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Trump’s Colorado Painting & Other Presidential Portrait Stories

March 26, 2025
A painting of Theodore Roosevelt posing at the base of a stair, placing his hand on the balustrade.

Theodore Roosevelt by John Singer Sargent

A portrait of Donald Trump hanging at the Colorado State Capitol building has been removed after many people online decided the president’s depiction was amusing and unflattering.

Apart from when they are first unveiled, presidential portraits don’t often receive much attention in the news. Nowadays, former presidents will usually have multiple portraits done, with the National Portrait Gallery (NPG) commissioning a painting for their American Presidents exhibition. The White House Historical Association also curates their own collection of presidential portraits. While they may seem like rather simple paintings, many of them have fascinating stories revealing different aspects of the subject and the painter. 

Theodore Roosevelt

Teddy Roosevelt was a man of action. His official portrait, though static, serves as an example of this. Finding himself unsatisfied with an earlier portrait, Roosevelt hired renowned painter John Singer Sargent. The president and the artist spent a good amount of time together, with Sargent following Roosevelt all around the White House, making sketches from every conceivable angle and in every form of light. However, the painter simply could not find a suitable setting or pose for the portrait. Sensing this, Roosevelt paused to address the artist shortly before ascending a set of stairs, placing his hand on the balustrade. Hit with inspiration, Sargent decided this was exactly what he would paint: a president constantly on the move, taking a brief moment to address the viewer. However, Roosevelt’s rigorous schedule meant that the president could only pose for Sargent for half an hour each day, right after lunch. Roosevelt reportedly liked this painting far better.

Bill Clinton

While Bill Clinton’s official White House portrait by Simmie Knox shows the president in a very dignified pose, standing before the Resolute Desk in the Oval Office, the painting commissioned by the NPG is slightly more scandalous. The gallery commissioned the portrait from Nelson Shanks. However, it seems the artist may not have been the president’s biggest supporter because he decided to include a nod to one of the biggest political scandals of the 1990s. The Shanks portrait shows the president in the Oval Office’s fireplace with his hands on his hips. It’s far more casual than the Knox portrait, almost like you’ve caught him in the middle of something. However, the president is not in the center of the painting; he is slightly on the right-hand side. The left-hand side would be unremarkable if it weren’t for a noticeable shadow coming across from just outside our view. Shank later said in a 2015 interview that the shadow represents the Monica Lewinsky scandal that plagued Clinton’s presidency during his second term. Shank admitted that he modeled the shadow based on the shadow cast by a mannequin wearing a blue dress, a reference to the infamous dress Lewinsky war that later served as proof of an affair between the president and the White House intern. It is one of the few portraits kept from display at the NPG.

A portrait of John F. Kennedy, looking down with his arms crossed.

John F. Kennedy by Aaron Shikler

John F. Kennedy

The portrait of John F. Kennedy by Aaron Shikler is the president’s official White House portrait. Jacqueline Kennedy commissioned the painting in 1970, making it one of the few posthumous presidential portraits. Jackie Kennedy intentionally asked for the picture to stand out among others by not having her late husband look in the direction of the viewer. She admitted that she did not want to see her late husband as he had been shown before, “with the bags under his eyes and that penetrating gaze. I’m tired of that image”. Instead, Shikler shows Kennedy with his arms crossed, looking downward as if lost in thought or possibly melancholy. The artist stated that he drew inspiration from images of Ted Kennedy at the president’s funeral. Even with Kehinde Wiley’s colorful portrait of Barack Obama, Shikler’s painting remains one of American history’s most distinctive presidential portraits.

Franklin D. Roosevelt

The official White House portrait and the NPG-commissioned portrait are often the only paintings worth mentioning in terms of presidential portraits. For Franklin Roosevelt, Frank Salisbury painted the White House portrait in 1947. The president’s NPG portrait by Douglas Chandor was originally intended as a study for a larger group portrait along with Winston Churchill and Joseph Stalin commemorating the Yalta Conference. However, there is another painting worth mentioning. In April 1945, the president’s longtime mistress, Lucy Mercer Rutherfurd, reached out to her friend, the portraitist Elizabeth Shoumatoff, to paint the president’s picture while he stayed at his house in Warm Springs, Georgia. Shoumatoff agreed to have the president sit for her over two days starting April 12th. The artist completed Roosevelt’s face and parts of his torso before the president began experiencing headaches. This was the cerebral hemorrhage that later led to Roosevelt’s death at around 3:30pm that same day. Shoumatoff was later involved in a cover-up since the public was unaware of the president’s affair with Rutherfurd. The portraitist intentionally omitted any mention of Rutherfurd when she spoke to members of the press. Shoumatoff’s unfinished portrait now hangs at the house in Warm Springs where it was created, serving as a retrospectively somber depiction of Roosevelt’s last days. The artist was later commissioned as a presidential portraitist a second time when Lyndon Johnson sat for his official White House portrait.

Donald Trump

The Colorado State Capitol building hosts a small gallery of presidential portraits. Unlike the paintings at the NPG, the Colorado Capitol paintings are somewhat uniform, showing bust-length portraits of every American president against a dark, gray-green background. The Colorado legislature unveiled Trump’s portrait in the summer of 2019. The artist, Sarah Boardman, stated that she intended for the president to appear “thoughtful, non-confrontational, not angry, not happy, not tweeting”. However, nearly six years later, the painting has gained the attention of the president’s critics and the president himself. Many online comments have remarked that the portrait makes the president appear chubby and docile. Trump also complained, claiming that the painting was “purposefully distorted”. The Colorado state legislature’s executive committee promptly issued a statement calling for the portrait’s removal. Trump initially blamed Colorado’s Democratic governor, Jared Polis, for displaying a seemingly unflattering representation at the capitol. However, curating paintings in the capital building is not part of the governor’s job. Trump has already received a good deal of criticism for his complaints about such a small issue as a painting in a state capitol building. Social media accounts online have called him “a petty, insecure baby” as well as “the most fragile, sensitive snowflake in history”.

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