In 1907, Brinkley settled with his wife in Chicago, where they celebrated the birth of a daughter on November 5 – Wanda Marion Brinkley. The new father enrolled at Bennett Medical College, an unaccredited school with questionable curricula focused on eclectic medicine. Brinkley worked for Western Union as a telegrapher at night and attended classes during the day, while debts mounted from tuition, the cost of raising a family, and from Sally's self-centered whims. In 1908, the Brinkleys buried an infant son who had lived only three days.