office were "embarrassing to him," the Chicago Tribune reported Parrillo as saying in 1961, "but there was nothing he could do to stop them."

"I happen to be in the unfortunate position of knowing these guys," he said. "They were friends of my dad. I know them from the old neighborhood."

Apparently a tough place. "Three guys from my neighborhood died in the electric chair before they were 25," Parrillo says.

As for the alderman's dad, William "Billy" Parrillo, when he was only 24 years old, after graduating from the Chicago-Kent college of law, he joined the U.S. Attorney's Office of the Northern District of Illinois, Eastern Division, and was assigned to "handle liquor and libel matters," the Tribune noted in 1927.

(Fortuitous timing - 1927 was also the year bootlegging in general spiked after William “Big Bill” Thompson regained the mayor's office with the alleged help of Al Capone.)

Parrillo says after leaving government service, his father - who also served as 25th Ward Republican committeeman and was a member of the Illinois Commerce Commission - became a highly successful and wealthy criminal defense attorney, whose client roster included Al Capone, Frank Nitti, and Sam Giancana.

His dad clearly had clout. "He was widely credited with having made Dwight Green governor" in 1941, Parrillo says. What's not so clear is where the clout originated.

In "After Capone: The Life and World of Chicago Mob Boss Frank 'the Enforcer' Nitti," veteran organized-crime researcher Mars Eghigian, Jr. relays that the Feds became "suspicious" of the elder Parrillo while he was an assistant district attorney during their investigation of Capone.

According to Justice Dept. files, Parrillo's "office adjoined the grand jury room, and they suspected him of feeding inside information to the Capone interests. Though they could not prove perfidy without a shadow of doubt...authorities moved Parrillo's office to another part of the building, just in case," Eghigian wrote.

According to George Murray, a reporter for the Hearst Chicago newspapers in the 1930s, there was no doubt who Billy Parrillo worked for.

After he graduated from law school and "hung out his shingle, Al Capone became one of his clients," writes Murray in his 1975 book, "The Legacy of Al Capone." It was Capone, Murray contends, who "bought an appointment as assistant United States attorney" for Parrillo.

"In that period in Chicago the lawyer who had Capone for a client was in much the same position as the Renaissance painter in Florence having a Pope for a patron," Murray writes. "Parrillo's relationship to Capone was more than that of a lawyer to his client. Frank J. Loesch, president of the Chicago Crime Commission, on March 25, 1932, publicly identified Billy Parrillo as 'a known partisan of Capone.' "

"Yeah, I know," says the alderman. "My dad sued him."

One week after Billy Parrillo filed suit against Loesch for libel, he was publicly getting bad rapped again.

Nicholas Tesca, then a 42-year-old precinct captain for James J. Savage, a candidate for committeeman of the 25th Ward running against Parrillo, was shot and fatally wounded in front of his home. After being taken to the county hospital, the Chicago Tribune reported, but "before becoming unconscious, he blamed the attack on partisans of...Parrillo."

Regardless of exactly when the elder Parrillo switched teams - from prosecuting the likes of Al Capone to defending them - one of the first players the alderman got to know was Sam Giancana, who every now and then drove him and his brother to school as kids, he says. "I used to call him Mr. Sam."

"This was before Giancana was anybody. He'd come along with the boss to see my father at home very early in the morning before my dad went to his office. 'Take the kids to school and come right back,' the boss would tell him."

Asked who the boss was, Parrillo offered, "I never knew Al Capone because he went to jail when I was very young, but I knew Frank Nitti pretty well."

"You would never tell what the man did by just looking at him," the alderman says. "Quiet...mild-mannered...could have been a banker."

Parrillo got into banking himself in 1963 after selling off his loan company, and along with his brothers bought a 65-year-old west side bank, the Skala National, for $1,080,000. Later renamed the National Bank of Chicago, the vetting process the brothers successfully underwent by bank regulators led Giancana to ask "Donnie" Parrillo for a favor, he says. "That's what he called me, Donnie. Everyone knew me as Donnie back then."

"I was sitting in my office at the bank," says Parrillo, and another "old timer from the old neighborhood" - a politician and bookmaker from Chicago's Chinatown - dropped by with a message: "The Cigar wants to see you."

"The Cigar," Parrillo says, is what everyone called Giancana. "At least the people who knew him." No one ever called him "Mooney" or "Momo," the nicknames they gave him in the papers, he says.

"Tomorrow afternoon at 2:00 o'clock, go and visit your father's grave," Parrillo was told. Asking why never occurred to him. "Being from the old neighborhood, you learn not to ask," he says.

"So the next day I drove out to Mount Carmel Cemetery...It was late October I think."

"All the while there my mind was racing. I just could not understand what The Cigar could possibly want from me...I owed The Cigar nothing."

