Is Trump’s Skyline Drawing Really That Bad? An Investigation

Trump's seemingly horrible drawing of the New York City skyline just sold for almost $30,000. We decide to draw our own to see if we could do any better.

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Jul 28 2017, 8:45pm

Images via Getty and Nate D. Sanders Auction

The political news cycle moves at such a rapid pace, sometimes little gems simply get lost. So if you haven't seen the president's incredible 2005 drawing of the New York City skyline, which sold for $29,184 at auction on Thursday, here it is and you are welcome!

If your reaction to this image is anything like mine, you're probably thinking: Wowza! That's a shit rendition of the New York City skyline. A toddler could do better, and honestly I expect more from a New York real estate magnate. Then again, this is Donald Trump we're talking about. Of course it's a low-quality product that sold for an unimaginably high price.

But I am a journalist, which means that in order to truly understand how bad this drawing is, I must investigate. What does the average sketch of the New York City skyline from memory look like? We can't all be this guy:

For comparison's sake, I asked the lovely staff of VICE.com to draw the New York skyline from memory to see if they could do better than Trump. Here's what we discovered. Here's what we learned about ourselves, and also, what we lost.

Mike Lee Pearl, 32, Staff Writer

"I think the Brooklyn Bridge is the coolest thing in the skyline (arguably), and that's why I used my memory of a Beastie Boys poster as the source of the image. If I had it to do again, I would put windows on the buildings."—MLP

Winner: Mike
Mike's decision to include the Brooklyn Bridge was incredibly smart, because it instantly makes the drawing recognizably New York. Great job, Mike! You totally kicked Trump's ass.

Harry Cheadle, 30, Senior Politics Editor


"My process was to try to draw all the important buildings and fill in the gaps with rectangles. I feel like I did better than Trump at least."—HC

Winner: Harry, by the skin of his teeth
This barely beats Trump's attempt at the skyline, but because the standards were so staggeringly low, Harry managed to pull through.

Eve Peyser, 23, Staff Politics Writer

"I am a lifelong New Yorker and I studied art in college, so I'm admittedly ashamed of myself for not doing a better job. The standard is extremely low, but I do think mine is considerably more accurate than Trump's, and unsurprisingly, less phallic."—EP

Winner: Eve
This is my drawing, so I apologize for the inherent bias that went into this decision. Like everything I do, my drawing is endearing, yet fundamentally flawed. Also, like everything I do, it's far superior to Trump.

Allie Conti, 27, Senior Writer

"For my picture, I added lots of line detail to obscure the fact that I don't know a single landmark in the New York skyline besides the Empire State Building (which I only remembered because I overheard someone joking that Trump forgot to include it in his sketch). Overall, I feel like Trump's drawing is the one thing I can't knock him for. Who the hell knows what the cityscape looks like from memory? Perhaps the sole difference between his artwork and mine is that I don't expect $30,000 for something I drew in five seconds on some computer paper."—AC

Winner: It's a tie.
I appreciate how Allie has made what I believe to be the Empire State Building (far right) simultaneously phallic and yonic. Unfortunately, her drawing is no more recognizably New York than Trump's. To her credit, it's certainly not worse than Trump's.

Jonathan Smith, 33, Editor-in-Chief

"When drawing my picture of the New York skyline I thought mostly about New York and how it looks from afar. I think my illustration is very good and most people probably would mistake it for an actual photo of the New York City skyline, even though it's actually a drawing."—JS

Winner: Jonathan
Even though Jonathan is my boss and has the ability to decide my future at this company, I promise I'm being sincere about this. Despite his facetious caption, Jonathan actually did a pretty good job at representing New York City. Compared to Trump, of course, but he also surpassed Allie and Harry in this brutal challenge.

