Why Trump’s East Wing Teardown Messed with Our Heads

This is basic autocratic playbook stuff.

The East Wing of the White House. Via Getty images

by Rich Herschlag

In the dead of a cold dark night in January 1985, four aging single-room occupancy buildings at the outskirts of Manhattan’s Hell’s Kitchen were demolished with no permit, no notice, and without even first turning off the gas, water, or electricity. In the immediate aftermath of this citywide outrage, the Manhattan District Attorney filed criminal charges against various culprits. At the top of the list was Harry Macklowe, a developer well known for cutting corners or, in this case, cornerstones. At the time, the city had proposed a moratorium on demolishing SROs—which essentially served the homeless or indigent—and it so happened that moratorium was to kick in two days after the middle-of-the-night impromptu teardown.

The case was settled in May of that same year with a misdemeanor, no jail time plea for John Tassi, Vice President of Macklowe’s real estate firm, and a $2 million slap-on-the-wrist fine for Macklowe himself, with the money going to fund new SROs. For Macklowe and company you could say it was lesson learned—the lesson being you can brazenly break dozens of laws and endanger public safety if in the end you can cut a relatively modest check that can be written off as a business expense.

But that was an old lesson simply reapplied again and again whenever needed. In 20^th century urban cowboy New York, as in most large American cities, developers learned from developers and criminals from criminals, and there was plenty of cross-pollination. In 1965, Donald Trump’s father Fred bought Brooklyn’s legendary Steeplechase Park with the intention of demolishing the landmark to build a residential development. Rather than subject himself to a cumbersome multi-tiered application process he rounded up some local troublemakers and had them destroy the park’s famous Pavilion of Fun as in some vapid reality show decades ahead of its time.

Fourteen years later, seeking to build has phallic iconic Trump Tower on the site of the old Bonwit Teller building at 56^th Street and Fifth Avenue in Manhattan, Fred’s insatiable son Donald reneged on his promise to preserve a pair of 15-foot bas-relief sculptures over the store’s main entrance and donate them to the Metropolitan Museum of Art. Instead, in order to save a grand total of $32,000 and present his middle finger to the city he loved so dearly, the Donald on June 5, 1980 had a demolition crew jackhammer the sculptures right off the building. For these chutzpah-driven acts of utter disregard for both law and decency the Trumps paid not even Macklowe-worthy penalties.

Here in an increasingly lawless, yahoo 2025 America that’s starting to make mid-20^th century New York look like Andy Griffith’s genteel TV pretend town of Mayberry, I tried to make sense of the over-the-top outrage expressed by numerous friends, family members, and center-left social media enthusiasts.

While for me, a native New Yorker who later served as Manhattan Borough Engineer and sparred with Trump and his cohorts, the East Wing teardown was not only part and parcel of a very well established M.O. but bordering on predictable, for many folks around me it triggered a massive visceral reaction and represented a crossing of some sort of new Rubicon of derangement.

Because I can’t leave bad enough alone I decided to spend some otherwise quality time figuring out why. And I realized this was a brilliantly multipronged act designed to hit a bunch of raw nerves all at once. Here is my quick breakdown.

It Was Highly Tangible

There was no abstraction here. No reinterpretation of the Monroe Doctrine necessary. No application of graduate school level econometrics required. No moronic words to parse during a softball 60 Minutes interview. This vile criminal act was not only as in-your-face as it can get but also produced the kind of jarring trail of physical destruction usually left to tornadoes, category 5 hurricanes, and magnitude 8.0-plus seismic events.

It’s What Dictator’s Do

The Hitlers, Mussolinis, Stalins, and Caligulas of the world have long sought and achieved brutal, grotesque, unredeemable dominion over the physical environments of their subjects. This is basic autocratic playbook stuff. It is the desire to instill fear masked as architectural predilection. When it comes to demolition without warning, just know this—Next time it could be you.

No Plans to Leave

While there is reportedly a three-year buildout estimated to construct a 90,000 square foot ballroom for the next occupant of the White House, the odds that Donald J. Trump is getting his house in order for Gavin Newsom or Marjorie Taylor Greene is exactly zero. The Orange Abomination is telling us in not-so-veiled smoke signals formed by demolition dust that three, five, ten years from today it will still be 47 dancing the two-handed masturbation jig in that sprawling gold-plated shrine to political corruption.

It’s a Metaphor for What He’s Doing to the U.S.

If you watch the demolition video a few times you can see all sorts of things. The third time I watched it I saw the Constitution go up in flames. The fourth time I swear I saw the ghost of Teddy Roosevelt gently sobbing. The fifth time was a real Rorschach test in which I made out the rough image of my progressive wife and rightwing brother-in-law trading insults at last year’s Thanksgiving dinner. Next viewing I’m going to smoke some peyote and see what happens.

It’s a Particularly Grifty Grift

The East Wing teardown was nothing if not a mobbed-up act worthy of a Tony Soprano. More tax free laundered dark money will be moved through that make-believe ballroom than the Trump meme coin after a Zoom call with Argentine President Javier Milei.

Real People Struggle to Get Permits

As a consulting engineer I’ve spent over half my adult life helping beleaguered home and business owners desperately trying to obtain a permit. In some municipalities it’s gotten to the point where a fresh coat of sky blue paint on your kid’s bedroom wall requires a zoning variance. Unless, of course, you’re an A-hole, demonic, renegade head-of-state, in which case you can nuke the People’s House during a round of golf and a hand job from Laura Loomer.

It’s an Outrageous Distraction

Air traffic controllers calling in sick. Forty million Americans facing potential starvation. Recreational detonation of Venezuelan fishing boats. The de facto dissolution of Congress. The pedophile files. Endless meritless prosecution of public servants who fail to bow down. Extortion of top universities. Elimination of cancer research. Extermination of impoverished people worldwide in the name of saving pennies. Invasion of U.S. cities by U.S. armed forces. Eradication of official employment data. The reboot of nuclear testing. The hits just keep coming. Let them eat cake and ponder the desecration of Jackie Kennedy’s garden.

It’s Batshit Crazy

Notwithstanding all the arguably tactical aspects discussed herein, the whole teardown was obviously just nuts because, like, no one does that. Which leads us to the final and most disturbing point.

We Know Something Worse Is Coming

With Trump, every horrible reprehensible despicable villainous act is a prelude to another horrible reprehensible despicable villainous act. We never know what will be, when it’s coming, or how he will turn it into another stab at a Nobel Peace Price, but we know it’s coming and that when it arrives we’ll feel blindsided at best and castrated at worst. I can’t print what I’ll really want to do upon receiving the next Trumpian kick in the groin. So I’ll see you right here and we’ll bitch about it.

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