In 1889 Henry Walters moved to Wilmington, North Carolina, to serve as general manager of his father's railroad. Following William's death in 1894, he was elected president of the Atlantic Coast Line Company and transferred the line's headquarters to New York. Henry had an uncanny flair for business, and under his leadership the railroad experienced rapid growth until World War I, acquiring the vast Plant system in Florida in 1902 and taking control of the Louisville and Nashville Railroad in the same year.
In New York Henry Walters lived with Pembroke and Sarah Jones, a couple he had met in Wilmington. Seldom did Walters return to Baltimore other than to attend board meetings of the Safe Deposit and Trust Company. Three years after Pembroke Jones' death in 1919, Henry married Sarah and they continued living in the Manhattan house surrounded by fine French 18th-century paintings and decorative arts and earlier Italian works of art. In his New York library Henry Walters kept many of his most prized rare books and manuscripts and other treasures.
From the outset, Henry Walters envisaged a museum that would fulfill an educational role within the community. Initially he made modest additions to his father's collection. Benefiting from historical perspective, he enhanced the breadth of the 19th-century holdings with such early works as Ingres' Betrothal of Raphael, bought in 1903. Although he did not find French Impressionism to his liking, he agreed in that year to buy two examples from Mary Cassatt-a small Degas portrait and Monet's Springtime, an exquisite image of the artist's wife, Camille, seated on the grass beneath lilac bushes in their garden at Argenteuil.
That Henry's ambitions for the collection far exceeded his father's became apparent in 1900 when he bought Raphael's Madonna of the Candelabra, which had passed through both the Borghese and Bonaparte family collections. Also that year he purchased a number of properties on Charles Street, in Mount Vernon Place, to serve as a site for a future gallery.
Two years later Henry undertook an acquisition on a scale unprecedented in the history of American collecting: he bought the contents of the Palazzo Accoramboni in Rome. The collection abounded in works of significance, many of them by masters other than those to whom they had been ascribed, and others by artists not in fashion at that time. In the latter category fell El Greco's painting St. Francis Receiving the Stigmata. Among the collection's archeological treasures were seven magnificent sarcophagi from a burial chamber associated with the Calpurnii Pisones family, pieces that alone would have justified the purchase of the collection. Henry courageously agreed to buy the collection for the sum of five million FF or $1,000,000.
Henry Walters continued to augment his holdings, buying both in New York and abroad. Walters continued to collect Egyptian, ancient Near Eastern, and Islamic art, as well as a number of key classical and western medieval objects. Among the latter, the most spectacular was a pair of limestone heads of Old Testament rulers that had come from the abbey church of Saint-Denis. In 1897 the purchase of a 15th-century Koran, originally thought to be Persian, but now regarded as Indian, may have initiated the manuscript collection.
In New York, beginning in 1903, Henry Walters served on the executive committee of the Metropolitan Museum of Art, and 10 years later he became second vice president, a position he retained for the rest of his life. His experiences on a number of museum committees may have resulted in a change of direction in his collecting after World War I. Walters now appeared less concerned with acquiring works representative of various fields and more committed to objects of major historical and artistic significance.
Henry soon had the site of three buildings he had purchased in 1900 transformed in to a palazzo like building, which opened to the public in 1909. He died in 1931, bequeathing the building and its contents to the mayor and city council of Baltimore "for the benefit of the public."