Trump’s Freedom 250 gives the founders an AI glow-up

Phyllis Wheatley is the only black woman featured in the Freedom 250 gallery. Her sky-colored dress stands apart from the uniformly darker blue garb in the other portraits.
(CNN) — Meet Dr. Benjamin Rush, the illustrious physician, academic, and Founding Father, as presented in the gallery of founders on the Freedom 250 website. His brow is porcelain-smooth and suffused with light, his locks glossy and curled, his nose straight and regular. He stands upright with his head slightly tilted, an index finger laid coyly against his cheekbone, looking directly at the viewer with methylene-blue eyes and a faint smile.
Paintings of Rush made in his lifetime depicted a man with flat hair and long, pinched features. An 1812 portrait by Thomas Sully presented him with a long, downturned nose and corners of his mouth to match, leaning on one hand at his desk and gazing over the pages of an open book.
The luminous, unreal Rush of Freedom 250 — the nonprofit spun up to lead the Trump administration’s efforts to take control of this year’s semiquincentennial events — looks like some other person altogether, from some other era. Or like no person from no time at all: A digital watermark on the image identifies it as the product of Google’s generative AI.
And he has plenty of company. To educate the public about the semiquincentennial, Trump’s anniversary organization has given all of the dozens of Revolutionary War-era figures in the gallery similar artificial glow-ups, or entirely fictitious faces.
The men’s hairstyles, and often their physiognomies, frequently seem to converge on the canonical portrait of George Washington by Gilbert Stuart. They wear overwhelmingly similar clothing and repeat the same set of poses over and over. And they share the AI watermark.
One small subsection of the gallery features four “Ladies of the Revolution,” generally swan-necked, snub-nosed, and dressed in near-identical clothes. These women, the public historian Isabelle Roughol noted this week in a widely viewed video, are particularly anachronistic. Dolley Madison, shown as an adult woman, would have been 8 years old at the time of the revolution. (Martha Washington, called “Lady Washington” and a key figure of the war, is notably absent.)
The portrait of Abigail Adams seems especially odd. For a woman who died in 1818, her face seems slightly too taut, her eyes slightly too wide, her skin slightly too bright. She looks like Anne Hathaway playing Adams in a biopic.
What she doesn’t look like are any available images of Abigail Adams. Consider Benjamin Blyth’s 1766 pastel portrait of a 21-year-old Adams completed just after her wedding to John Adams. Her face is almond-shaped with a slightly hooked nose and a thin upper lip. The portrait in the digital gallery squares off her face and provides an artistic rhinoplasty and lip filler. Her brown eyes have also been supersized to the point where she resembles an anime character.
Many of the other images appear to have had roots in real portraits, but their details seem to have been changed to be more uniform and align with a more corporate vision of American history, said Zara Anishanslin, a historian at the University of Delaware and author of “The Painter’s Fire: A Forgotten History of the Artists Who Championed the American Revolution.”
The Freedom 250 versions of the founders stand in front of neoclassical columns and banisters, decorative features favored by the current Trump administration but not common in Revolutionary-era portraiture. Some of the subjects’ repeated poses are also anachronistic. Some have their arms crossed over their chests or fingers cradling their chins in thought — or, in Rush’s case, a combination of both — neither of which would have been standard stances for an 18th century portrait sitter, Anishanslin said.
“It’s almost like modern CEO imagery that’s being grafted onto these 18th century founders,” she said.
In a particularly eerie feat of conformity, every man in the portrait gallery wears a near-identical blue coat, even though portraits from their lifetimes feature them dressed in an assortment of brown, black, gray and other-colored garments. Benjamin Franklin’s blue-coated portrait looks like a jawline-tightened version of an 18th century portrait by the French artist Joseph Duplessis, which featured Franklin in the unadorned gray coat he deliberately wore to contrast his country’s republican simplicity with the pomp of France, Anishanslin said.
The cut of the shoulders of the coats, and the cravats the AI-generated founders wear with them, are more associated with 19th century fashions than 18th, according to Anishanslin. And there are other oddities: Thomas Jefferson appears to be closely copied from his official portrait by Rembrandt Peale, but his eyes — ambiguously colored in real life — have been switched from Peale’s dark brown to a clear blue (Jefferson’s pose also now includes a hand pensively stroking his chin). One man after another sports the puffed-out sides of George Washington’s hairstyle, sometimes accompanied by a glimpse of Washington’s characteristic queue, or ponytail.
Whole rows of them — Francis Lightfoot Lee, George Clymer, George Read, alphabetically by first name — simply resemble repeated images of Washington. Clicking on each one brings up a capsule biography and a semi-faithful version of an authentic portrait; the effect is as if the user were turning off a George Washington face filter.
All of the men’s portraits also share something else: a SynthID watermark. The digital marker is embedded in media created using Google’s AI products as a way to help differentiate between real and fake images. The women’s portraits did not contain SynthID watermarks, but an AI detection tool flagged them as containing synthetic elements.
The only figure, man or woman, not shown wearing identical American-flag blue is the poet Phillis Wheatley, who wears a pastel shade and who also happens to be the only Black person featured in the gallery.
“That light blue gown really sticks out,” said Anishanslin. “It’s meant to set her apart from the others.”
The web gallery is designed to be an educational resource. Each capsule biography offers a short video created in partnership with the conservative media organization PragerU. The videos begin with a relatively historically faithful portrait of the person — which then rotates to become an animated simulacrum talking about the role that person played in the country’s founding.
The glossy uniformity of the images also serves a political purpose, Anishanslin said.
“The message is clearly being sent that the founders were a united group of people and that they were united in their ideologies and politics in creating the nation,” she said. “And that narrative just isn’t true.”
Historical accuracy isn’t the only rubric that art is judged by, though. Anishanslin pointed to the painter Emanuel Leutze’s 1851 depiction of George Washington crossing the Delaware River during the Revolutionary War.
“It’s inaccurate in several ways, but it was heroicizing a moment,” she said.
In the 1980s, Hollywood started collaborating with the Department of Defense on films that would paint a more triumphant, patriotic portrait military compared to the critical movies made in the shadow of the Vietnam War. For an administration fixated on promoting a romanticized triumphal past — particularly on romanticizing the inequities of the past — and for a president obsessed with AI art, the gallery of yassified figures of the Revolution signals a desire to return to an era of American prestige and pride.
Like that 1851 depiction of Washington, these portraits smudge the details of history in favor of a fantasy. Jefferson’s blue eyes, the covered chests of the women — a contemporary style likely based in morality; 18th century portraits usually left the upper chest exposed, as Dolley Madison’s is — and the matching suits all tell a story contrary to history.
The production is similar to something like “Bridgerton,” Anishanslin said. Rather than an accurate depiction of what life was like in the Regency era, “Bridgerton,” with its inaccurate costumes and tightly cinched corsets, appeals to viewers’ “cultural imagination.”
“This is different,” she said. “‘Bridgerton’ is fun and pop culture and entertainment, but this is purporting to be a history site.”
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