David Radler remembers the phone call from Donald Trump sometime around the year 2000. Trump said he was out on the street sizing up the old Sun-Times building, which stood on the north bank of the river on the east side of Wabash. Not that Trump had any interest in the Sun-Times building itself, but as he told Radler, it occupied the best site in the city. “I want to do a deal,” said Trump.
Radler was publisher of the Sun-Times and COO of Hollinger International, which owned the paper. Radler also wanted to do a deal. He and Trump soon met. “There weren’t a lot of preliminaries,” says Radler. “I told him the price. He paid the price. There was no crapping around—no gamesmanship.” The price was about $75 million. “He got what he wanted. We got what we wanted,” says Radler. “He was a perfect partner. He did everything he said he would do.”
I had several phone conversations with Radler when he ran the Sun-Times from 1994 to 2003. He felt underappreciated then and still does. The dim public view of Radler is not likely to do a 180: Chicago will long remember him for the broad strokes of his tenure. Radler and his business partner Conrad Black, Hollinger’s CEO, were bounced out of office in a shareholders’ rebellion in 2003 and indicted on fraud charges in 2005. Radler pleaded guilty to one count, testified against Black at the 2007 trial, and spent ten months in prison. He now owns a string of small papers in western Canada.
On the other hand, it was Radler who assembled Hollinger’s “Chicago Group,” the Sun-Times plus the string of suburban daily and weekly papers that their owners post-Hollinger never exactly knew what to do with and recently sold to Tribune Publishing. And Radler wants me to know that when he was shown the door in 2003 the Chicago operation was making more money than ever before—or, it goes without saying, ever since. And Radler did the deal with Trump, giving Chicago a building universally acclaimed until Trump slapped his name on it in letters the size of a football field.
Back then, says Radler, there were two Donald Trumps. “There was ‘the Donald,’ who was what you’re probably seeing a lot now, and there was the Donald Trump who was a serious businessman. I saw the other one—’the Donald’ would sign autographs on dollar bills when we were walking in the streets of Chicago. But the real Donald Trump was a really formidable businessman.”
The reason for my call was to find out if Radler thinks Trump is presidential material. I confess to prejudices in this area, and Radler’s views would tell me something about Radler as well as Trump.
“Yeah, I would vote for him,” Radler says. I ask why. “Because I think he’s perhaps one of the most qualified people to be president. Was Mitt Romney qualified to president?” I suppose he was. “Is this guy not as qualified as Mitt Romney?” Romney had been a governor, I say, but Radler waves that credential away. “The big difference is Trump stood up and admitted, ‘Yes, I have money! I’m wealthy! I make money!’ Mitt Romney was hiding it all the time. So who had the better temperament?”
Mitt Romney, in my view, which is colored by Trump’s attitude toward women and flogging of poppycock ideas such as building a fence to keep out Mexico. “Without getting into that stuff, which obviously isn’t tasteful,” says Radler, “the basic difference between him and Mitt Romney was that Mitt Romney was afraid to admit he was wealthy. Trump is being brutally honest. I don’t want to get into mudslinging, but the man [Trump] is so much more qualified to be president than your current president, by whatever standard you use. He was totally unqualified. He never ran a peanut stand. He never met a payroll.”
If you still ran the Sun-Times in 2008, I wonder, would your papers have endorsed Obama?
“Probably, sure,” says Radler. “But he was the local candidate.”