It's not clear exactly who this man is, but he might as well be popping off a selfie or thumbing through his news feed. He seems to gaze into the handheld device in such a way that renders all-too-familiar today, as if he's just read a bad tweet or recoiling from a Trump-related push notification from the Times. He would almost look unremarkable, if only he and the world around him existed at any point in the past decade.

This story is part of DOUBLE TAKES , a Motherboard meditation on the tech-time continuum that reinterprets old art through the lens of modern digital anxieties.

Adding a layer of intrigue to it all is the fact that Romano's mural is focused on one William Pynchon—that's him at center, wearing pink—who wrote The Meritorious Price of Our Redemption, the first book ever to be banned (and subsequently burned) on American soil, and who just happens to be the earliest colonial ancestor of elusive living novelist Thomas Pynchon.

It's a question that keeps me coming back to Romano's "Settling." The man is found in the first of four mural panels that comprise the artist's retelling of New England history , which falls under the care of the United States Postal Museum and currently hangs in the Commonwealth of Massachusetts State Office Building (formerly the Central Post Office) in Springfield.

In other words, what the man in the painting holds simply cannot be an iPhone.

Flash forward, and we can pin the entrance of the portable cellular telephone into the historical record to a precise date— April 3, 1973 —nearly four decades before Steve Jobs, in 2007, revealed the so-called "one device," now arguably the best-selling product in history.

But the multi-part, New Deal-era mural the man occupies, titled "Mr. Pynchon and the Settling of Springfield," pre-dates the iPhone by seven decades. Completed in 1937 by the late Italian semi-abstract painter Umberto Romano, "Settling" is loosely based on actual events that occurred around a pre-Revolutionary War encounter between members of two prominent New England tribes, the Pocumtuc and Nipmuc, and English settlers at the village of Agawam in present-day Massachusetts in the 1630s, some 200 years before the advent of electricity.

Whatever it is, I just can't stop looking at him. The longer I look, the closer his profile appears cut along what is perhaps the defining gesture of the digital age, a pose made all the more curious considering the obvious: that both the painting and what's painted came many generations before the digital age. It's uncanny.

Or, maybe it has to do with confronting a tendency to project present-day anxieties onto the past through the miasma of a historically white-washed genocide narrative.

Maybe, despite working for a tech publication, it's because I am too regularly overwhelmed by even basic consumer technologies, including (especially) my iPhone, a composite of dredged-up Earth and backbreaking labor .

Maybe I've read too much of the latter Pynchon, who was born in—wait for it—1937, the same year Romano finished "Settling," and whose paranoid fictions, a noted Pynchon scholar told me in 2012, don't "necessarily present technology as a good thing."

"To put it in the kindliest possible terms, Romano's so-called 'abstract' aesthetic was willfully ambiguous," Crown told me over email. But it could very well be, he added, that the man quite literally sees himself in the handheld object, looking back at him.

My introduction to the man came recently by way of New York City-based writer and historian Daniel Crown, who published an illuminating essay on William Pynchon in The Public Domain Review in 2015. Crown's piece makes one passing mention (in an image caption written by a PDR editor) to the object the man holds, noting how it bears a striking likeness to a smartphone. Romano, who died in 1982 at the age of 77, appears to have made no remarks specifically about the man; whatever clarity the artist could've offered he likely took with him to the grave. Crown's nod to the sitting man, near as I can tell, is the first and only such reference to date. I figured I'd start by reaching out to him.

"When Romano painted the mural, Americans were obsessed with the 'noble savage' trope," Crown told me. "Given the scene's focus on the founding of Springfield, Romano, in reductive fashion, was probably trying to capture the introduction of modernity into a curious but technologically stunted community, which was instantly bewitched by Pynchon's treasure trove of shiny objects."

The shiny object in question? He thinks it's a mirror.

This hunch tracks with the location of the man's figure inside a crate full of what look like ceramic jugs, amid a scene full of trade goods. There's reason to believe, then, that what the man is examining is not an Indigenous object, but rather of European origin, like mirrors, which were presented often in such exchanges. The way the man holds it up, if indeed he's looking at his own face reflecting back at him, would certainly make sense.

When Europeans introduced such reflective devices to Indigenous peoples in the 1600s, "many Native nations incorporated [mirrors] into tribal aesthetic and cultural contexts," as Indigenous art, fashion, and design expert Dr. Jessica R. Metcalfe wrote in a 2011 blog post about mirrors in Indigenous culture. In that post, Metcalfe, herself of the Turtle Mountain Chippewa of North Dakota, pulls from The Arts of the Native American, a 1986 book by Native art specialist Edwin L. Wade, who reflected on the differences in mirror usage among Indians and European settlers around this time:

For Native Americans, mirrors were symbols of wealth and prestige. They were commonly mounted in dance batons or other objects of ceremonial regalia, since it was their light-reflective property, not their ability to reflect images, that was considered important.

In this view, it could be said Indigenous peoples, who likely used the image-reflective properties of pools of water as needed before Europeans showed up, turned the colonialist notion of mirrors inside out.

But even then, we could still be looking at a rendering of the very moment that foreign technology first bewitched one individual.

"There are so many things wrong with this image that it's hard to know where to begin."

Another possible theory extends the idea of an outside, potentially corrupting influence. If not a mirror, what the man holds might be a pocket-sized edition of a religious text, Crown said. "One of the gospels or maybe Psalms," he added. "These did exist at the time and were roughly the same rectangular shape."