The William Osler photo collection was begun when Sir William Osler's widow, Grace (1854-1928) invited Dr. Harvey Cushing (1869-1939) to write her late husband's biography. As a student at Johns Hopkins from 1896 to 1900, Dr. Cushing was befriended and encouraged by Sir William, who nurtured a love of medical history and books in the younger man. Despite being a very prominent and busy neurosurgical pioneer, Dr. Cushing agreed to write the biography. He canvassed far and wide for recollections of Osler and letters from him. By publishing requests in major newspapers and medical journals, writing letters to anyone who knew Osler, and visiting the homes of Osler's family members, he amassed a large collection of papers and photographs chronicling Osler's life. The Life of Sir William Osler was published in 1925 and won the Pulitzer Prize in 1926. In 1932, Cushing deposited this collection at the Osler Library in Montreal.

During his lifetime William Osler had amassed a library of about 8000 rare medical and scientific texts. This library was left to his alma mater, McGill University, at his death, and this was the beginning of the Osler Library of the History of Medicine. W. W. Francis (1878-1959), the first Osler librarian, was himself a collector of Osleriana, and when the Cushing papers were deposited with him he did not treat them as a finished collection. Rather, he continued to add photographs and letters and other documents that he had retrieved. The practice did not stop with Dr. Francis' death in 1959, and the collection continued to grow. Thus, the "Cushing papers" contain much that Cushing never saw — not unlike the Osler Library, which continues to add new materials around the core of the books that were purchased by William Osler himself.

At some point in the history of the Cushing papers the photographs were separated from the letters and documents. Attention began to shift away from physical collections and toward electronic access to library and archival material. Continuing interest in William Osler's life, along with the comparatively small size of the Cushing collection of photographs, made it an ideal subject for digitization, and the William Osler Photo Collection was created under the auspices of the McGill University Library and the generosity of the John P. McGovern Foundation.