Michelle Robinson Obama grew up on Chicago’s South Side with parents who taught her to be “outspoken and unafraid.” After earning degrees from Princeton University and Harvard Law School, she joined Sidley Austin LLP in Chicago, where she met the man who would become her husband and the forty-fourth president of the United States. Wanting to improve her community, she left the firm in the mid-1990s and transitioned to a career in public service. As first lady, she fought for women’s rights, children’s health, LGBTQ+ rights, andmilitary families. Obama selected Amy Sherald to create her portrait after Sherald won first place in the National Portrait Gallery’s 2016 Outwin Boochever Portrait Competition. The women formed a bond through their shared passion for inspiring young people, especially girls of color. Sherald, who is known for portraits of African American subjects painted in grayscale, asserts, “I always want the work to be a resting place for Black people, one where you can let your guard down among figures you understand.” Painted when Obama was writing her memoir Becoming (2018), this iconic portrait shows her in an introspective mood wearing a Michelle Smith dress reminiscent of the Gee’s Bend quilts made by descendants of enslaved people.