"My father was also his lawyer. He was always very pleasant to me and a fine guy in my opinion, so out of sheer respect, I went," he says.

As Parrillo drove through the cemetery, he saw "nobody was around, no other cars." There was, though, an old truck filled with gardening tools and a cemetery worker planting flowers not too far from the elder Parrillo's tomb stone.

Despite the fact he was planting flowers in late October, "I didn't pay much attention to him. So I got out of my car and went over to my father's grave."

"All of a sudden I hear, 'Donnie, Donnie, are you alone?' I look up, and there he is, dressed up like a farmer."

After asking about Parrillo's mother, who was quite ill at the time, and some friendly small talk about the old neighborhood, Giancana said, "Donnie, I want a favor."

"I'd be happy to do anything I can for you. You know that, just for old time's sake, if nothing else, and out of sheer respect. This is a second-generation friendship," Parrillo says he told Giancana.

But "The Cigar just repeated himself. 'I want you to do me a favor, a very important favor for me,' he said. This time he had a serious look on his face," says Parrillo. "I was more anxious than ever."

" 'I know since you bought the bank you've been cleared by the FBI, the National Bank Examiner and the National Controller of Currency,' he said. How he knew this, I didn't know, but I knew not to ask."

"Instead, I said, 'That's true, but what does that have to do with wanting to see me here today?' "

"He said, 'I need somebody clean that I can trust, somebody I've known all my life...I want you to become alderman of the First Ward of the City of Chicago.' "

" 'I don't want you to do anything illegal, and you'll never be asked to do anything illegal,' " Parrillo says he was assured.

" 'What about all the gambling that goes on in that ward?' I asked. 'Just ignore it,' he said. So, I asked him for a little time to think it over."

Two days later, Parrillo says he received a call from Benjamin "Buddy" Jacobson, as Giancana said he would.

"Have you ever heard of Buddy Jacobson?" Parrillo asked without pausing for an answer. "He was one of the four men shot in front of Holy Name Cathedral by the Dion O'Banion gang during the bootlegging wars. Two men died, two men lived, including Buddy. He said the first bullet hit him in the stomach and knocked him into the gutter, which saved his life because his body was shielded by the gutter. If you go by there today it's still a pretty high curb."

"So Buddy wanted to know what my answer was. The Cigar was waiting. I told him I would really enjoy doing him the favor, and I would enjoy being the First Ward Alderman - after all, I grew up in politics. But I couldn't, it would just interfere too much with my business," Parrillo said.

"But the main reason, I explained, was my new bride. She was totally against me getting into politics."

"Buddy said The Cigar was not going to like that answer - 'Nobody turns this guy down.' I said I'm really sorry, but there's nothing I could do. I thought that was the end of it."

The next day, Parrillo says he got another call from Buddy.
" 'Look at it this way,' he said. 'You'll make so much damn money by getting so many damn new bank accounts that you'll be more than happy you took the job. Now if your wife is your only problem, here's what The Cigar told me to tell you.' "

After confirming Parrillo wife's was indeed Irish, which to Buddy meant she liked to drink, he asked what her favorite restaurant was.

"The Whitehall, a private dining club on the near North Side," Parrillo explained.

"He said, 'Okay, here's what The Cigar said to do. Take her out to dinner tomorrow night at the Whitehall. There won't be any check for you, everything will be taken care of. Load her up with champagne, whatever she wants to drink. Get her good and juiced, then take her home, put her in bed and jump her. And while you're jumping her, say, 'Could I run for First Ward alderman?' "

"Well, the next night I took her to the Whitehall. When I pulled up in front of the door, there were two men there who took my car. We went in and ate and drank our fill. When I went to pay the check, they said it was taken care of. When I went to tip the waiter, they said that was taken care of. When I went to tip the Maitre D', that was taken care of. When I went to get my car, it was parked right at the door and had been washed. I was starting to get a little taste of how influential this guy really was," says Parrillo.

"So my wife and I went home, and we both had a little too much to drink...As I was making love to her, I said, 'Honey, is it alright with you if I run for First Ward alderman? And she said yes. "

"About 3:00 or 4:00 in the morning the phone rang and I knew before answering who it was. Without even saying hello, I said, 'Tell The Cigar he's got a candidate.' "

As welcome as that news might have been for Giancana, Parrillo wasn't exactly The Cigar's first choice for the job left open by John D'Arco Sr., longtime Democratic committeeman of the First Ward who was initially elected alderman 1951 and held the seat until 1963, when Giancana reportedly got angry with him.

State Senator Anthony De Tolve was slated to replace D'Arco on the ballot, but it's been said Giancana nixed that idea as well. Instead, Michael FioRito, a Wilmette attorney, was elected First Ward Alderman in February 1963 as a last minute write-in candidate. FioRito eventually resigned his city council seat when it became clear he wasn't even a resident of the First Ward.

