Matisse’s only instance of double portraiture is a testament to his close friendship with Sarah and Michael Stein, Bay Area residents who were the artist’s most passionate American supporters.

Although the two paintings are nearly identical in size and format, they differ greatly in approach and effect. The portrait of Michael is the more traditional of the two, with its direct, frontal pose and limited palette of yellow ocher and brown with bold, black outlines. It was with Sarah that the artist achieved a bond which transcended that of patron and artist. “She knows my paintings better than I do,” Matisse is purported to have said.

When Sarah Stein began to slowly disperse her art collection in the years before her death in 1953, Elise Stern Haas purchased the portrait of Sarah and convinced a Chicago collector, Nathan Cummings, to acquire the portrait of Michael, with the understanding that both would eventually become part of SFMOMA’s collection. Mrs. Haas wanted the portraits to remain as a pair in San Francisco, in honor of her close friends and their role in bringing the work of Matisse to the Bay Area.