You may recall an entertaining Twitter spat that broke out between reality-TV turned reality-politics star Donald Trump and Pulitzer-winning Tribune architecture critic Blair Kamin. A few years ago Trump built a generally well-received addition to the skyline, and in the manner of someone labeling his stapler at work, decided to come back around and stick his last name on it. Kamin, in his role as person who evaluates architecture, wrote that it was a garish "wart" on a "handsome skyscraper" that is otherwise a "plus for the skyline."

Trump, in his role as person who yells at people on Twitter, went ballistic on Kamin, calling him a "third rate architecture critic" for the "failing @chicagotribune."

Kamin got off easy compared to his predecessor, the late Paul Gapp, who was also a Pulitzer-winning architecture critic for the Chicago Tribune. Gapp was a prolific writer of considerable depth and intellectual breadth—finding time not just to cover the city's skyscrapers but the architecture of gentrification and criminal-justice facilities—and recognized by his peers for it. But his achievements were overshadowed by his run-in with The Donald: a $500 million lawsuit over one column, about Trump's plan to build the tallest building in America in Manhattan.

Gapp was not afraid of ambitious architecture. He found much to praise in Helmut Jahn's outlandish and largely infamous Thompson Center, frequently lamented then as now. In a lengthy review informed by his considerable learning, Gapp wrote that "the center succeeds brilliantly in its interior in most respects, but fails as an object on the cityscape. Guy de Maupassant used to enjoy lunching at the restaurant inside the Eiffel Tower because that was the only place in Paris where he could not see the iron giant. Many will no doubt come to feel the same way about Jahn's center."

It was Trump's economic ambitions that made Gapp skeptical. In 1984, Trump proposed a 150-story, 1,940-foot tower on the East River at the southern tip of Manhattan. Gapp trained his practiced eye on the idea, concluding that "the world's tallest tower would be one of the silliest things anyone could inflict on New York or any other city." But Gapp's argument was not aesthetic; there was, at the time, no rendering to make an aesthetic judgment on. (Though he did call Trump's claim that it would "balance" the World Trade Center "eyewash"). It was merely practical.

Statistics provided by Trump indicate that he plans on a slender building. Such structures are economically inefficient at extreme heights because so much space in their interior cores must be devoted to elevator shafts, fire stairs, and a myriad of mechanical entrails.

Partially as a result, Gapp wrote, "the availability of $1 billion for such an unprecedented and ego-propelled real estate gamble is not at all certain."

One thing worth noting: Since there was no official rendering, the Tribune ran an artist's conception of the skyscraper with the article.

At a certain point, the economics of supertall skyscrapers hit economic limits before they hit physical ones. As Paul Goldberger—another architectural writer to draw Trump's wrath—writes in Up From Zero about the challenge of replacing the World Trade Center:

Indeed, in the months following September 11, despite the proclivity of architects to conceive of new forms that skyscrapers might take, it was common to hear that very tall buildings were dinosaurs, not just at Ground Zero but everywhere. They had come to symbolize fear as much as romance… and in any event who could afford them? The antiskyscraper crusaders forgot that the very tallest buildings had rarely made economic sense, that they were generally exercises in vanity as much as profitability, and that there hadn't been a single supertall office building put up in the United States since the Sears Tower, in Chicago, was finished in 1974…. Long before September 11, it had become clear that the future of skyscrapers in the United States, such as it was, was going to be in new designs for buildings of forty, fifty, or perhaps seventy-some stories…. American developers had been quite happy to concede to Asians the mega-skyscraper category, realizing there was far more money to be made in building lots of medium-size towers than a handful of supertall ones.

Gapp concluded his piece on Trump's proposal: "[F]our years ago, this critic predicted that nobody will ever build a skyscraper taller than Sears Tower. That prediction still stands."

He was prescient. In the United States only One World Trade Center has exceeded the Willis Tower, a decision made in large part for aesthetic and cultural reasons, and achieved only with a very tall mast. [Clarification: The Willis Tower has been exceeded by nine other buildings in the Middle East and Asia.] But there's only one person in the world who's going to decide what Donald Trump is going to do, and that's Donald Trump. He filed a lawsuit in federal court in the Southern District of New York, and the district judge, like many people who cross paths with the developer's Quixotic wrath, seemed to enjoy it very much, rubbing Trump's nose in Gapp's evaluation:

After a careful review of the record, this court has no doubt that the statements contained in the Tribune article are expressions of opinion. The very presentation of the article in the Sunday Tribune Magazine section, under the heading of the "Design" column, with a byline identifying the author as the Tribune's "Architecture Critic," informs the reader that the article embodies commentary by a Tribune columnist, and is not a news story reporting factual material. From the first sentence, which describes the "only remotely appealing aspect" of the Trump project, the prose is cast in subjective terms; the very words Trump objects to, which refer to the proposal as "one of the silliest things anyone could inflict on New York" and describe the asserted aesthetic balance between the proposed tower and the World Trade Center as "eyewash," convey to the reader the highly personal and subjective nature of the judgments expressed.

The judge, Edward Weinfeld, concluded by giving Trump the business.

Plaintiff, having sought publicity for his proposal, finds that defendants do not like his proposed structure. He, on the other hand, does not like their conception any better. The words of the Latin proverb are particularly appropriate here: De gustibus non est disputandum, there is no disputing about tastes.

Trump kept pushing, drafting Thompson Center architect Helmut Jahn for Television City, a 1,670-foot tower for NBC. ("New York has always had the world's tallest building until very recently, when Sears Roebuck built a somewhat taller building than we have, and, I would also say, a much less attractive building than we have," Trump told the Tribune.) Gapp would have the last laugh; economics and community opposition killed the idea.

Trump tried one more time, two decades later. Chicago's Trump Tower was originally intended to be a 2,000-foot building, and he'd actually gotten to the planning stage with the go-to architect for supertalls, SOM's Adrian Smith. This time a more grave reality derailed Trump's ambition—Smith was about to present his plans to Trump when the events of 9/11 began. In response, Trump scaled the building back to skyline size, where it found favor until he slapped his name on the side.

But his relationship to Smith gave him one last shot at a deal, as Kevin Nance reported in the Sun-Times:

Still later, however, Trump toyed with the idea of further heightening the tower by adding an elongated spire that would make it the tallest building in the world. He approached Smith, who put a damper on the concept, in part because he was already working for another developer on the world's tallest building: the Burj Dubai.

"How tall is it?"Trump wanted to know.

"I can't tell you," Smith said. "It's a secret."

"Well, I'd like to get involved with that," an excited Trump said. "We could call it the Trump Burj Dubai and make a killing!"

There ends the saga of Donald Trump's attempt to build his Xanadu. Well, for the time being. He has not weighed in on the architecture of the White House, so far as I know, but one can imagine a President Trump surveying his domain and concluding that America needs the tallest, most luxurious, best presidential palace—in the midst of a city where the tallest residential building is a loser-sized 177 feet. "D.C. is the capital of the mightiest empire in human history," writes Matthew Yglesias. "In no universe should Richmond have more tall buildings than the District of Columbia."

Where better to Make America Great Again?