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Herbert MacIlwaine was The Espérance Club's second music director 1901-1907. (Emmeline Pethick-Lawrence being the first).

It is likely Neal and MacIlwaine met through their various connections to the Passmore Edwards Settlement in based at the Mary Ward House. MacIlwaine stepped down from the post in 1907 when he was unable to reconcile his the work with his lack of support for the growing suffrage movement and The Club's increasing association with it. Despite these fundemental differences of opinion, he remained a close acquaintance of Mary Neal's and on his death in 1918, requested she adopt and care for his then orphaned son, Anthony which she did.