Milton William “Billy” Simpson was one of Alameda’s most prominent early civic figures—a gifted attorney, state legislator, California National Guardsman, and well-known local personality whose life blended public service with private turmoil. His dramatic drowning, the chaotic scenes at his funeral, and the bitter litigation over his estate made him one of the most talked-about men in the East Bay during the spring of 1911.
Born in California in 1870, Simpson displayed an early aptitude for civic affairs and the law. He first entered statewide politics as a member of the California State Assembly, representing Alameda with a reputation for intelligence, vigor, and meticulous preparation. His political ascent continued in 1904 when he won a special election to the California State Senate, filling the seat vacated by Senator William Knowland, who had resigned after being appointed Clerk of the California Supreme Court—a prestigious statewide post conferred by the governor. Simpson served the remainder of Knowland’s unexpired term and established himself as a steady, independent voice in Sacramento.
Following his legislative years, Simpson became City Attorney of Alameda, a position he held for nearly a decade. He also maintained a long affiliation with the California National Guard, rising to the rank of major in the First Battalion, Fifth Regiment. To many in Alameda, he embodied the mix of civic duty and personal ambition characteristic of early 20th-century California public life.
Simpson’s promising career took a sharp and very public turn in early 1911 with the emergence of Isabella (or Isabelle) Davis, a young Alameda stenographer who accused him of seducing her under promise of marriage. Davis pursued him relentlessly through official channels, demanding recognition, marriage, or legal redress. Accompanied by her mother, she confronted Simpson repeatedly at the City Attorney’s office, insisting he had a duty—moral and financial—to her and to the child she said was his.![]() |
| Oakland Tribune, May 2, 1911 |
On April 30, 1911, Simpson joined his closest friend, Judge Robert B. Tappan, for an afternoon sail aboard the sloop Carrie L. near the Alameda Yacht Club. Both men were familiar with the vessel and the waters, and the outing was expected to be routine. But as the boat came about in a strong gust, the boom swung violently and struck Simpson, knocking him overboard. Simpson, an excellent swimmer, appeared either stunned by the blow or caught in the rigging. Judge Tappan desperately tried to pull him back aboard, but he was physically incapable. Years earlier, Tappan had lost his left arm in a railroad accident, a disability that now rendered him unable to rescue his friend. “I could not save him,” he told reporters through tears. “My God, I had only one arm.” Simpson drowned before help could arrive. His body washed ashore later that day, and Alameda was plunged into shock and mourning.
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| Oakland Tribune, May 3, 1911 |
Simpson’s will, executed in December 1910, stunned much of Alameda. He left $25 to his young son with Davis; nearly all remaining assets, including insurance totaling about $7,900, to his sister Edna Simpson; and appointed Judge Tappan executor. Davis immediately announced she would contest the will, claiming Simpson had promised to provide far more for their child. The dispute played out in the press with characteristic volatility. Although she fought vigorously, there is no surviving record that the will was overturned; Simpson’s estate appears to have remained with his family.
Milton William “Billy” Simpson’s life encompassed the best and worst of public life in the Progressive Era: political ambition, civic duty, scandal, violence, tragic accident, public mourning, and contested memory. His dramatic demise and the chaotic aftermath left an enduring imprint on Alameda’s civic history. Today he's remembered for both his accomplishments and the extraordinary turmoil that surrounded his final year.
Sources: Oakland Tribune (May 1–4, 1911); Sacramento Union (1911); Associated Press dispatches (1910–1911); Find a Grave Memorial 284571468; California State Archives legislative records.



































