Two portraits of two generations of Rothschild women hung in the Jewish Museum of Frankfurt prior to World War II: a portrait of the Rothschild matriarch, Gutele v. Rothschild (1753-1849), and her granddaughter, Charlotte v. Rothschild (1819-1884), both attributed to the artist Moritz Oppenheim (1800-1882). The depictions of the women are very different, both in style and in content. Do these contrasts reveal changes in both the attitudes towards these women and the different roles they were to play? This paper will discuss these two depictions in the light of gender studies, the family’s history and the catastrophic events of the Second World War.