Dempsey–Willard Fight

Two boxers in a ring
Dempsey–Willard Fight | James Montgomery Flagg (1877–1960) |  Oil on canvas, 1944 |  Gift of Mr. and Mrs. Jack Dempsey

On July 4, 1919, challenger Jack Dempsey (1895–1983) met reigning champ Jess Willard (1881–1968) in an eagerly awaited bout for the heavyweight championship of the world. Having demolished a series of opponents to earn a shot at the crown, Dempsey was a decided underdog in the matchup with Willard, who was five inches taller and fifty-eight pounds heavier than his opponent was and considered unbeatable. Yet when the two boxers met, the contest was brief and brutal. In the opening round, Dempsey (in white trunks) unleashed a torrent of punishing blows that felled Willard seven times. By the end of round three, Willard was finished, and Dempsey was the new champion. He defended his title until 1926, when he lost to Gene Tunney.

More than twenty years after upsetting Willard, Dempsey commissioned his friend James Montgomery Flagg, a painter and illustrator, to commemorate the historic heavyweight contest. Flagg is well known for the posters he created during WWI, most notably his “We Want You” Uncle Sam poster. Prior to the commission, Flagg had painted portraits of Dempsey’s children, Joan and Barbara, which hung over the mantelpiece in Dempsey’s home.

On November 14, 1944, the Dempsey-Willard Fight painting was unveiled at Jack Dempsey’s Broadway bar and restaurant, where it occupied a place of honor until the restaurant closed in 1974. Notably absent at the unveiling was Jess Willard, who wired Dempsey, saying, “Sorry I can’t be there. But I saw enough of you 25 years ago to last me a lifetime.”

  • Imagine you can jump into this painting. Once inside, write down thoughts related to your five senses: sight, touch, smell, taste, and sound.
  • Think about which boxer represents Dempsey and which represents Willard. Given the pose of each boxer, who appears to be in a winning position?  Why?
  • How is this painting similar or different from other artworks by James Montgomery Flagg? How does it compare to his posters in purpose or design?
  • Consider what was happening around the world in 1919. What sorts of connections can we make between this painting and what was happening during the time when it was made?