Apparently not wanting to make the same mistake, two months prior to the January 1964 special aldermanic elections, Parrillo, along with wife Nancy, moved into the ward by taking up residence at the Executive House hotel on East Wacker Drive.

But after announcing his run as a "reform" candidate, Parrillo met some resistance. Both The Better Government Association and The Chicago Crime Commission publicly expressed disapproval of his candidacy - not that it mattered much. Parrillo already had the votes, he says.

"We had about 30,000 voters and at least 8,000 of those were on the payroll - either city, state, county or through the Municipal Employees Union, which the First Ward also controlled," says Parrillo. "Each job we put out was worth at least three votes, so we had about 24,000 votes to turn anyway we wanted...We could have elected Attila the Hun."

"The real power of the First Ward, and this is why I say in the book it was the First Ward that elected John F. Kennedy in 1960, was that the First Ward controlled 12 other wards."

The real difficulty Parrillo says he faced was making it look like a "real" election.

"For the first time in ward history" the election needed to be fought "on the square," says Parrillo, because the FBI was covering every precinct. "And this was the first time we had any real opposition" - Florence Scala, a much respected Italian community activist running as an independent, who said her election "would mark the beginning of the end for the hoodlums who have dominated the ward since the beginning of this century."

"As I said, we could have returned 24,000 votes but we didn't want it to be an overwhelming victory," Parrillo says, "so they decided I would get about 8,000 votes and she would get about 1,000."

According to press reports at the time, Parrillo received 8,685 votes; Scala, 3,622.

"The old timers were shocked" at Scala's high return Parrillo says. "Nobody ever did that against the First Ward Democratic Organization."

When Parrillo ran for reelection in 1967, he
went unopposed and there were no headlines. Indeed, despite his "reform" platform and pedigree, Parrillo didn't generate many headlines at all during his 5-year aldermanic tenure.

One exception, though, appeared immediately after the 1964 election - "I.V.I. Accuses Ald. Parrillo of 'Slander.' "

During a victory speech the alderman charged both the Independent Voters of Illinois and Roosevelt University with having "communist leanings." When asked why he made the charge, Parrillo bellowed, "Because they were communists!"

A second headline, "Nepotism Old Stuff on City Council Staff," included this item: "Mrs. Nancy Parrillo, a shapely blonde with a deep voice, started work yesterday as aldermanic secretary at $6,635 annually for her husband, Ald. Donald W. Parrillo [1st], a well-to-do banker."

"I've told you, you can't believe anything you read in the papers," Parrillo says. "Nancy never had a deep voice."

The alderman's last headline was apparently written in February 1968 when he abruptly resigned from the city council - "It Is Official: Parrillo Resigns; Denies Any Feud with D'Arco." When asked at the time why, Parrillo cited "business and family interests."

Paul "The Waiter" Ricca

Tony Accardo

The Chicago Outfit's business and family interests after Capone and Nitti were gone, veteran mob watchers will tell you, fell into the hands of either Paul "The Waiter" Ricca or Tony Accardo.

According to Parrillo, however, the two men ruled together. And it was with Ricca he had his closest relationship. When Parrillo's father passed away at age 48, while Parrillo was in his early 20s, "Ricca was like my surrogate father," he says.

"I'm going to tell you a story," declares Parrillo, "just to show you how powerful these guys were in the entertainment industry at the time."

"One Sunday afternoon (alleged events imply October 7, 1962) I was playing cards with friends, including Ricca's son, in Ricca's basement recreation room" at his three-story home in River Forest .

At a separate table "Ricca was playing poker with five other people. Periodically, we could hear music and applause coming from the third floor...Ricca's wife was entertaining some ladies' group."

"After a while, she came down to the recreation room with a very handsome young man from Italy who had a guitar strapped around his neck. 'Oh, Papa, I just love this young man,' she said. 'He's got such a beautiful voice. Can you help him?' "

" 'Well, what does he want?' Ricca asked his wife, who then turned to the young singer and asked, 'What do you want, young man?' "

" 'I'd like to be on the Ed Sullivan Show,' he said. So she said, 'When would you like to go on it?' and he replied, 'As soon as possible.' "

"Now, this is the hottest variety show in America and all the talent in America was trying to get on this show."

"So Ricca said to the guy seated next to him, 'Call the Jew in California and tell him to put this guy on the Ed Sullivan Show next Sunday.' "

"Well, the following Sunday I was glued to my TV set. And sure enough, about halfway through the show Ed Sullivan said, 'Now I'm going to introduce you to a handsome young Italian, the greatest voice from Italy.' And there he was [video]."

© 2009 Hyde Park Media