Chester Dale came out of a reputable friendship Dale had with Diego Rivera. 

Chester Dale made his fortune in the stock market. In 1935 he retired from banking life and began a career as an art collector. Dale was known for becoming friends with artists, including Rivera and Salvador Dali, who both painted portraits of the avid art collector.

Dale lived life in the fast lane. He was born on Boxing Day, 1883 in Manhattan and started off as a messenger on Wall Street after dropping out of military school in 1899. The messenger gig lasted a week. Dale moved on to work in an investment house where he got a taste of playing the stock market. Some time in his youth he was even a boxer. At twenty-seven he married Maud, who he was lucky to have in his corner, an art historian and painter she knew a thing or two about the art.

In the early 1940s, Dale took a trip down to Mexico to visit the international superstar artists Diego Rivera and Frida Kahlo, who had yet to achieve the fame for which she would be known. Diego and Frida had recently married and they were living in the Blue House in Coyoacan, Mexico City. 

The Chester Dale Collection of art consisted predominantly of French pieces. It was Maud who lectured Dale about the significance of French art. Their collection included works by van Gogh, Matisse, Renoir, Picasso, Manet, and so much more that it seemed this man rubbed a genie’s lamp and was granted his wishes. Their collection contains over 300 artworks. 

Dale was a family man, but not the orthodox type. His children were the works of art he and Maud collected. Upon his death in 1962, the children were given to the National Gallery of Art with the conditions that they would be displayed all together in a gallery bearing his name, and they would never be loaned out. The family stays together always and forever.