Henry W. Peabody, born in Salem on 22 August 1838, began his life in business at Williams & Hall, China and Indian merchants. He worked in the counting room there, and three years after he moved on to be a clerk at Samuel Stevens & Co. After three years in that position he became a member of the firm. Although Samuel Stevens & Company had established a large trade with India, Africa, and Australia, and seemed to be moving in a prosperous direction, the success of the company declined steadily over the next three years.
By 1866 Peabody had retired, having lost most of the money he had made thus far. By 1867 he had started his own trade business, Henry W. Peabody and Company, with offices in New York City, Yucatan, London, and Sydney. This business did very well and Peabody was heavily involved in all aspects of his company.
After Peabody had died, President Taft leased his estate as the summer capital. The widow who owned the estate Taft originally leased grew tired of the constant media attention and tourist traffic on her property, and therefore refused to renew the lease. Lucy W. Peabody, Henry’s widow, agreed to let Taft use her home for the second half of his term.