In 1905, buying adventurous works by young artists conferred no status. Acquiring what would now be called “challenging” art didn’t provoke admiration for being enviably ahead of the curve, but rather pity for questionable judgment. Sophistication and taste were signaled by acquiring the art of the past, which is why, in the late nineteenth century, wealthy Americans came to Europe to purchase the Old Master canvases that now enrich museums on this side of the Atlantic. A few progressive collectors of that generation, such as Louisine and H. O. Havemeyer, also made impressive aquisitions of Impressionist works and paintings by artists such as Gustave Courbet and Jean-Baptiste-Camille Corot, but the Havemeyers had the advantage of advice from Louisine’s friend Mary Cassatt and from Cassatt’s friend Edgar Degas.

At the start of the twentieth century, not even the most progressive American collector would have been likely to buy a shockingly unconventional canvas by a rebellious thirty-five-year-old artist (albeit one being written about as the leader of a new school of painting and promoted by forward-looking dealers), especially when that work struck him at first as “the nastiest smear of paint” he had ever seen.Yet that is exactly what Leo Stein did when he acquired Henri Matisse’s 1905 portrait of his wife, Woman with a Hat, from the “Fauve” room of that year’s Salon d’Automne, not long after he had settled in Paris with his sister Gertrude. Despite Leo’s initial reaction to the picture, he found it unignorable. He