From: Christie's (about the Sargent portrait of Casper):

While all of Newport angled for a meeting with the great European-bred artist, Sargent resided comfortably with his old friends, Admiral and Mrs. Caspar Goodrich, parents of the young sitter. Charles Merrill Mount describes Sargent's arrival in the United States: "He arrived at Torpedo Station huge and dominant, smiling and eager. It was years since he had seen the Goodriches, and since those peaceful days at Florence [Mrs. Goodrich] had borne a son, doubtless one day to enter the Navy, and a daughter, both of whom he would meet. It was pleasant to find friends in a strange place: Admiral Goodrich, who still spoke of the sea and ships as Dr. Sargent had. . . ." (John Singer Sargent, p. 106) Inscribed to the sitter's mother, it is presumed that Sargent's portrait of Caspar Goodrich was not a commissioned work, but a token of gratitude for the Goodrich's hospitality during the artist's stay.

Caspar Goodrich has enjoyed a long history of critical acclaim. In January 1888, shortly after it was painted, Caspar Goodrich was exhibited at Boston's St. Botolph Club along with some of Sargent's most celebrated pictures, including El Jaleo (Isabella Stewart Gardner Museum, Boston, Massachusetts) and The Daughters of Edward D. Boit (Museum of Fine Arts, Boston, Massachusetts). The show galvanized his already strong support by his American audience. Royal Cortissoz compared Caspar Goodrich favorably with some of Sargent's most celebrated pictures: "This likeness of a little boy in a sailor's suit is a charming interpretation of boyish character .... [in which] he has treated adolescence with the most searching understanding." (as quoted in W.H. Downes, John S. Sargent, His Life and Work, Boston, Massachusetts, 1925, p. 150)

The six year old Caspar Goodrich would have been an irresistible subject for Sargent. A beautiful young boy with a peachy complexion and dark eyes, Sargent painted him wearing a sailor suit, the most fashionable costume for a young boy throughout the nineteenth century. Capturing the boy with arms crossed, gazing directly at the viewer, Sargent conveys the impression of both mischief and good manners. Almost in spite of himself, a smile appears to be emanating from beneath the surface of the headstrong subject. Unlike their adult counterparts, Sargent's young sitters were unselfconscious and provided the artist with subject matter from which he derived some of his best work - enduring portraits that convey much more than the physical attributes of the subject.

(From Wikipedia): Caspar Goodrich, son of Rear Admiral Caspar F. Goodrich, was born in Italy. Goodrich was appointed a midshipman from Connecticut on 7 September 1897. He was designated a Naval Cadet 10 June 1901 and reported to Lancaster for duty. From 1903 to 1905 Goodrich served in Maine, Cleveland, and Chicago. Assigned to Georgia on the Atlantic Station in June 1906, Goodrich was killed 15 July 1907. He was the command officer of the after superimposed 8" gun turret when a flare back caused 104 lbs. of powder to explode behind the starboard gun. Ten men were killed, including Goodrich. Eleven men were injured.