Olivia's death in 1904 and Jean's on December 24, 1909, deepened his gloom.[2] On May 20, 1909, his close friend Henry Rogers died suddenly. In April 1906, he heard that his friend Ina Coolbrith had lost nearly all that she owned in the 1906 San Francisco earthquake, and he volunteered a few autographed portrait photographs to be sold for her benefit. To further aid Coolbrith, George Wharton James visited Twain in New York and arranged for a new portrait session.