After her husband's death in 1931 Hale found herself in financial difficulty and after a number of unsuccessful relationships she committed suicide in 1938 by jumping from the top window of her apartment in New York City.
Clare Boothe Luce a close friend of Hale and the publisher of Vanity Fair commissioned Mexican artist Frida Kahlo to create a remembrance portrait in memory of Dorothy Hale with the intention of gifting it to Hale's mother.
When Kahlo unveiled the portrait in August of 1939 of the in depth depiction of Hale's death, Luce was so shocked she was quoted as saying the she "nearly passed out."
The portrait shows Hale in each stage of her suicide and even shows Hale dead on the ground surrounded by blood.
The text at the bottom of the portrait reads "In the city of New York on the twenty-first day of the month of October, 1938, at six o'clock in the morning, Mrs. Dorothy Hale committed suicide by throwing herself out of a very high window of the Hampshire House building.
In her memory this retablo, executed by Frida Kahlo." In Kahlos original also had the words "Mrs. Clare Boothe Luce commissioned" but we're later painted out at Luce's request after Kahlo delivered the portrait.
Luce never gave the portrait to Hale's mother and instead left it in the care of her friend Frank Crowninshield who kept it until his death when his son returned it to Luce's family who kept it in storage for some years. The piece was eventually donated to the Pheonix Art Museum.
It is speculated that the sombre depiction of Hale is due to Kahlos own thoughts of suicide during a difficult separation.