Brown: Chicago loved Trump before it didn’t

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Donald Trump. | Getty Images

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It should not be forgotten how enthusiastically Chicago embraced Donald Trump 12 years ago this month when he blew into town and nodded to signal a backhoe operator to start tearing down the old Sun-Times building to make way for his shiny new skyscraper.

On that overcast day, Trump basked in the affection of an adoring crowd, people pressing him to autograph the dollar bills they waved aloft. Official Chicagodom put its arms around him, too, eager to feel the glow of the Trump brand — or maybe hoping to lift his wallet.

“Chicago is a truly great city, and we’re going to make it a little greater,” Trump promised his audience, before veering off topic to ask: “Is everyone going to watch ‘The Apprentice’ tonight?”

In her account of the event in “Donald Trump: Master Apprentice,” Trump biographer Gwenda Blair didn’t dwell on Chicago’s Second City bows to the New York businessman. But it’s part of what she finds striking in retrospect. Now that she’s a Chicagoan, too.

Blair, who moved here in 2011, says Chicagoans seemed to regard it practically as a “source of civic pride” that The Donald had chosen this city for his next big project, as if Trump’s recognition gave us new bragging rights.


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She found the celebratory mood a marked contrast to the “ruckus” of opposition Trump projects constantly stirred up in New York.

Gwenda Blair. | Matthew W. Stolper

Gwenda Blair. | Matthew W. Stolper

“Everybody was pleased as punch,” Blair recalls.

I met Blair by chance a couple of weeks back while interviewing people who had cast ballots in Chicago on the first day of early voting.

Now a Hyde Parker, she declines to say how she voted, explaining she doesn’t think it’s appropriate because she wrote a book about the Trump family.

That book — an exhaustively researched, 600-page tome originally published in 2000 as “The Trumps: Three Generations That Built An Empire” — places her among the nation’s handful of serious Trump biographers.


The book is currently being marketed under a new name: “The Trumps: Three Generations of Builders and a Presidential Candidate.” A spinoff, “Donald Trump: Master Apprentice,” has morphed into “Donald Trump: The Candidate.”

Blair moved here because of her husband, Matthew Stolper, who was then teaching at the University of Chicago and now serves as emeritus professor at the Oriental Institute. She continues to teach journalism at Columbia University in New York.

Blair’s particular niche is putting the Republican presidential nominee’s career in historical perspective with that of his father, Fred, and grandfather, Friedrich.

She describes all three as “extremely energetic, hardworking people” who each put his own wrinkle on a family culture of doing whatever it takes to come out on top.

Blair spent 12 years working on the first Trump book, even traveling to Kallstadt, Germany, the town from which the family hails, and to Whitehorse in the Yukon, to trace Friedrich’s steps during the Klondike Gold Rush.

I was surprised to learn it was there Friedrich made the family’s first fortune — not by prospecting for gold but by operating trailside saloons supplying miners with food, booze, gambling and access to women.

Blair’s observations about how Chicago embraced Trump seem particularly pertinent in light of the recent controversy over whether to remove the “Honorary Trump Plaza” street sign. As it happens, somebody has already done so without awaiting official City Council action.

My question was not so much whether we should take down the sign but why we ever put it up in the first place.

The building is its own monument to Trump — and it hasn’t been open even a decade. Why did someone think it necessary to further gratify his ego by naming the street after him? To flatter him, no doubt, but to what end?

Chicago is not expected to contribute many votes to Trump’s presidential bid. But make no mistake, this city did its part to make him who he is.

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