Senator James D. Phelan befriended Wills and invited her as a frequent guest to his estate, Villa Montalvo. Wills wrote poetry as a hobby, and presented two of her works, "The Awakening" and "The Narrow Street", to a literary competition hosted by Phelan in 1926. Wills settled laurel wreaths over the heads of the winners. Phelan himself wrote a poem dedicated to Wills. In 1928, Phelan commissioned Haig Patigian, sculptor and fellow member of the Bohemian Club, to create a likeness of Wills. Patigian completed a marble bust of Wills in October 1928 called "Helen of California", and Phelan donated it to the M. H. de Young Memorial Museum. At his death in 1930, Phelan left Wills $20,000 ($ today) in his will, "in appreciation of her winning the tennis championship for California".