Brian McManus, 43, Special Projects Editor

"This was incredibly difficult and self-deflating. We have a goddamn view of the skyline from our office. I look at it a few days a week, and I still couldn't manage this. That's mostly due to my atrocious drawing skills, which I've come to find have atrophied to the point of being nearly non-existent. I was so embarrassed by my effort I put water towers on every building to make it seem as though I didn't really take seriously. I did. (Hope no one is reading this.)"—BM

Winner: Trump
Brian is the first VICE staffer who was unable to best Trump in the skyline drawing competition. Sorry Brian. I like you better than most of my co-workers, so this decision pains me to make.

Lauren Messman, 25, Associate Editor

"Because my artistic skills are basically at a kindergarten level, I decided to go full Thanksgiving arts-and-crafts day with it and trace my hand as the skyline. It may not accurately reflect the height of each building in the New York skyline, but unlike Trump's drawing, I think mine captures their individuality. It also took me three minutes. Can I have $30,000 now?" —LM

Winner: Lauren, I guess
I admire Lauren's creativity, but doing the hand-drawing was a cop out in that it makes it much harder to seriously compare her skills to Trump's. She's certainly creative, I will give her that, but not much more.

Jamie Lee Curtis Taete, 32, Executive West Coast Editor

"I haven't spent enough time in NY to do an accurate version of the skyline from memory, but I have seen enough episodes of Frasier to do a passable version of the title card. As with all aspects of my life, I'm hoping that making a joke will cover up my intellectual shortcoming."—JLCT

Winner: Jamie
Is it too early too say that Jamie hands down wins against the whole VICE staff? Of course not, especially because I wrote this article so I know what's to come. Jamie's drawing is the best on both a technical and compositional level. (To remind you, I minored in art at Oberlin College, so I'm a certified expert.) I'd also like to note that Jamie is one of two participants in this competition who is not based in New York City. Praise Jamie.

Janae Price, 23, Editorial Assistant

"I don't think my drawing looks horrible, but it's definitely not accurate. When drawing the skyline, I tried to copy some pictures I googled as closely as possible, but it wasn't as easy as I originally thought it would be."—JP

Winner: It's a tie.
After specifying that in order to partake in this little project, you could not google any reference photos, Janae asked if she could cheat. I had to oblige her because, hey, this is Trump's America. Anything goes! Unfortunately for Janae, not even breaking the rules could help her best Trump in this competition. I'd say they are about even. I would've called it for Janae had she not cheated, but that's not how it went down.

Peter Slattery, 23, Social Media Editor

"Besides the super obvious famous buildings, it's pretty hard to remember a lot of the specific skyscrapers in NYC's skyline. Also, I had to get back to work so I just gave up on drawing the Chrysler Building."—PS

Winner: Peter
On an aesthetic level, I'm a huge fan of MS paint, so I commend Peter on his choice of medium. It's a more sophisticated drawing than Trump's, and better resembles the New York skyline. However, I can't vouch for its realism: The sun does not and never will wear sunglasses.

Alex Norcia, 26, Copy Editor

"It's a busy picture I drew, one that captures the rush and excitement and possibility of residing in New York. It is, in my mind, a failed success. I used a pencil here as a symbol of erasure—as a way to encapsulate the impermanence and uncertainty of life, because even if you live here, you're going to die one day."—AN

Winner: Alex
Alex is a creative thinker, so he opted to capture the spirit of the Big Apple instead of accurately portraying the skyline. That being said, it resembles New York more straightforwardly than Trump's drawing, so I applaud that. He did what he could.

In total, eight VICE staffers were able to draw a better skyline than the president, while the other three either tied or were defeated by him. However, none of us built our careers in New York real estate, so we were all at an automatic disadvantage.

What does all this prove? Donald Trump is bad at drawing, and it doesn't matter. All he has to do is sign his name, and boom! A shitty drawing on a scrap of paper is suddenly worth $30,000. This leads me to believe what I already know: Any economic system that values that garbage drawing at the price of a new sedan is an insanely flawed economic system. As per usual, down with capitalism.

Follow Eve Peyser on Twitter.

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