Kahlo and her husband, artist Diego Rivera, had convinced government officials to allow Trotsky and his second wife, Natalia Sedova, to live in exile in Mexico.

[2] Many of her surrealist works depict moments in her life, often tragic ones, due to her tumultuous marriage to artist Diego Rivera and her recurring health issues.

Kahlo's personal life and her artwork were heavily influenced by the Mexicanidad movement, which seeks to revitalize the culture of Mexico's indigenous peoples.

[3][4]On January 9, 1937, Russian revolutionary Leon Trotsky and his second wife, Natalia Sedova, arrived in Tampico, Mexico, after living in exile for several years due to Joseph Stalin's success in ousting him from power.

[5][6][7] The couple welcomed Trotsky to take up residence in their Blue House (La Casa Azul), located in the Coyoacán neighborhood of Mexico City.

[5] Wilhelmina Holladay, co-founder along with her husband of the National Museum of Women in the Arts (NMWA) in Washington, D.C., received the painting as a donation from writer and politician Clare Boothe Luce.

[13] It has been loaned to exhibitions at the Inter-American Development Bank's cultural center, the National Gallery of Australia, and the McMichael Canadian Art Collection.

The latter focused on the works of Kahlo, Georgia O'Keeffe, and Emily Carr, representing Mexico, the United States, and Canada, respectively.

[8] Her outfit consists of a dress worn by Zapotec women from the Isthmus of Tehuantepec and was considered to be more subdued compared to other self-portraits.

Her top consisted of a huipil, a commonly worn item amongst indigenous women in Mexico and Central America, which is red with green trimming.

Kahlo's hairstyle resembles that of women from the Tehuantepec region, being braided and adorned with a pink flower and red ribbon.

[19] According to Josefina De La Torre from the Fashion Institute of Technology, "her ensemble blends late-30s beauty trends with traditional clothing.

Burchard interpreted the painting as a way of Kahlo showing her survival instinct in an art world dominated by men, including her own husband.

[14] Sarah Milroy from The Globe and Mail wrote that the painting demonstrates Kahlo's satisfaction with the affair she had with Trotsky, but noting the overall tone is tame compared to her other works.

[15] In 1938, Breton wrote about how deeply moved he was by the painting:[5] "I have for long admired the self-portrait by Frida Kahlo de Rivera that hangs on a wall of Trotsky's study.

[7] Author and historian Hayden Herrera believes Kahlo gave the painting as a way of teasing Trotsky, especially by being dressed "fit to kill" along with wearing makeup.