It’s tempting to make too much of Kevin Flynn’s role in snatching the Sun-Times from the jaws of death, the reason being that the bigger the role the richer the irony. Suffice it to say that Flynn belongs to the investment group assembled by James Tyree that on Monday took control of the Sun-Times and the other 58 titles that compose the Sun-Times Media Group.

Ten years ago Flynn and his father, Donald, were heading up their own investment group, which expected to profit handsomely from opening a casino in Rosemont. But the Flynns ran into opposition. In 2001 the Illinois Gaming Board stripped the Flynns’ Emerald Casino Inc. of its gaming license, punishing the Flynns for “a continuous pattern . . . of providing false and misleading information to the Board” and citing, among other things, a lack of due diligence regarding prospective shareholders “who are associated with persons who have been identified as members and associates of organized crime.” On March 29, 2002, the Sun-Times editorial page denounced the Flynns as the fiasco’s “marquee villains.”

So what we have today is an awkward situation.

The Flynns fought back against the gaming board, and in 2005 former federal judge Abner Mikva conducted a hearing into the matter. He concluded that the board had done the right thing. As Chris Fusco reported in the Sun-Times on November 16, 2005, Mikva wrote that Emerald played “fast and loose with the law and with the rules and regulations” of the gaming board and that its “modus operandi seemed to be ‘catch me if you can.'” Various parties “dissembled” when Emerald was first trying to move into Rosemont, Mikva found, while Kevin Flynn “flat-out lied.”

Another Sun-Times editorial on the Emerald project appeared on November 16, 2003. Earlier the paper had merely railed against the Flynns. This time it lectured them.

“The big losers in all this, of course, are Donald and Kevin Flynn,” spoke the Sun-Times. “They invested $20.6 million they will not get back, but they have no one to blame but themselves. . . . You pay your money, you take your chances.”

Kevin Flynn understands how the game is played, and he’s anted up again. He wouldn’t tell me how much of the $26.5 million that bought the bankrupt media group was his, but he knows it’s at risk. “It’s speculative,” he allows, putting it mildly. “It’s obviously an interesting time to be getting involved in media.” But like Tyree, he asserts this is about more than money. “It’s an important investment in Chicago, an important investment in jobs. It’s important to keep a world-class city like Chicago having two major papers.”

Since the Emerald deal collapsed, Flynn has moved on in life—yesterday’s casino magnate is today’s repo man. He has various irons in the fire, but the business taking up most of his time is Renovo, which bills itself as the “premier provider of vehicle transition services” and claims to be “changing the face of repossession.” He’s not one to look back. “I was involved in a project that didn’t work out the way I wanted it to,” says Flynn. “And I certainly would have wished that it had been covered a little differently. But that’s kind of the way it goes sometimes. I unequivocally do dispute several of the assertions that were made by the gaming board. [But] at this point in time I would rather like to put that chapter of my life behind me.”

That might be easier for him to say than it is for the Sun-Times to do. “I am choosing to be positive under the circumstances, given the alternative is no Sun-Times and no job,” says Fusco, who over the years has covered Flynn more than anybody else at the paper. “When you consider the people who have run the paper in the past, how they ran it into the ground and some of them went to prison, the Sun-Times doesn’t exactly have a track record of squeaky-clean ownership.

“One of the things I’m hoping is that the new owners understand they’ll have to end the Conrad Black-David Radler era if the newspaper is to survive. Some of these people who own us [now] have been in the news in the past and presented in lights that we know they couldn’t have found favorable to them. But I’m hoping these new owners understand they’re inheriting a newspaper that has been plagued by questions of integrity. They’ll need to end that era if the paper is to survive. Everything needs to be kept at arm’s length—not only for the sake of the reporters but for the sake of their protecting their own investment.”

Observe Fusco speaking in the plural. Tyree assembled a colorful bunch. Among the other new owners of the Sun-Times is Wirtz Corporation president “Rocky” Wirtz, liquor distributor and chairman of the Chicago Blackhawks, a major Sun-Times sports beat. Also the brothers William and Robert Parrillo, identified by Tyree as “private investors.”

The Parrillos’ dad, the Tribune reminded us on October 17, did legal work for Al Capone. Their brother Donald is a former alderman of the First Ward, a post he says he was recruited for by late mob boss Sam Giancana. Brother Richard has been a crony of and big-time fund-raiser for George Ryan and Ed Vrdolyak. But if there’s a family business, it’s auto insurance. William founded Safeway Insurance, whose interests Robert, an attorney, then looked after in court by litigating claims. Richard heads up the United Automobile Insurance Group.

A long 1993 article in Chicago Lawyer reported that, according to a former partner, the informal motto of Robert’s law firm was “Negare, Tardare, Non-Solitio”—deny, delay, don’t pay. The article questioned whether Robert, whom it identified as at one time the company’s biggest single shareholder, holding 39.8 percent of its stock, could serve both the interests of policyholders seeking prompt, generous settlements and Safeway, which would benefit from slow, grudging payouts.

In 2005 an article in New Times of Broward/Palm Beach, “The Bad-Hands People,” described Safeway as a firm that “routinely fought claims in court” and said that “Richard Parrillo brought the same philosophy to Florida when United Auto was founded 16 years ago.”

I faxed Robert Parrillo with questions about his past experiences with the press and how they might bear on his new adventure. The reply was from his administrative assistant. “The purchase of the Sun-Times is viewed as an opportunity sustain an important part of Chicago’s tradition and have Chicago to remain a two-paper town,” she wrote me. “Other than that as an occasional contributor to the Chipmunk Chatter (the camp Shewamegon newsletter) Mr. Parrillo has no particular relationship or experience with the press. Mr. Parrillo currently has no expectation of influencing the coverage of the STMG papers.”

My “other questions and observations” (about family matters), were, she told me, “not relevant to the purchase of the Sun-Times.”

Though the Chicago Lawyer piece had Robert saying, “The best story about me is a blank page,” it did not describe him as unobtrusive, as someone who would never dream of calling a city desk. “In the last six years,” it read, “he’s filed seven suits involving such things as his office’s air conditioning, a TV remote control, and bathrooms. He sued over bathrooms twice.”

“Anybody in the business that does investigative reporting has had calls placed to their publisher by people they were writing about,” Fusco says. “Despite it all, I’ve never had a story that hasn’t gotten in the paper. Tyree insists he’s going to be the public face of the operation, and he insists he’s not going to get involved [in the paper]. Right now we have no choice but to take him at his word.”   

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