John F. Kennedy: A Rare Signed Original Painting by the 35th U.S. President. Courtesy of Heritage Auctions.

Two presidential artworks went head to head at Heritage Auctions Texas, with John F. Kennedy besting Donald Trump, the former’s oil painting fetching $162,000 as compared to just $20,000 for a sketch by the reality TV star-turned-politician. Both works feature skylines. The Kennedy piece is believed to depict a town in the South of France from across the water. Trump, naturally, drew his native New York City in a stylized fashion.

The Kennedy painting, which more than tripled its $50,000 presale estimate, was the top lot at the December 2 Americana & Political Grand Format Auction. The canvas, thought to date from 1955, is signed and displayed in an ornate frame with a John F. Kennedy nameplate. It was consigned by a member of his family and was sold with a photograph of the president painting, as well as a note from its original owner, Kennedy’s sister-in-law Ethel, wife of Robert F. Kennedy.

This Donald Trump sketch of the New York City skyline sold for $20,000. Courtesy of Heritage Auctions.

The painting is one of just two known oils by the statesman, who also had a set of three watercolors of Sheepshead Bay sell for $36,800 at a 2013 auction at John McInnis Auctioneers in Amesbury, Massachusetts. (His other canvas is at the Kennedy Library in Boston.) Although Heritage attributes the lack of work by the politician to the fact that “JFK was not endowed with great artistic talent,” the work’s rarity likely helped boost its performance on the block.

In contrast, at least three other Trump doodles have already come up for sale this year. The works were all created for charity auctions, with the Heritage drawing donated to New York’s St. Francis Food Pantries and Shelters in 2005, where it went for $6,000. Ahead of this month’s sale, Heritage touted “the multi-color treatment and fine detail” in Trump’s drawing, noting that it was “superior” to his other explorations of the theme.

This Donald Trump sketch of the New York City skyline sold for $8,375. Courtesy of Nate D. Sanders.

Nevertheless, the piece failed to surpass the $29,184 brought in by another 2005 Trump skyline sketch at Nate D. Sanders in July. The Los Angeles auctioneer sold a second Trump skyline, from 2008, for $8,375 in September. The following month, Julien’s Auctions, also in LA, sold a doodle of the Empire State Building by the president for $16,000. Back in the 1990s, it originally sold for less than $100 at a charity auction at the ArtGras art fair in Palm Beach Florida.

“Nobody could have envisioned back then that Donald Trump would become president,” Heritage consignment director Don Ackerman told NBC. “So now all of a sudden you have something that was worth X number of dollars that is worth a whole lot more now that he became president.”

This Donald Trump sketch of the Empire State Building sold for $16,000. Courtesy of Julien’s Auctions.

Trump’s prices also benefit from the subject matter, especially fitting for the real estate magnate. “If he would have painted an apple, there wouldn’t be the same interest,” Pontus Silfverstolpe, co-founder of auction evaluation service Barnebys told the Huffington Post. “It wouldn’t be so him.”


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