In 1899, he helped fund the rebuilding, and became manager, of His Majesty's Theatre. Again, he promoted a mix of Shakespeare and classic plays with new works and adaptations of popular novels, giving them spectacular productions in this large house, and often playing leading roles. His wife, actress Helen Maud Holt, often played opposite him and assisted him with management of the theatres.

Although Tree was regarded as a versatile and skilled actor,