Italian artist Umberto Romano painted the mural above in 1937 in the original Springfield, Massachusetts post office, now the Commonwealth of Massachusetts State Office Building. Titled "Mr. Pynchon and the Settling of Springfield," it's actually the first in a series of murals telling the story of Springfield's history from 1636 to 1936. More details at the Smithsonian National Postal Museum site. But if Romano painted this in 1937, how come the Native American in the bottom middle appears to be staring at a smartphone? From Brian Anderson's riff on the matter in Vice:
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.
"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.
"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.
"Do We All See the Man Holding an iPhone in This 1937 Painting?" (Vice)