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Insights into Character: The New Obama Portraits

Richard Speer

Politics and aesthetics converged in the White House on September 7, when Barack and Michelle Obama returned together for the first time to the executive mansion in which they once resided. The occasion was the unveiling of their official portraits, commissioned by the White House Historical Association. The occasion was long overdue, as these unveilings are traditionally hosted by the succeeding president. If that president belongs to the opposing party, the occasion becomes a rare opportunity for bipartisan bonhomie. Gerald Ford was welcomed by Jimmy Carter, George H.W. Bush by Bill Clinton, and George W. Bush by Obama. 


Not so with the administration of a certain orange-tinted paragon of pique, who refused to schedule the Obamas’ fête during his tenure. This comes as no surprise from a man constitutionally averse to bipartisan events such as the White House Correspondents’ Dinner, the Kennedy Center Awards, and for that matter, his democratically elected successor’s inauguration. So the unveiling waited until this month, with Joe and Jill Biden greeting the Obamas with a warm “Welcome home.” The former president’s remarks, standing in front of his portrait, were themselves a bittersweet reminder of the eloquence, dignity, and poise we lost the instant Donald Trump replaced him in the Oval Office.


Robert McCurdy, “Untitled,” 2018, oil on canvas, 73 x 68".

Courtesy of White House Historical Association/White House Collection

As for the paintings themselves — Mr. Obama’s by Robert McCurdy, Mrs. Obama’s by Sharon Sprung — they were immediately and inevitably compared to the better-known portraits that debuted in 2018, painted respectively by Kehinde Wiley and Amy Sherald for the National Portrait Gallery. Most media coverage of the new images has parroted a simplistic assessment of them as more stylistically traditional than the earlier ones. I disagree. 


Sharon Sprung, “Michelle Obama, Former First Lady

of the United States,” 2022, oil on panel, 44 x 36”.

Courtesy of White House Historical Association/White House Collection

True, on the face of it, Wiley’s florid, Henri Rousseau-like background and Sherald’s uncanny grayscale handling of her sitter’s skin may seem far removed from McCurdy’s plain white background and Sprung’s dusty rose and caramel depiction. But that observation is superficial and facile. The paintings have more in common than apart. Wiley’s and McCurdy’s Obama, though the former sits and the latte stands, are both cool cucumbers, implacable, strong, and steely, both portrayed with a high degree of realism. If Wiley’s foliage telegraphs a certain surrealism, McCurdy’s hermetic white is equally unnatural, reminiscent of Richard Avedon’s immaculately neutral backdrops. Both painters, I would argue, take equally conceptualist tacks, the former in recontextualizing hip-hoppers as Roman and Baroque heroes, the latter by virtue of his pedantic insistence on the primacy of “the gaze,” which he construes as an incongruously affectless, yet meaningful, encounter between portraitist and subject. McCurdy’s means of engendering such an encounter is to paint his subjects before stark white backgrounds. It is an unintended symbolism, then, but one worth noting, that our nation’s first black president stands before an unexpectedly charged white background — a superimposition all the more striking given the encouragement Obama’s successor gave to white supremacists. This background, then, is historic as well as chromatic.

Presidential portraits are a genre unto themselves, and one I find fascinating. I saw the Wiley and Sherald paintings in the National Portrait Gallery in late summer 2019 and was taken by the museum’s permanent collection. My favorites were John Singer Sargent’s imposing Teddy Roosevelt, the loose, quick brushstrokes of Elaine de Kooning’s John F. Kennedy, and believe it or not, a disarmingly humanized Richard Nixon by none other than Norman Rockwell. (Tellingly, Rockwell later groused that Nixon was “no fun to paint” because of his “mean eye” and jowls, and confessed he painted the president as more handsome than he really was.) First Lady portraits can also offer insights that are both flattering and unflattering. 

In 2018 at the Ronald Reagan Presidential Library in Simi Valley, I saw Aaron Shikler’s 1987 portrait of Nancy Reagan (actually a copy of the original, which hangs in the White House) and was impressed how the artist conveyed Mrs. Reagan’s icy elegance atop a column of red-hued haute couture — an aloofness thrown into relief by her positioning before a backdrop of dark wooden panels, compositional devices that isolate the figure while also evoking Mrs. Reagan’s isolation as a Hollywood transplant never fully accepted into Washington society.

It is natural to want to remember our leaders through portraiture. The gradually aging visage of Queen Elizabeth II, rendered by a succession of British artists, adorned the currencies of the United Kingdom and the Commonwealth for seventy years. Soon the U.K.’s treasury will commission a new portrait of a new king, and already details are being parsed, including which direction Charles III’s profile will face. In the United States, it’s hard to imagine our one-dollar bill without the semblance of George Washington, although it’s easier to imagine our twenty-dollar bill with a portrait of Harriet Tubman instead of Andrew Jackson, now that the Biden administration has restarted the push to make the switch (a push stalled by Trump in one of his many racist dog-whistles). Portraits of presidents and first ladies may not have much direct bearing on our daily lives, but at their best they offer insight to the characters of those who shape our destinies.

The Obama portraits have joined a pantheon of images that will long outlive their subjects and may convey something of their high-mindedness and graciousness to our descendants, should our American experiment endure. Donald and Melania Trump’s portraits will also hang in the White House eventually, and one might be forgiven for musing what shade of orange will be chosen for his face, or whether Melania will be immortalized not in her inaugural gown but in her “I REALLY DON’T CARE, DO U?” jacket.


John Singer Sargent, “President Theodore Roosevelt,” 1903, oil on canvas, 58 x 40”. Courtesy of the White House Historical Association/White House Collection

Norman Rockwell could flatter Richard Nixon all he wanted, but the man with the “mean eye” and even nastier soul could not escape his country’s judgment; nor will Trump. Paint can lie and pulchritude reside in the eye of the beholder, but character and reputation are the province of history.


Elaine de Kooning, “John F. Kennedy,” 1963, oil on canvas, 102 1/2 x 44”. Courtesy of the National Portrait Gallery, Washington D.C.


Aaron Shikler, “Nancy Reagan,” 1987, oil on canvas. Courtesy of White House Historical Association/White House Collection


$20 face conceptual design with refined Harriet Tubman portrait.

Original image of Harriet Tubman courtesy of the Ohio History Connection

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